What Not To Wear After Age 40

When I first started writing about fashion for women over 40, I researched fashion for women our age. I bought some books, and I read them from cover to cover.

 

I learned a lot from reading those books, but now that I’m well past my 40s, my thoughts on what not to wear have changed.

You should wear what makes you feel good. Dress your body type. It’s more about what looks good on your body and less about a number (your age).

With that being said, there are some things that you might what to think about if you’re over 40.

Here is my list of What Not To Wear After Age 40 

1. Jeans that don’t fit. While baggy jeans are coming in style again, they aren’t very flattering. Good fitting jeans look good on any age woman.

Moto Jacket (I’m wearing a small)//Button Up Blouse (I’m wearing a small)//Abby Ankle Skinny Jeans (I’m wearing a size 4)

It’s always a good idea to check our jeans’ backside to see how they look. I shared 5 Brands Of Jeans And How They Look Front And Back.

2. Dark Lipstick can make your teeth look whiter, but it can also be harsh and accentuate fine lines. As you age, you might want to wear lighter lip color.

Maybelline Warm Me Up #235 is a beautiful color that looks good on most women.

Classic Cardigan (I’m wearing an XS)//Black Corduroy Jeggings (I’m wearing a size 4)//Leopard Flats (TTS)//Charm Necklace//Ivory Tank (similar here)

3. Obvious lip liner is not attractive at any age.

4. Holiday Sweaters with bells and appliqués are fun to wear to an ugly sweater party but stick to classic sweaters in red or green for a sophisticated look.

5. Black hair color is harsh, and most women over 40 look better with a lighter color. It softens your overall look.

My hair is a medium brown color with some natural highlights.

6. Glittery eyeshadow can settle into fine lines, but a little shimmer in the right places is a great option.

7. Outfits that are too matchy-matchy. Right now, they’re having a moment in the fashion industry, so wear them if you like them, just don’t overdo it.

8. Elastic waist pants or shorts. Elastic instantly ages you, so anything besides work-out clothes should have a regular waist.

This is not an exhaustive list but a list of things I try to avoid. Never say never when it comes to fashion because it’s always changing.

Growing older doesn’t mean you can’t have fun with fashion. Enjoy every season!

Rain Parka (I’m wearing a size 00)//Contrast-Stitch Top (I’m wearing a size 00)//Soft Skinny Jeggings (I’m wearing a size 00)//Earrings//Scarf (not online)//Sam Edelman Heel

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Beauty For the Heart~~She is clothed with strength and dignity, and she laughs without fear of the future. Proverbs 31:25

Have a blessed day!

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  1. Thank you for your tips on What Not TO Wear after 40. I am now 60 with 2 grandchildren. I use your tips all the time to help me NOT look too old. Thank you! Also, you are SO right, keep God first in your everyday life, no matter how big or small.

    P.S. In your opening of this you have a typo. It says you might “what” to think about and it should say you might “want” to think about.

  2. I have followed your fashion expertise for a couple years now. Even though I am a young 62 I get a lot of good fashion tips from your various platforms. During this pandemic I have especially loved following your fashion tips. Someday when we can all move around freely again, girl, I’m going to be ready and fashion forward with your wonderful suggestions.

    Thank care Cindi

  3. Love reading your post everyday!! I’m 61 and want to be stylish but not look teeney bopper!! Love your outfits!! You have a precious figure and look great in the clothes you wear!! I teach school in Texas and we don’t dress up much in our little country town! Thanks for giving me lots of fashion ideas!
    Sincerely, Dianne

  4. Love this list and totally agree. I’m a new member of the 50’s club and although I feel great and am told I don’t look 50, I have no desire to dress like I’m in my 20’s! There is too many fabulous, classic, timeless fashion choices (and always a trend to be pulled off)! Love all your suggestions! Thank you for sharing!!

  5. Enjoyed this blog, What not to wear after 40.
    I am a few years past 40 and have always agreed with wearing what you like, feel good in as well as what looks good on you. Having a teenage daughter helps me keep within the “fun mom” looks rather than the “that looks like what grandma would wear” look. She definitely helps when I check to see if this “fit” is okay. I truly enjoy having fun with fashion.
    If you have any girlfriend/boyfriend Jean outfit ideas for winter weather I’d be curious to see them.
    I like the relaxed feel for those “feeling fat” days. Lol.
    Thanks!

  6. These are all good tips and I think most of them can apply to women of any age. But speaking of age, I look to blogs and vlogs for advice and encouragement regarding staying stylish and on trend without looking like “mutton dressed as lamb”; however, I am done being told “you can’t wear this or do that because you are over age __”. Especially with the past year filled with stress and negativity. I would much rather see advice on how to look fashion forward at any age. I know how old I am and don’t need to be reminded of it ad nauseum.. So, from now on when I see that in any heading of I am just going to move on.

  7. Yes to the baggy jeans! My daughter told me my jeans looked awful and they weren’t even very baggy! I got new skinny ones, and jeans are so stretchy and engineered so well these days, they are very comfortable and make me look 10 pounds thinner!

  8. Great advice. I am 63 years old…never have and never will wear elastic waisted jeans. My generation embraced jeans and I will never embarrassed that awesome 70’s generation. I love your faith based words and fashion advice. I can honestly say…I don’t look or feel 63 but I am thankful to be here. God Bless

  9. I’m beyond my 40’s and will add on this thought…don’t try to look like your teenage/20 something daughter….ya don’t have to dress like your grandma but come on…hehehe

  10. Cyndi, thank you for sharing this! I think is is always helpful to be reminded of some of these things. Thank you for doing what you do to help us, your followers look our best! Don’t let those negative comments get you down as many, many of us think you are just great!

  11. Can you do a blog on what’s out of style? I have a couple pairs of jeans with the fringe on the bottom that I love (you are wearing a pair with the pink coat) Are they out of style? Thanks!

  12. I’m well over 40 and love your blog. You look beautiful in all you wear. I’m someone who still wears the baggy clothes due to my size and not showing off my ugly curves and bumps. And while my clothes are baggy, they are not sweats and t-shirts. I dress very professional for my job, but just more on the baggy side. As I said, I love your posts. I was wondering if you knew of a blog like yours for heavier, curvier girls. I’ve searched but have never found one.

  13. Love your tips. I am 70 years young and I wear Maybelline 24 Stay Color #245, it does not feather on the lip. My opinion as you grow older natural hair color better suits your skin color. Mine is Salt & Pepper with more salt in the front. The thing is to keep the cut young and current. The only item I have really changed is my shoes. Went from 2-3 inch heels to sexy flats, yes there is such a thing. Thanks for all of your suggestions and tips to be a better you as we age. I’ve learned a lot from your posts.

  14. Your lip colour looks so pretty & natural. Is it a warm pink? I always wore Maybelline pink pop until they discontinued it recently & haven’t found a good replacement. Cool tones look best on me. Thanks.

  15. Cyndi——your style and taste is always appropriate in my opinion. Your pink/red coat from Kohl’s is double darling on you! I love your blog, and I say, keep up the great work! Thanks for your efforts!

  16. This was a good list but elastic waist skirts are just fine. They do not make you look older. I never wear pants or shorts so I can’t attest to those.

  17. Please, please tell us your hair color system – if you get it done in the Dallas area, where? If you do it yourself, how? It is gorgeous!!

  18. I have been following your blog for about 5 years…I enjoy your style choices and sometimes think something may not be right for everyone over 50.

    I just read the comment that lip liner never looks good…this one I would disagree….as we age, some of us may have lost a little of the color definition on the lips. Find a good make up lady…They can find a shade that looks like your natural lip. I wear a neutral shade and it just keeps my nude/natural lipstick from looking like it is faded. I never say never ..lol

    1. Well, she actually said “obvious lip liner” I wear lip liner bc I have lost color definition, but my color is the same color as the liner.

  19. Cyndi – love your advice, suggestions & prayers –
    Now, I get to be 70 – a blessing many don’t get the chance to be
    I so enjoy clothes & shoe shopping, along with trips to the hairdresser & mani & pedi stops
    We need to wear what makes us feel good – love checking on all the over 40 & 50 looks on Pinterest – I Always come back to your blog Cyndi, but sometimes I just want to check out what Maye Musk is wearing😃
    Thanks for all the fun fashion advices & links to purchase – great fun !!! Keep up the great work & God Bless – love, Rose ……..

  20. I find as I get older I don’t like running or shopping all over the place to try to put an outfit together. Could you do some one stop shopping blogs where the whole outfit comes from one place? I feel like I have a whole closet full of mismatched items.

  21. Morning🥶 Big snow storm here in Boston!! Great post! Thank you! Would you take some pictures with your new puppy? Have a great day!

    1. Loved your article on What not to wear after age 40. I could not agree more most of your advice. the baggie Mom jeans was my favorite.
      Thanks for always lifting my spirits, and reminding me I am not alone.

  22. I bought the Maybelline Warm Me Up lipstick after seeing your recommendation a few weeks ago and love it. Thanks for your emails and blog. I look forward to hearing from you every day!

  23. Good list! We all know 50 year old ladies who look 65 and 50 year old ladies who look 35. Most of us don’t want to wear things that make us look like we’re trying too hard to look young (chances are we’re not going to look the same in something as a 21 year old does) or that look frumpy (don’t dress like your grandma did at that age) Your common sense approach is encouraging. Happy 12th Blogiversary!

    1. Very true, I’m 59 and notice old high school class mates illustrating this observation. Some look so old with very short, old lady hairstyles that make me shake my head. Others have more current styles and look so much better. Same with clothes, baggy old lady jeans and Kohl’s sweaters and tshirts are not flattering to anyone.

  24. Thanks Cyndi. I appreciate your thoughts on this subject and love the way you encourage women to just be their best! Hope you’re doing well!

  25. Great List! I think beyond 40 – most women – start to know what is their best look, and are smart enough to follow fashionable women like you. We all have our “thing” we are willing to spend our dollars on and that may differ from what our friends do. A good friend or daughter 🙂 in my case is always willing to tell the truth. As a brunette most of my life, I always said I would never be blonde, and here I am at 57 with almost all blonde/gray hair. My grey is not the pretty silvery gray, it is the ugly (my opinion) yellow looking gray, so I have high/low lights put in to blend the yellowy gray – it works for me. Frankly I can’t imagine being the “dark brunette” I was when I was 25 – I look at your hair and I’ll admit to envy there bc it is BEAUTIFUL!

  26. Congrats on blogging for 12 years, WOW!! Hoping for 12 more! I love your posts, they are a bit of sunshine on a rainy day! And I love that you always include Beauty for the Heart, think that’s my favorite part! We all need to dress the inside same as the outside! Keep ‘em coming!! 68 & I’m feelin goooooood!!

  27. Love this. When I turned 60 I threw out my entire closet of clothes and bought new to celebrate. I asked myself, ” What does 60 look like? And what does a 60 year old wear? ” I ordered all young and stylish outfits, also bikini Leopard undies and etc… What fun!!!!!!!! And my hubby loved it!!!!! We must keep on keeping on!!!!!!!!!!!!!!

    1. I love it!!! I did something similar; the new clothes made all that old stuff look a bit frumpy and dated. It boosted my confidence (recently divorced) and caught the eyes of several of my coworkers. They are now upping their own games!

  28. You are the first blogger I followed, Cyndi! I’ve so enjoyed your fashion advice, Christian wisdom, and just your kind ways. Thank you for sticking with it – you’re one of the best!!

  29. Great post! I just turned 53 yesterday and have found myself more confident in choosing fashion in my 50’s. I know my body and what works and what doesn’t and what I’m comfortable wearing and definitely what’s age appropriate while looking and feeling great;) I love your blog as we share the same style. A great source! Thank you!

  30. I am 62 and feel I dress better now versus years ago. I attribute a lot of my change to you and your blog! So I thank you!

  31. Always love getting the daily emails from you! Love the fashion AND the inspirational verses. Can you do a post about how to cuff/roll your jeans when wearing either boots, sneakers, heels, etc?

  32. I agree with your tips. Every woman should have a full length mirror and a friend that loves them enough to tell them “that does not look good”.

  33. Here are a couple of ‘rules’ of mine. 1. tights are not pants, and 2. if you are going to wear leggings as ‘pants’, make absolutely certain that your top covers your ‘assets’, as it were.

    1. I agree; I am shocked frankly at some of the younger bloggers who are wearing leggings and cropped tops – granted, most are stick skinny but even then I don’t think it’s a good look. and I’m seeing women around town following this look…IT IS NOT GOOD! I guess I’m old fashioned but there is WAY TOO MUCH info being shared with this type outfit.

  34. I’ve got a few months to go before I’m in my 40s but I say: No rules. If you love it, wear it!! If it conflicts with the situation, environment, or whatever, be prepared for and accept the consequences but be true to your heart and be your authentic self. Don’t avoid wearing something because someone else says you shouldn’t. Own it!! Love it!!

    1. I totally agree! Be yourself. Pleasing others and society should be a thing of the past! Love and enjoy who you were meant to be. We’re all unique in our own way, which should be expressed creatively.

  35. I am 62 .I have my own list. 1. No grey roots. 2. Get a better bra. 3. Don’t wear glasses all cock-eyed. 4. Clean your glasses. 5. No nose hairs or mustaches. 6. Check your teeth for lipstick. 7. No cracked heels or hairy legs in sandals. 8. Pantihose are needed for dressier outfits. 9. Spend as much as you can on your teeth, skin cream, hormones, cosmetics, and hair.10. Have a best friend who reminds you to do all of the above.

    1. Great list…..except…..i decided I had better uses for two hours of my time and $120 then coloring my hair….au natural for me….no gray roots!!

      1. Who pays $120 for hair coloring. That is what a girl friend is for these days. Lose some pounds and fell vibrant. Wear one splashy colored outfit to go shopping. Have fun with life, it’s too short not to have fun.I am 74 and hope the Lord will still love me and watch over me for a few more years.

        1. I love your comment! I turned 70 last October, can’t believe it…lol. I wear what I like, feel comfortable in, and makes me feel good. Life is too short.

    2. Indeed. Well said. May I add, no chipped nail polish and NO flip flops unless you are on the beach. There are plenty of fashionable sandals out there for cheap.

    3. I totally agree. I am the same age and it’s generally good grooming that people forget. You can get away with a lot if you’re well groomed. With the right underwear!

  36. You nailed it! I’ve always been extremely conservative in style. Actually, now that I have passed 40 (way passed), I am actually dressing with style and enjoying every moment of it. Your “do nots” are in no way restrictive. But I’m having fun with clothing now. I think it’s because I have finally become the real me. I love your pins, love the colors, styling, everything. Thanks for all your wonderful suggestions and hints!!

  37. in the 2015 photo, you look 5 years younger & 10 pounds lighter! I agree with all your advice, except the dark lipstick. Some women over 40, especially those with darker skin, can still do dark lipstick. ?

  38. I stopped wearing foundation and instead wear a tinted moisturizer. I’m also in agreement with the poster that said that less is more. I’m very comfortable getting older. Knowing that God is in control takes so much stress from our lives. Stress can only cause us to look and feel older. Have a blessed day. Joi

  39. I think in your 40’s, “less is more”…. I also think it’s a good time to really zero in on your style…I’m a “preppy”…. so, I stock up on great sale item pieces from stores like Talbots and Lands End… with Preppy, you have to be careful to look like you are not repeating the 80’s! so, I skip the Garanimals look….I may match shoes and shirt…but not shoes, shirts, pants… I also think its important to let go of SIZES…. wear what FITS… tailor, or don’t buy, what doesn’t fit! take along a trusted friend to give you an honest opinion…and keep receipts! we all make regret purchases, but we don’t need to keep them!
    finally, don’t wear a bitter, downcast spirit! that’s the ugliest thing of all… wear love, joy, peace, patience, kindness, goodness, faithfulness, and self-control! those make us beautiful on pony-tail, elastic pants, no make-up days!!! because we all have them 🙂

  40. I love your 2015 look. I am well over the 40’s ….a little bit over 50 and just growing into my style. I often pin ideas on pinterest and then when I go shopping look for items similar. The thing that really helped me was to get my colour and style done by a consultant. I am not a slave to what she said but it makes a huge difference. If only I had that info when I was single then maybe when wearing that very bulky gathered skirt the little kid on my teaching practical may not have asked when my baby was due….and I would have saved a lot of money and time.

  41. Totally agree with every bit of this! Never say never, but it’s good to have some “ground rules” when it comes to fashion, especially as we get older. And WOW, girl, you looked fine in 2012 but you look AMAZING now. (I also cringe when I look at my older outfit pictures. I was thinner, but I sure looked awkward! LOL!)

    1. Lol! I sometimes wonder what I was thinking when I first started my blog! I’ve deleted some of my older posts, I couldn’t stand looking at them. 🙂
      Happy Memorial Day,
      Cyndi

  42. Do you ever feel frumpy and tired looking? I am in such a funk and thinking of changing my hair. Would love to see how you style your longer hair in different ways, you mentioned a pony tail before. I don’t think wearing my hair up is flattering anymore, especially since I have to wear glasses. I think I am afraid of having boring hair that I can’t do anything with but the one look. My hair dresser keeps getting my hair lighter and lighter blonde then when I say something she goes the opposite extreme. Ugh!! Add that I am a plus size woman,almost a misses size but just can’t loose enough to get to regular sizes. All that keeps me so frustrated. Any advice for my funk!! It’s a sin to be this self focused. 🙁

    1. I would say, try a new hair stylist. Usually good ones will give you a free consultation. Maybe you just need a new eye.
      Don’t worry about your size…dress for the size you are and do not be afraid to spend the money on something you like. Remember most items do not fit women perfectly so find a tailor. I have found this helpful if you are between sizes. Get the larger size and have it tailored.
      If you are trying to lose weight..start small. Choose one thing a week to do..like taking a walk everyday or drinking 5 glasses of water each day.
      Best of luck. I have been in a funk too, I know the feeling.

    2. Believe me Debra we all get in a funk. You might want to find a new hairdresser and I would recommend getting a makeover at Sephora or at one of the beauty counters in the mall. That always helps me!!
      Blessings,
      Cyndi

    3. Hi – Debra – sometimes we have to have a bit of ‘me’ time and its not a sin! Im 54 in 2 months and feel a bit frumpy and self-neglected – I’ve been scraping my collarbone hair up into a ponytail/bun for years now and I would advise…do not do this! Have a nice haircut instead. Also – spend some time on yourself. You are as important as all the other things or people you spend time on.

    4. I feel that Debra! This has been a good year for frump! I had all my hair cut off and I love it. Honestly, thank God it looks ok, cause growing it out would be hard. It really helped my attitude, though. I am definitely committed to trims every 5 weeks, so it’s a little pricey, but I feel a lot better about myself. I also get my nails done at the same time. They are a lost cause, but they look good for a few days. Now that I am older, I most regret not loving myself more (just as I am). I am trying to love and accept myself as God does.

  43. I would add to your list 11) really blonde hair and 2) skinny strap tank tops worn by themselves instead of underneath something as a layering piece. Often woman go braless in these tops and it just doesn’t look flattering.
    My hairdresser recently commented that it isn’t always the length/style of hair that can be aging, it’s the frizz. I live in a rainy climate and doing this can be tough, but I realize she is so right! I am 50 and don’t really look it, but certainly look older on those days when I don’t take time with my
    hair.
    The way I do some of the more trendy pieces is to try them on at the more expensive stores, then look for something similar at places like Old Navy, H&M or Loft on sale. That’s how I’ve come to have a few pair of “joggers” and love wearing them with cute sneakers or even flip flops?.

  44. I had to laugh at the Christmas sweater comments. I taught kindergarten for many years. I rocked those sweaters and “teacher clothes” back in the day. I stopped wearing them when my oldest child (3rd grader, mind you) asked if I was going to run errands after school “dressed like that”. I knew in that instant I wasn’t the cool teacher mom anymore. I had sweaters and jewelry to go with every holiday! Now my wardrobe consists of classic pieces. Love your blog, Cyndi!

    1. Oh, yes, Kathy: sweaters and jewelry for every holiday! And teacher button covers and collars and so on. ? You’ll laugh at this story: for Children’s Book Week, I always wore a shirt for whichever book we were celebrating that day. One night we were rushing after school to attend our daughter’s college recital, and I realized on the way that I was wearing a shirt with ARTHUR sewn on the front! We had to make a quick stop at a Walmart so that I could buy a shirt quickly and change in the restroom so as not to humiliate my daughter! ? Teachers have their own style! Or at least we used to! ?

  45. Wow, so many great comments to scroll through!
    I had to comment on the panty hose. I don’t wear them except for in the winter and recently when my step-daughter got married. I felt it was more appropriate to wear them at the wedding.
    My biggest issue is hair length! My husband loves it long but I am always wondering…
    I personally dislike excessive cleavage and yoga pants.
    I love your blog! Keep up the good work! 🙂

  46. I love your list. LOVE it! I am loving my forties and appreciate the fashion guidance you provide as my sons are high school age- and I finally feel like I can look stylish without *trying to look like the girls in their class! ha! You’ve saved them – and me! – from embarrassment! God’s blessings on you as you continue to touch the lives of women everywhere! Keep the good advice, tips, and shopping links coming! 🙂

  47. Cyndi, I love your articles, too! I am more of a classics first, preppy girl, so I have trouble choosing and justifying the expense of trendy clothes. And there are so many choices. How do you know which ones to try or buy? Having taken an “early” retirement, fiances are tighter than before so I want to make good choices. I also tend toward minimalism, so you can see my dilemma…thanks for any advice you can give.

  48. Love the list, but the comments are even better?. I am 47 and have always been a little out of the box. As I have gotten older I have added classic pieces, but I have to keep it a little funky to be me. I think it is most important to dress in clothes that make you feel like yourself and are flattering to your body type so you feel good in them. God made us all different, we are a beautiful bouquet of flowers (who will never wear Mom Jeans!) ? thank you Cyndi, LOVE your blog!

  49. Thanks Cyndi…..you look great in 2012….but you look AWESOME in 2015. That is one of my favorite outfits, the top is so flattering! Thanks for the list….I agree with ALL (although I am a tad guilty of the elastic band shorts/pants – they’re way too comfortable) 🙂 Have a great weekend!

  50. Laughed at the list…hope most go without saying!
    I think a well fitted bra should be added to the wardrobe must haves. It makes all the difference in the world- no matter what your size. I would love to see a do and don’t post on appropriate bras for our age group. A good bra or the right bra defenitely can make an outfit better. ( think about Cyndi!)

  51. I agree with your list but I want to add that I am not finding the skinny jean fad to be very flattering to most people. I like a more tapered jean and fortunately have been able to find some of those. Like some other older commenters (I am 65) , I have recently lost weight and that sure makes shopping for clothes a lot more fun. I do enjoy your blog as a way to keep up with fashion in a way that those fashion magazines can never do. (Does anyone really dress like that!!? I do live in a casual part of the world: Ann Arbor area)

  52. I love the list…and mostly agree.
    Yet I ultimately feel you should wear what allows you focus on others- what I mean is clothing that is comfortable, doesn’t need frequent adjusting, is not shifting to low or too high for modesty- don’t let clothes be a distraction or steal your attention in a situation….put on super cute clothes and head out the door into the Lord’s world to show his love and goodness and mercy, and try to not think of how you look …until the next day when you choose the next day’s super cute outfit:-)!!!!

    1. Suzanna, I love that you added this great point! It’s really not about us, it’s about honoring Him and loving others.

  53. Hi Cyndi: Love your look in 2012 and 2015… you are so fashionable! Your NOT To WEAR list made me smile…I agree with a lot of them EXCEPT elastic waist slacks/shorts and darker lipstick…I have some super cute Bermuda shorts and dark wash jeans with elastic and I love them! I also wear a rose/mauve lipstick that is dark pigmented and it looks great with my skin color.
    I would add no ripped jeans, no sweatshirts with Peter Pan attached collars, no sneakers with Velcro closures, no bright blue eyeshadow, and no midriff baring tops.
    But…I am in favor of women supporting, not shaming, other women…so I say if it makes you happy and you are comfortable/confident…then you ROCK your own style!
    Blessings!

  54. It’s funny about your rule of no Holiday Sweaters with bells and appliqués. For years, as a teacher, I LOVED wearing those sweaters to school. My young students loved them, too. I bought them after Christmas at good prices and had quite a collection. Then after many years, I noticed that I was one of the only teachers wearing them. That was about the time I noticed that most of the teachers were now the ages of my daughters. ? Then came “Ugly Christmas Sweater Contest Day” where they gave out prizes. I quit wearing them then. But, you know what? I may wear them next year. I’m almost 63, and I’m nearing retirement, so if the children and I like them, why not?! ?.

    1. Suzanne, I had to chuckle at your comments about the Christmas sweaters, you are telling my story. I retired from 33 years of teaching last June. Cyndi, I so enjoy your blog.

    2. I’m not a teacher, but always loved Christmas sweaters. That is until each Christmas while my daughter was in high school, she kept borrowing one of my faves. Finally, she mentioned it was always for the Ugly Christmas Sweater contest or party, as though I knew lol!

  55. Pantyhose are definitely in! Princess Kate has brought them back. I wear the Berkshire brand – very sheer and nude (can’t think of actual color name). There is nothing worse to me than seeing a professional woman who has jammed her bare feet into a pair of pumps. Yuck! Recently, I attended a program in the auditorium at a college. The college president, a mature woman, came up on stage to receive an award. She was dressed in a lovely suit. She had bare unshapely legs with the flaws exacerbated by the lack of nylons. I wear suits to work on a regular basis. I always complete my look with nude hose.

    1. Hi Cathy,
      Thank you Kate! I love her style. For me a sheer hose brings it all together. Some women look great without hose. My preference “yes to the hose”.

    2. I said a glad good riddance to panty hose years ago and have never looked back! There are so many wonderful leg creams, self-tanners, etc. I use one that adds a sheen that just makes my legs look so silky. I cannot even think of one friend, or co-worker who wears them any longer. So much more comfortable to go bare leg! 🙂

      1. I agree, never bring them back! I hate them and feel like I’m being tortured wearing them. Kate us adorable but she can pull off anything!

    3. I agree that hose look much more professional and put-together for certain occasions. I would rather wear pantyhose than deal with creams, tanning lotions, etc. Bare legs are fine for the beach or when it’s a very casual affair or when you’re going to be outside in hot weather, but hey, I live in Wisconsin so it only gets really hot here for a few months. And all the restaurants and stores here are freezing with the AC running full blast.
      Also, I have bumpy veins so really don’t have much choice. I went to a funeral recently and ALL of the women, except one, were wearing hose. But if I had really great legs, I have to admit, I probably would never wear hose. 😉

      1. I agree…my legs leave much to be desired! Pantyhose on occasion are my best option…wish I could get the leg issues fixed but finances and health issues make pantyhose a good choice for me.

  56. Lots of good advice in those rules! I love my fun, funky nail polish colors. Some may think I’m too old at 52, but I’m ok with that! . I have also decided to stop coloring my hair and let my natural color come shining through. Which is mostly gray. My 14 year old son was horrified, lol! I told him, it’s not going to be “old lady” hair, not short and frumpy ?

    1. If any of you are thinking about not coloring any more, there’s a great group on FB, Gray and Proud. Lots of encouragement there ?

  57. Cyndi , you don’t have a thing to cringe about. You are always beautiful and graceful in every picture!?

    1. I’m 55 and my parents grew up during the depression, so ripped-holy-paint/bleach splotched jeans were for painting or gardening…not to be worn in public. With that said, I was at a Jars of Clay concert when ripped jeans were becoming popular. The lead singer had on a pair of ripped jeans and before I could stop my ADHD mouth, out comes…” Oh honey, you make enough money to buy new jeans”. Well mom & dad, you ingrained your clothing values well….whether I agree with them or not.

  58. When my grandma was my age (late 40’s), I remember her wearing house dresses (you know those big baggy ones that you can still see on reruns). I do wear darker lipstick because it matches my coloring (with brown hair, brown eyes, and olive skin), but I assumed by dark lipstick, you meant the goth blackish lipstick. I’m glad fun nail polish colors, like blue, didn’t make your list because I’ll probably still be wearing fun nail colors when I’m 90, Lord willing. Thanks for all you do!

  59. I agree with your top 10 list and also enjoyed reading all the comments. I don’t see anything wrong with black hair (I’m blonde) if this is/was a woman’s natural color or their skin tone can handle it. Speaking of hair, bright red/orange hair or purple and blue streaks is unbecoming at any age and certainly not appropriate for women over 40. Likewise, I don’t think tattoos look good on women over 40. It looks like you’re trying too hard to fit in with the younger generation and some things just need to be left for the younger set. However, this is my opinion and not all will agree. I read this the other day and couldn’t agree more: “I don’t have any tattoos for the same reason you don’t put a bumper sticker on a Ferrarri!” 😀 Sometimes we just gotta make light and laugh at what’s popular!

    1. I love the quote…I regularly say it like this to my students (high school kids) , “You don’t put a bump sticker on a Benz!”

  60. Ok, seems lots of people have opinions on this. 🙂 me included. I read a fashion article the other day that hose are back IF they are sheer & nude. They specifically mentioned DK brand that is new with the nudes. I like hose with short dresses which I don’t often wear. I am in my 60’s. As for flip flops there are beach flip flops & casual flip flops. I love casual for errands etc. I agree with your list except I do have a few lounge shorts/pants with elastic for around the house. You look great, Cyndi. Better than 2012!

  61. Thanks for all of your good advice. I do like dark lipstick on occasion but not for the office or daytime wear. I love a dark lip with pale-ish skin. I probably look ridiculous but I like it anyway – ha! Keep up the good work!

  62. As a 33 year old, I actually follow pretty much all of your rules. I think most of them are just fashion don’ts in general! Plus, I feel like, as a teacher, I err on the modest side. I love to be fashionable and trendy, and I think that’s doable with all of the fun trends out there! I love your style and try to emulate it. I only hope I can age as gracefully as you! You look beautiful in both pictures, though – you really do!!
    Hope you have a great weekend!
    “The Busy Brunette”
    http://thebusybrunette.blogspot.com/

  63. Hi Cyndi.

    You look younger and more fashionable in your 2015 picture! Wow! 🙂

    I do break one of your rules though. I have Miss Me jeans with rhinestones on the back pocket. I wear them if I’m going out, usually with some type of dressier black top and heels of some sort. Not ready to give up those jeans, unless I get to big for them some day. 🙂

    As for flip flops, I only wear them casually. I have a pair of Haviannas that I love. I do want a pair of Tory Burch flip flops. I think it changes things totally when a designer’s name is on it! LOL

    Hope you have a great holiday weekend. Thanks for sharing.

    1. Gina, I also can’t part with Miss Me jeans!! We have spirit day on Fridays…and during football season, I think the blingier the better:-)… Just maybe, it is a Texas thing!!!

    2. I also like a bit of bling on the back pockets. Since I get compliments on them I believe I will continue to wear them.

  64. No short shorts, excessive cleavage showing, tight fitting clothes or ripped jeans would be on my list on don’ts. I don’t care for the camo look either. I think keeping an up to date haircut helps us as we age too.If you wear your hair super short , try to keep it fashionable. I see too many women my age with short hair cuts that age them.

    1. I agree! I cannot understand the attraction for the “cammo” look. And distressed jeans? Why would you want to wear something that looks so shabby?

    2. I am well over 40, but I do love the distressed jeans and the camo look. For me, it is all in how you style these items. Cyndi does a great job.

  65. I love your blog. You are so hard on yourself in comparing the pictures. You are beautiful in both.

  66. I personally believe there is a difference between flip flops and thong sandals, flip flops being the rubber shoes you wear in the shower. You can wear a cute backless thong sandal and most people call them flip flops. But the rubber ones are what we shouldn’t be wearing unless we are at the pool or public shower. Don’t you agree?

  67. I enjoyed your posting….It was a hard realization to give up my message t-shirts:) As for pantyhose, it
    depends on my mood; if they are good enough for Kate Middleton, then they are good enough for me:D As a 53 y.o. grandma, it does make me sad to be in the store and see mothers who are wearing the same low cut, distressed jeans and cut off tops as their daughter:(((

  68. I too have struggled with fashion as I’m approaching 53. I feel that ‘age appropriate’ must also factor in with ‘what I like’. I have been trying to be healthier with eating habitats and exercise as well. I’ve lost 30 lbs. And have had to replace most of my clothes. I find that what is trending is not always for me. My two mid-twenty year old daughters are good sounding boards. Your perspective is a great help.

  69. Love your blog, Cyndi! Thanks for these tips. I still go a little darker on my lipstick some days around the house; does anyone feel the current nude lipsticks really cannot be seen? I really have issue with fake Barbie doll pink lipsticks, too. Sometimes it is about wearing what we feel good in and not just jumping on every trend that comes around….

    Sorry, but I have issue with the ripped jeans fad. Seriously, I work hard to keep my guys in good looking jeans and then we go out as a family and see professional beautiful women in ripped jeans. I just do.not.get.it!

    Have a great holiday weekend; don’t take me or anyone too seriously. We are all having a tough time behind the scenes and we need to make each other smile!

    Julie

  70. I so enjoy your blog Cyndi. That list made me laugh out loud 🙂
    I think you looked good in your old photo and good in your current one! Nothing to cringe about here…
    have a great weekend

  71. Cyndi, please tell me what’s wrong with the 2012 picture – it looks like something I would wear!

    1. Jenny I don’t like the pants. They’re too wide at the bottom and they hit at an awkward place.
      They’re also a little baggy.
      Cyndi

    1. I use stress away from Young Living. I’ve mixed it with some coconut oil and use it as a rub. I put it on my neck and temples and shoulders to relieve stress and headaches. You could put it in a roller bottle and dab it on your temples or neck when you feel stressed. It smells great and isn’t a heavy scent. Even just breathing it in might help! Stress Away has really worked for me!

        1. Yes, they do still have peace and calming. I have tried that but don’t like it as well. It has a much heavier scent that is too strong for me.

          1. I’ve found a few essential oil recipes on pinterest to help with allergies. I haven’t tried them though.

            I did discover this winter that lemongrass oil wipes out sinus infection. I just combined the oil with coconut oil and rubbed it across my forehead and cheekbones (where ever I had sinus pain). Immediately I felt it working to relieve the sinus pressure. I applied it often and kept myself from getting a full-fledged sinus infection requiring antibiotics. Hip hip hooray!! So maybe this would help with allergies, as well.

          2. Thanks for that info, Jennifer–good to know! I found that sometimes the oil that I had the strongest negative reaction to was the one I really needed.

  72. I would love for you to post a more in depth and detailed daily/weekly routine for your diet and exercise. You look amazing and what a great blog you have. Thank you!

  73. You are not getting older, you are getting better! Appreciate all your tips and real life examples of fashion over 40!

  74. Cyndi, You def look younger now so way to go! I hope I can do likewise. Did you notice you have 11 rules? Two number 2s LOL I agree with all your points. Have a super holiday weekend!

  75. I’m actually 33, but love following your blog because I think you embody a great balance of (fantastic) fashion and modesty and you seem to have a beautiful spirit, as well. As a mom of three boys aged 1-9 it’s important for me to be someone who they can be proud of (even if they don’t know it) and to not embarrass them by over or under dressing or dressing inappropriately for my age.

    I hate matchy-matchy, as well, but I do like to look put together. I found your blog via Pinterest awhile back. Thanks for the inspirational ideas and conversations.

  76. Cyndi you do look younger now and love your list! I haven’t worn panty hose in 15 years or more. I never liked them and when the bare leg trend started I was thrilled! It does help that I have olive skin. I don’t wear shorts anymore at 58 but I do love a midi dress. They are hard to find that are age appropriate but J.Jill usually has some that are really cute. I have found that going a tad lighter on hair color is much better as we age also. Have a great weekend friend!

  77. I agree with your list too Cyndi. And yes, it would be cute to see you in the “do not wear outfits” he-he… thx for keeping us “in the know”. I would miss a lot if it wasn’t for you 😉 Enjoy your weekend and lets remember what it’s really about…all those who have served and gave their lives for our freedom!! Praising God for these brave soldiers! God bless you 🙂

  78. I agree with your “what not to wear” points! At 57, and a “Meemsy” for the first time in 2014 to Rowan & Cal – best cousins – my daughters made it loud and clear that I could NEVER look like a “farty-old grandma!” (excuse their language!). I, too, have been on a health journey, losing 35 lbs so far, and I love following your blog. Fashion never was “fun” for me before, although, I tried to dress fashionably on the outside at any weight, my “heart” never was having fun. God has/is healing broken places, and I’m realizing anew His amazing love for me…no matter what! My life verse is Psalm 27:13 – I would lose hope if I didn’t believe that I will see the goodness of the Lord in the land where I live! (paraphrased) His nearness is for me my good, and I see Him everywhere…even in the beauty of fashion! Happy day!

  79. I think the most important things are to dress in styles that flatter your body type and wear colors that are complimentary to your skin tone. When I do those two things, I almost always get compliments.

    And I don’t care how old you are – I don’t think anyone should be wearing mini skirts!!!! 🙂 I am appalled by the length (or lack thereof) of skirts and shorts these days.

  80. I’ve followed your blog for quite awhile and think you look great a few years ago & today! It is clear you are slimmer today though…just curious if you tracked how many lbs you actually lost through the changes you made?? Bravo to you!

  81. This list is perfect. I will say I wear spank hose in the winter as I’m uncomfortable with how my legs look. LI’m 51 though and had 6 children. Love tights too. The Holiday sweaters made me laugh – so true.

  82. I love your grey striped top! I found a tank recently in that grey stripe with the orange stitched design but it was too young because the back was too skimpy. I wish I knew where I could find one like yours! Any help with a link?

  83. Your list is great! I’d have to say that several things are your list apply to any age–but they may be more tolerable at a much older age (it’s ok if Granny wears a Christmas sweater with bells). I was a little shocked when I read “black hair color” (I have natural black hair) until I realized you meant dyed hair–then I totally agree older women with black dyed hair look goofy. Hopefully as I age people will be able to tell that my color is natural and I won’t look goofy!

    I also think it would be fun if you modeled some don’t—just for giggles!! And I also agree that you look younger now. And I love that top in the 2015 picture–can I have it when you’re done with it? 🙂

  84. Of course I have seen older ladies in their matching pant suits and look very distinguished in them… The ladies of London, England love their matchy-matchy dress suits and pants suits… The queen of England dresses divine and I always love the princess’s styles too! I think the dress of an older lady depends on the lifestyle of that lady, whether it is outdoorsy, active, or refine and dainty. I always have a little of both in my closet. The ripped jeans can stay with my daughter though….. Of course I am still in my 40’s and will probably have to dress a little older … soon… LOL maybe. 🙂
    I dress how I feel for the day!

  85. I totally agree with your list! I do have one question though. There are so really cute elastic waist shorts with a tie waist on the Loft site right now. I have been thinking about getting a pair for summer vacation but I don’t want to look like an old lady;) Is it ever appropriate to wear elastic waist items? And yes to the short shorts! I don’t even like them on my long, tall teen daughter – we have words about them frequently 😉 Susan

    1. Susan, I bought those shorts from Loft you are speaking of. I wore them for the first time the other day and my husband hated them. He never, ever says anything negative but he chimed in about those. Darn!

    2. The shorts that you’re describing
      at Loft have a paper bag waist. They’re not the frumpy short that
      Cyndi was referencing.

  86. The term “over 40” should not be taken as a blanket statement. While I think your fashion is totally age appropriate for you, some items will not be for me at age 66 (how did that happen?). I’m not necessarily lovin’ that knees get more wrinkly and upper arms wiggle more. Ugh. But, I am determined to be fashionable for my age. That means I dont wear sleeveless but rather a cute 3/4 sleeve. I also like a longer hemline in tops, if possible, and I’m comfortable and fashionable in peasant type tops and flowie fabrics. Button down shirts are always a classic too. I wear slim capris or longer leg shorts or even jeans cuffed up for summer. I like dresses to hit just below the knee along with a fun flat or sensible heel. The longer dress means I can avoid panty hose too. Shoes, well shoes, are my nemesis! What I want and what is best for comfort and stability are often not the same. I work on this one!
    Keeping a hair style current, jewelry, bag, makeup and a good attitude all help me to keep my appearance age appropriate without being dowdy (hopefully)! To summarize, be of cheerful countenance, don’t show skin that should not be shown, edit your wardrobe to your age and remember….you’re somebodys grandma!

    1. Sarah, i am also 66 and i just loved every single word you wrote. And, yes, i don’t know how this aging thing happened!!! LOL

      1. Maybe there should be a fashion blog for women over 60! Big gap between 40 yrs. and 60 yrs of age. Does anyone know of such a blog?

  87. No short shorts, please! (I really don’t like them on anybody, but especially women over 40!)

  88. Hi Cyndi,
    Much going on around here in south east KY. with home schooling, graduation coming up, and traveling to Ohio, Indiana, Tenn, Chicago etc….. so I will be backing up and getting all your blogs, when I can, I don’t like to miss reading one of them…
    Love this one on style and clothes, best for our age… I agree with all your 10 points the most. But those of us with a little Indian in us may already have black hair, and not need a color hee hee… Mine is originally very dark brown, almost black at the roots. but I do keep a color on it and a little lighter in summer then winter for those pesty grays. 🙂
    I love your style today as well as those of your, years ago. I do wear fip-flops, but not with a dress, I agree. Thank you for all the helpful tips.
    We went to Berlin, Ohio last weekend and enjoyed a little more simple life. It was great! Berlin and surrounding counties are the largest Amish Community in the world. It is worth a trip and reminds me of Gatlinburg – Pigeon Forge, Tenn.!! God is good – ALL the time.
    Have a blessed week!!

  89. This was a great post – Thank you!!!
    P.S. I also think you look so much younger in the 2015 picture than in the 2012 picture!

  90. Love your “don’t” list – I am 55 and laugh when I read that I shouldn’t wear high heels, cropped pants or distressed jeans. Love your blog and just received my first stitch fix. Keeping my distressed jeans!!

  91. I think it would be fun for you to show us examples of what not to wear – maybe using you as the model. Usually a good visual can drive home the message! 😉

  92. Cyndi, I think you look younger in 2015 than you did in 2012! It’s amazing how a few extra pounds can age us.

  93. I read an article not to long ago that said women over 40 shouldn’t wear t-shirts with a message. I have the cutest little shirt that says “Life is short, wear cute shoes” and I just can’t give it up……so I’ll wear it around the house because it makes me smile. 🙂

    1. I just bought one that says “Old is the new black.” Love it, and won’t give it up for quite some time, but on the other hand I wouldn’t wear it to work. I agree with Cyndi’s fashion rules in general as guidelines, but each of us needs to consider them in the context of our own daily lives. I’m about to become a grandmother for the first time, and find myself shopping for “grandma” clothes, which are totally not me. But I still feel like I need a few wash and wear, soft, comfy outfits to wear while taking care of the baby. I have an office job, so most of my clothes are very tailored and dry clean only. My daughter’s house is freezing all the time, so I’m on the hunt for some cute track suits or something with a soft jacket that will be suitable for baby rocking. Suggestions welcome from all the experienced grandmothers on this site!

      1. TexasAggieMom, is there a reason you are buying new clothes for baby loving (if I read your post correctly) vs wearing something comfortable that you possibly already have like boyfriend jeans and a tee? You could throw on a cardigan if you’re cool. I only ask because I try to wear my clothes for more than one reason except for gym clothes and swimsuits.

        1. I have 5 grandchildren & the youngest is 9. Never bought New clothes- just made sure they were washable.

          1. The best thing you can wear for your grandchildren is a loving heart with a great, playful sense of humor! A new wardrobe is not essential but stay away from the Grandma Department and shop for that baby! I LOVE, LOVE, LOVE being a Gramma yet I’m determined to keep myself healthy, looking youthful and as on trend as possible for my husband, myself and my family, including my grandbabies. Have fun with your first grandbaby…your life will never be the same!!