5 Tips for Wearing Shorts Over 40

Hi ladies! This time of year, I get asked about shorts for women over 40. How to wear them? What length? Today, I’ve got 5 tips for wearing shorts over 40.

First, let me say if you don’t want to wear shorts, don’t wear them, there are no rules that say you have to wear them.

There are other options; dresses like this one from LOFT are a great casual and comfortable option.

Tee Dress (TTS)// Sneakers (TTS)//Earrings

This dress from Amazon can be worn with flat sandals for a more casual look.

Short-Sleeve Dress (I’m wearing a small, TTS)/Heeled Sandal

Maxi dresses are on-trend and a great option for spring and summer.

Maxi Dress (I’m wearing an XS)//Earrings//Sandals (size up 1/2 size)//Necklace 

I love jumpsuits, and this one from Gibson is really comfortable.

Black Jumpsuit (I’m wearing a small, CYNDI15 for 15% off)//Sandals (size up 1/2 size)//Earrings//Necklace

Here are 5 Tips for Wearing Shorts

Crewneck T-Shirt (I’m wearing a small)//Rolled Denim Boyfriend Shorts (I’m wearing a size 27)//Calla Slide Sandal (TTS, pink light color)//Earrings

1. Wear self-tanner. Self-tanner hides imperfections, and I always feel better when my legs aren’t so pale. I recently shared some of the best self-tanners in this post HERE.

2. Find shorts that fit you well. Don’t wear shorts that are too tight or too baggy. I recommend sizing up in your shorts from your regular size, so they aren’t too tight.

UNIONBAY Women’s Darcy Stretch 5″ Inseam Short (I’m wearing a size 7)//Embroidered Puff Sleeve Sweatshirt Tee (I’m wearing a small)//Earrings//Sandals (size up 1/2 size)

3. Inseam is always a big issue for most women who are over 40. There’s no hard-fast rule, and it depends on your height and body type as to what length will look best on you. Typically shorts are short (3½” – 4″ inseam), mid-length (5″-7″) or Bermuda (9″-11″).

I’m 5’5″ and prefer a 5-inch inseam.

4. Pay attention to the leg opening. I don’t like the leg opening too tight because it accentuates the largest part of my leg.

Eyelet Top (I’m wearing a small)//Denim Shorts (I’m wearing a size 28)//Earrings//Sandals (similar option here)

5. Think about your body type, accentuate the positive, and minimize the problem areas. 

Eyelet Top (I’m wearing a small)//Black Shorts (I’m wearing a size 6)//Sandals//Earrings

  • Tall ladies typically look great in bermuda shorts.
  • Short ladies with shorts legs should stay away from bermuda shorts.
  • If you’re curvy, high-waisted shorts are your friend. They accentuate your waistline.
  • If you have a boyish figure (straight up and down figure), you can add details to your shorts—cute pockets on the backside with detail.
  • Apple shape ladies typically have good legs, so accentuate the positive with dark wash jeans with a cuff.

Bonus tip: To create longer legs, always wear a light-colored sandal with your shorts.

Rolled Denim Boyfriend Shorts (I’m wearing a size 27, these run big, so size down)//Slide Sandal (size up 1/2 size)//Eyelet Trim Top (I’m wearing an XS, TTS for Gibson, CYNDI15 FOR 15% off)//Earrings 

Do you have any tips to share?

Thank you for taking the time out of your day to stop by my blog. I’m also on FacebookPinterest, and Instagram.

Beauty for the Heart~~Hope deferred makes the heart sick, but a longing fulfilled is a tree of life. Proverbs‬ ‭13:12‬ ‭NIV‬‬

Our whole globe is suffering from hope deferred. It’s been 14 months of a health threat, social unrest, and fear. We’re all longing for “normal,” and it is continually deferred.

But the Lord is to be our only hope, our ever-present! He is never deferred. We have access to Him 24/7, and his presence is not limited by any circumstance or atmosphere of unrest. He is our tree of life! -Kristin Knipp

Let your beauty shine from the inside out today!




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  1. Love these suggestions! I absolutely love your style…..I plan to mimic some of these ideas! Thank you~ <3

  2. You look great in every single thing!
    Love your tips about shorts.
    Shorts are a challenge when you’re (way) over 40, but I agree about the inseam being important as well as not to tight on the leg. I like a 9 to 11″ inseam, being 5’2″. But I don’t wear shorts as much as I used to. Pedal pushers are a good option. I love the dress option too. They keep you cool while still looking good! Love all the dresses you showed.

  3. I am full figured and apple shaped and I agree with your comment about those of my shape typically having more slender legs. It does sometimes make it difficult to find shorts that are not HUGE in the leg area though. Plus size clothes designers seem to think that all chubby ladies carry weight in the hip and thigh area. Since I do not, shorts that fit my middle tend to be way too big in the legs and look very matronly. Any suggestions?

  4. Thank you for the verse in the BFTH. I’m struggling with the when you get out more and meet up with friends. It’s been all our kids and grandkids and now they are meeting with friends and so our circle has gotten bigger through them and we don’t get the social. Mentally it’s been hard on me. I’ve met up a few times with a girl friend and it refreshed me. We aren’t meant to do life alone. It has been hope deferred for me too long. Thanks for shorts tips. I’m one who prefers casual dresses or skirts. I just can’t get the right fit on shorts.

  5. I’m 5’3 and seem to gravitate towards the 4”-5”length if possible. I noticed you didn’t include white shorts… Any reason ? And will you be styling some? I have white cotton shorts but would like to get a nice white denim pair. I’m a fan of cute summer dresses but I must say I love wearing shorts too! I also would like to see some graphic tees for a post. Stay safe with all the storms down that way. We are finally back to sunny skies and warm temperatures this week so outdoors to read by the pool is on my list🌷

  6. Happy Tuesday, Cyndi!
    I really enjoy your blog and often make purchases for myself and family members. Thank you for all the fashion help! We have so much in common: height, sizes, love of family, and of Christ. Also we are both former pastor’s wives. 🙂 Thank you also for being so intentional with your faith and for spreading sunshine.
    As for shorts, I love Belk’s Caroline shorts by Crown and Ivy. Mine have a 5′ inseam. They were having a sale this weekend. Also, have had success with Loft shorts. Hope this is helpful! Blessings!

  7. Hi Cyndi,
    I have been following your blog for years, but it has been especially helpful having your blog through this pandemic. Thank you for being a bright spot. Could you give some more short recommendations? I’m similar size to you and they were out of the olive pair you recommended. I would also like to find a denim pair.

    Take care,

  8. Hi Cyndi,
    You always look adorable! I just started getting your emails and want to say you give great advise!

      1. The blue maxi dress from Old Navy is already sold out in every size. Bummer, that is sooo cute. Hoping Old Navy will restock soon! Loved the outfit Cyndi. Thank you, you’re a doll☺️

  9. The Classic Solid Maxi black dress from Chicos – does this dress have a zipper and does it feel heavy for summer evening wear? Waiting for your response. Love your fashion.

      1. Thank you for being the sweet lady you are. When I read your blog at the end you talked about God, I needed to hear those words at that moment. Thank you so much, Laurie

  10. Hi Cindi,
    Thanks for including some shorts in your post today, I will have to give those JC Penny shorts a try. I also love the Loft Rivera shorts with the 5 inch inseam. I am 5 ft 5in and feel the 7 inch inseam is to long for my height.
    I loved your beauty for the heart that quote was so spot on for me today.

    Shannon 🙂

    1. I find wearing a small healed sandal gives my legs a little longer look. I love the nude colored sandals!

  11. Great tips Cyndi. Thank you. Love the Ravi quote. What a blessing that man was to so many! 💗

  12. I was just thinking of a post on graphic tees too and saw many have mentioned it. Could you do that? You always find such cute sayings. I love a good graphic tee. You look great in shorts. I wish I was more confident in my legs and the shape they are in. I know sunless tanner would help but with all the chemicals in them, I have stopped using them. I would like to try the first one you recommended but its unavailable it says. Do you know anywhere else to order it from?

  13. Love that you quoted Dr. Zacharias today. Bless you for that sweet tribute to such a wonderful servant of God.

  14. Great options. I like to mix it up a bit! A post on some cute tees graphic etc to wear with shorts would be great.. love all your suggestions:)
    Great BFTH ❤️

    1. I was so impressed how you talked about other options like dresses, skirts etc..how clever is that. I love all the ideas you talked about and I ware them.

      I’m 5’4 are light color shoes the best cause I seem to feel like I don’t look as short. What do you think.

      You were so right about the capries being above the knee. I’m sure its because of my height Thank you for your advice it’s very good.

  15. Hey Cyndi,
    I’m looking for some cute Summer tees with words on them. Can you recommend some places to find some?