Over The Knee Boots For Women Over 40

Over The Knee Boots For Women Over 40

This fall season seems to be extreme with the boots. The two popular styles are booties (which are ankle boots) or over the knee boots.

Now I know some of you reading this are going to immediately say “no” to the over the knee boots. But I think women over 40 can pull this look off if it’s worn the right way.

Here are some over the knee boot styles that I like:

I know this girl is young in the picture but I think this would look go on older women too.

Over The Knee Boots For Women Over 40
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Chunky sweaters, skirts and boots are popular for fall.

Over The Knee Boots For Women Over 40
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These next three outfits have tall boots with a touch of leopard print.

Over The Knee Boots For Women Over 40
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brown boots with purse
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brown bag and boots

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So what do you think? Will you be wearing over the knee boots this fall?

Beauty For the Heart~~

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Have a blessed day!

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  1. I am 52 and I just LOVE my over the knee boots, I have 2 pairs! I am 5’7” which may make the difference, but I think it is WAY more about attitude and personal style than anything else. I want to get more adventurous as I get older and be true to my own style, as long as it’s kept classy (as in Advanced Style) – style(and beauty) is an attitude thing not an age thing anyway.

  2. I will be 64 this week and had to have these boot. I found a pair for $40 at Marshalls and wear them with denim leggings. Love them with black and get a lot of compliments. I am 5’4 and about 150 lbs but people always think I am 120 lbs. I am a mental health counselor so I like to be somewhat conservative in my dress. As my mother said, style will kill me and I cant think of a better way to go.

    1. I’m with you. I just turned 50. After viewing a much older woman wearing a pair of red suede over the knee boots on the Advanced Style blog last week, I refuse to give up my OTKs. I love that blog.

  3. I am 47 and 5’8″ I bought these boots and they look great! with the right top they look really classy and fun! its all about attitude ! I love your posts keep up the good work orla dublin ireland

  4. I’m over 40 – but just barely! I’m nervous as all get out about these OTB because I just ordered a pair online. I’m very tall and I know they are only slightly taller than my calf height boots. I’m hoping I don’t look a fool in them as the deal I got was incredible!

  5. I agree with all the short ladies above, leave the over the knee boots to the younger, leggier girls!! I have never owned a pair because of my very short legs. Regular boots are over my knees now!! Love the ankle boots!! Thank you for your wonderful posts!! 🙂

  6. I’m dying over here! i thought not more than ten minutes before reading your post, “I need to get a pair of over-the-knee boots.” I guess great minds think a like, but still!
    I especially like the style in last pic and the one with the skirt. I din’t see Pretty Woman and am saddened by the name these boots are now called because of it. I’m thinking more Clute, and she looked great.

    I agree they’re more for longer or at least slimmer legs, but can look really cute. I remember the trend from A LONG TIME AGO and have been waiting for it to come back in so I could finally wear it.
    Thanks for the post.
    P.S. They’re only tall in the front.

  7. I just don’t think it works for us “older” gals. Some fashions are just left better with the twenty something and below group. I also agree they have a “Pretty Woman” feel and that was before her classy transformation….

    1. I agree for thigh-highs, but over-the-knee is very stylish and definitely works for older women. I have a pair, am 62, am people think they look good. I wear them with dresses that come just above them. I’m 5’4″.

  8. They remind me too much of one of my favorite movies!!! Julia Roberts as the hooker in Pretty Woman…so I will stick to booties and tall boots:D

  9. I’m almost 57 and I too think this look is better suited for younger, tall, slim girls. I’m 5’3″ and couldn’t pull it off, not that I would try. They look too uncomfortable and confining. Like the pointy toe heels so many women wear – yuk yuk yuk! (Sorry I digress). Of all the pictures posted above, the only one I like is the pic where the boots are paired with the leopard scarf. Love that look!! But the boots on the “source” page don’t look the same. I do like those tho. I’ll stick with my booties and calf height.

    1. I have seen some pictures (and on TV) of older women with the chunky calf-high booties and they look very matronly and always make their calves look fatter. I think the OTK is much more flattering and elegant, and no matter your height, you can find a boot that comes right where you want it.

  10. I too, don’t think this trend is as much about age as body style. Some of the ladies here say they are short and can still rock them … I however at 5’2″ am very curvy and have big thighs and hips! I’m afraid the OTK boots would make me look like my legs have muffin tops! Ha ha! Simply love them on those with long thin legs however:) Thanks Cyndi! Krista

  11. Last year, I found the most gorgeous pair of black Steve Madden OTK boots at Goodwill, of all places, and wore the besnizzle out of them all winter. I’m short, I’m 51 and yes, I call them hooker boots. I’m still looking for a brown pair.

  12. I so appreciate the work the you do to research and hunt for pictures – it is a huge help to people like me who can not figure out how to find “real” fashion….the stores sites are just pieces and the fashion news is not practical. This is a big help! I have to say, I feel like if I did wear them, they would bother me — they look like they would hit the back of the knee with every step =0)
    But….if a trend hangs around long enough, I am usual right there with everyone else….haha!

  13. I, too, am short (5’1″) and spent years in boutique sales. I do love over the knee boots, and had a pair of black suede. They were great! I wore them with black tights and a red sweater dress that hit just above the boot. I know that the boots don’t elongate the leg. I just decided at one point that I would wear things that broke some of the rules if I loved them. It was fun, and I always felt great.

  14. I love the look of these photos but I too am on the shorter side so they do not flatter me at all 🙁
    I can embrace the ankle boots though 🙂

  15. At 5’2, over the knee boots would cut me in two! I’ll be staying with my regular boots and adding a pair of booties to my wardrobe. A tall, slender girl can pull this off and look classy if her outfit is tasteful. For me personally, I would feel like I’m trying to dress like a teen/college-aged girl which is usually a big no-no.

  16. I’m with Cheryl and Bonnie because I have short legs but I love booties. I like the look of the over the knee boots on tall gals though.

  17. I wont be wearing over the knee boots. The weather here doesn’t get terribly cold for those type of boots. Looks like it would be uncomfortable to sit with your legs crossed. I will be wearing ankle boots though.

  18. well, I should not really break my rule about not saying negative things but some of the under 40s I know are calling these things hooker boots. perhaps it is because our weather really does not lend itself to making such financial investments aka cost per use. hope it is good for some chuckles.

    1. we have cold weather and wear boots here, and the younger set calls them the same thing ( I was wondering if I should say something, so I am glad you did!)

  19. They look a little clunky to me, and best saved for the tall and skinny types. I do plan to embrace the bootie trend though!

  20. Love the looks, but as a vertically challenged person, I think these might come up to my hoo-ha! That being said, boots can really be an investment, my jury is out on the bootie trend and the tall boot trend is an I don’t think so. I kind of love the calf to knee high boot. I do totally agree with you that a 40 something can wear this look. As always, love the beauty for the heart!

  21. Alas, no; with my short legs they wouldn’t look right and would only accentuate the shortness of my legs. But I am glad to see flat boots in style.