OTK Boots Over 40 Go Mainstream on Instagram

It’s interesting to see a fashion trend evolve. A few years ago, I blogged about Michele Obama’s over-the-knee boots. At that time, many of you wondered if they were “age-appropriate” and whether they were too edgy for her to wear to church.

photo credit: Huffington Post


How things have changed! The age-appropriate notion is quickly fading, and over-the-knee boots have become much more mainstream, with 40+ bloggers wearing them routinely on Instagram. Here’s a look at some cool ways to style this popular style of boots.



Keep it classic, and you can’t go wrong with over-the-knee boots. Black leather boots worn with a black top and leggings create a long, lean silhouette. This gorgeous gray scarf adds a dash of sophistication.



California girl, Catherine,  looks West Coast cool in these sexy over-the-knee boots that are buttery soft.



A chunky, knit pair of jeans and rustic over-the-knee boots. Shannon has put together a great fall weekend look.



Erin shows us how to channel your inner boho girl by pairing over-the-knee boots in delicious plum with a beautiful bell sleeve top. This outfit is a cool nod to the ’70s.



Mia shows us that faux fur is another great thing to wear with over-the-knee boots.



Pamela proves you are never too old to flash a little leg. She’s got the right proportions down pat.



Suede is one of the most popular types of over-the-knee booties, and these moss green ones Yvonne has are divine. These are a great way to add a little color to your outfit.



Kelley looks pretty and perky in a cute military-inspired look that combines an officer’s jacket with buckle over-the-knee boots and a flannel hat.



Heather’s black suede over-the-knee boots are so thin and light, they almost look like gloves. That’s what makes them so sexy!



Jeannie shows us how over-the-knee boots can give a casual dress a  “wow”  effect.



Here’s Jamie sporting some of the most original over-the-knee boots I’ve seen. These are fabulous Southwest fashion statements.



I love the color of these stunning over-the-knee boots that are a smokey gray with a hint of plum. See how they transition white jeans into a rich fall look?

Do you wear over-the-knee boots? How do you wear them? Here are some more fabulous ways to style over-the-knee boots.

I’m always on the lookout for Stylish women to feature. Be sure to add the #fabulousafter40  HASHTAG to your Instagram posts so I can find you easily!

Join the Conversation

66 thoughts on “OTK Boots Over 40 Go Mainstream on Instagram

  1. I love over the knee boots and I wear them every where with every thing but mostly with tights or thigh high socks.they were beautiful.thank a million!

  2. I love the gray boots with the white jeans. It looks classy. My problem with OTK boots is the same as with all other. I have very muscular calves from years of weight training so the shank doesn’t ever fit. I’ve tried purchasing wide calf styles but they just aren’t enough. It is a shame because I think the OTK boots would be great for making my legs looks longer and hiding their muscular shape.

  3. How timely is this? I just posted two over the knee boots on Instagram. I love your content. I am so happy to have come across your site. I just turned 49 and the biggest issue I have come across is finding clothing that is not geared towards women in their 20’s. The dresses are way to short and most sites images are of young women. I just can’t relate. I created an online shopping destination for women our age. It is my goal to have the site filled with images of women 40 and over as my business grows and our budget allows for it. There are so many beautiful women our age (inside and out) that need to be celebrated.

  4. I’m only 5’2″ and I’m an apple shape and I have yet to try this style. From what I’ve seen you can’t have too thick of thighs to wear them. Already with my wide calves boots are hard to find I can’t imagine trying to fit thighs too! I do see one way to style them that would work though and it would be with a skirt or dress like Michelle Obama where you don’t see the thigh above the boot. Then it almost looks like you’re wearing leather/microfiber leggings. I might give that option a try. Thanks!


  5. Hi, I’ just turned 54 and I just bought the suede over the knee boots from Cole Haan. And I must say I love it and didn’t look like I’m trying hard to be young. It’s all about balancing it with the rest of your outfit. I wear them with jeans. I wear them with dresses that are not too short and not body hugging. And I have a dress that’s a little shorter (but not mini), and I wore lighter black tights, so I’m still showing some skin but still covered.

    To all my fellow 50 plus fashionistas, our age should not stop us from wearing what we like. Our goal should not be to look like we are still in our 20s or 30s but to be fashionable at our age. For me, I stay away from cheap-looking fabrics and stop shopping at forever 21 (that’s where my 16-year-old shops). At our age, our goal has to be classy and fashionable. Cheers to us from a proud 54-year-old!!!

  6. Yes, I saw that photo of Michelle Obama and saved it to my style ideas folder. What a fashion icon she is – even more so than Jacki Kennedy, who was also ahead of her time. It hardly gets cold enough where I live in Australia, but I still love the look of a stylish pair of over the knee boots. Of course, you want it to be more First Lady than Pretty Woman…

    1. I’m 51,-athletic and have great legs and just bought two pairs of these !
      I would have wanted to sear a shorter dress but now that I’ve read this i will go for the longer dress that meets the top of the boot !!!!

    1. I think that long leather thighboots look great on small women. And leather thighboots look lovely with long cowl neck jumpers.

  7. Usually I love Michelle Obama’s fashion sense – but I don’t care for this look at all. She can wear over the knee boots no problem, but combined with cleavage? It’s a little too Brittany spears baby-baby schoolgirl. I think a thick turtleneck cable knit sweater would have worked better. Her daughter looks more like a first lady in this photo.

  8. Hi…a little late for comments but being that over-the-knee boots are hot again this season I was busy reading all the comments. I agree it is difficult to keep with “age appropriate” styles but what do we define as age appropriate as one person mentioned even a 20 year old can look inappropriate in the wrong boot/outfit. I’m 50 years old, 5’7″ tall, athletic and slim (I try to take care of myself). I finally reached a point in life where I actually wear what I have always wanted to but was too shy to. I am searching for the perfect over-the-knee matte black boot (simple style), long vest, nice dark jeans or perfect dress and hope to pull it off. I sometimes judge my clothes by comments (or lack of) that I receive. Thank you to everyone for sharing.

    1. Yes, Kelly, I’m only just starting to wear some of the clothes I’d been too shy to wear when I was young also. I’m 56, and 5’10” – not quite as slim as I was when young, but not too podgy. I’ve been looking at the Stuart Weitzman over the knee boots, though I may have trouble getting them in Australia. But I like to dream… I hope you find the ones you’re searching for…

  9. I think they look great as long as they are not those double platform hooker boots or those like the ones Julia Roberts wore in Pretty Woman. Recently I’ve seen Sharon Stone, Madonna and Carine Roitfeld. They are all in their 50s and they looked great.

  10. A boot’s shaft naturally slouches and loses its shape through normal wear. Try a pair of Elevates which prevents boot slouch with the use of a thin leg strap and magnets. It’s pretty cool! Check it out at iheartelevates.com. Good luck!

  11. I personally hate the term, age appropriate. I think you should wear whatever makes you feel sexy whether you’re 23 or 63. I’m 23 in case anybody’s wondering. My mom is only 45 and she always feels she has to wear ‘age appropriate’ outfits and she’s miserable in them and spending hard earned money on them. So, in my opinion, if you feel comfortable wearing these boots then wear them. Don’t let society pick your wardrobe. Age is just a number.

  12. I think it’s all in your persona. I wore thigh-high boots in NYC back in ’86 & ’87 when nobody wore them. I can’t recall anyone of my friends or anyone at any of the fashionable NYC clubs wearing thigh-high boots back then, except for me. Well, a lot has changed since then, but even at 44 I still am going to wear my brand new BEBE over-the-knee, suede lace-up boots. I don’t look 44 and I’ve always liked thigh-high boots. I’m not overweight, and my husband loves them! So there you go! It’s a personal choice that has to be part of your personality. Of course, I feel I would only wear them with certain outfits. Obviously, at my age I wouldn’t feel right wearing the shiny one’s like I did back in the’80s,, but we are still women, and we should enjoy what we wear. My husband loves it, and that’s all that matters!

    1. I am in my 70’s and have worn thigh high boots and crotch high boots for over 45 years I have over 30 pairs of boots from calf high to crotch high my husband adores me in leather be it skirts,slacks,, coat, jackets or my form fitting leather jumpsuits. Over the years I have received many wonderful comments. The most common comment from other women is; “I wish I could wear leather like you” I am no different from any other girl, but I love how leather has kept my husbands attention and has opened the door to meeting many wonderful people.

  13. I am 46 and think it is fine as long as the heel is low and the boot is not shiny and it is paired with a long sweater/ leggings or sweater dress and opaque tights…I am 5’9″ and thin so this may work for me a little easier…

  14. Well I’ve just bought my first pair of thigh high boots. Black suede & gorgeous. With opaque tights & a longish skirt they should look ok. Wow, people are certainly touchy over this issue. LOL I’m 5’10 so I think all will be well (here’s hoping).

    1. Hi Lucy,
      We think its great that you have gone for it! Our bet is that you are going to get lots of compliments and have a blast wearing them!
      Keep us posted. Deborah has a pair of black suede ones, too! Just saw an interview with Katie Couric a few months back where she had a pair on and thought she looked fantastic!

  15. I would just like to say, my mother is 52 and has 5 younger daughters that keep her in style. She manages to pull off new trends in a classy and age appropriate way, and I feel that a lot of women over 40 wanting to follow the trends, can, as long as you keep it age appropriate. I dont have an issue with older women wearing uggs, they are just like any other boots out there, and arent just for younger kids. I like to see older women that DO follow new trends because it seems like they really care about their image.

    1. Hi Heartly,
      Being up on trends makes you look modern. Being a slave to trends makes you look like a fashion victim. I think there are LOTS of different comfortable casual boots out there. I wouldn’t recommend Uggs because they are clunky and because with so many young kids wearing them they can look a little silly on mature women.

    1. Hi Lourdes,
      That is a good point…many women have complained that it is tricky to keep thigh high boots to stay up! So be forewarned if you are thinking of buying a pair…make sure to walk around the store a few times and see if they fit properly!

  16. I am a 45 year old woman and a mother of three. Just yesterday I wore my light shaded grey velvet thigh high boots, which I matched with my woolen violet dress that is a bit short and sexy. I wore a black wool coat with a fur cap and my hair was tidy and wore fair makeup. The dermatologist that was interviewing my daughter on her visit commented that I looked too young for a mother of an 18 year old. But I must say that I do a lot of exercise, walk a lot, prefer the stairs to the elevator, don’t eat junk food and don’t smoke. All of these things help a great deal.

  17. Hi Deborah, I have purchased a pair of the nine west suede boots around november (they are actually the ones pictured at the top of the page, but in black). I love them and have worn them so often, but they now fall to my knees and will not stay up! Please help.
    thank you thank you thank you!!!

  18. Have just been thinking about buying some thigh-highs for winter. It’s the middle of summer here (Australia) & I think I can just about get away with them with opaque tights & a ‘not short’ skirt. I’ll be 45 in May. Understand that nobody wants to look like a hooker or a try-hard but I think if the rest of the outfit is stylist as opposed to slutty it should be ok. Thanks so much I love this site.

    1. Hi Lucy,
      I have seen a lot of great examples of over 40 gals sporting thigh high boots and looking fab! Sounds like you got the idea and will pull it off!
      Go for it and have fun!!!

  19. I would LOVE to know the secret to gettting these boots to stay up. I have a pair of flat suede thigh-high boots that I love, but they slouch so much that they just look like slouchy knee-high boots. I’ve tried everything, methods thatiI am too embarrassed to share here (one even includes chopsticks and tape) and nothing has worked.

    1. Good luck with finding out “the secret”! One tip that I can share, is if you take your suede boots to a really good shoe guy, he can sew them up so that they fit, or put in some elastic at the top (just in the back) to help hold them up.

      Finding a boot that fits snugly around the leg is hard to do, especially if you have thin ones, however a good fitting boot is really a fashion must have!

  20. Boots are the sexiest item a woman can wear. I confident woman of any age can pull this look off, and you can bet there are many men who will appreciate her for showing her style and confidence. I have complimented many older women who have the confidence to wear sexy boots of all styles. keep your boots on…

  21. Please help me find a good pair of thighhigh boots for my wide width feet! I love these sort of boots. I’m 43 years of age,and would LOVE to own a pair. So if you have any suggestions on where I can find them to purchase, I would be very greatful for your help. Thank you kindly.

  22. Hi, I need some advice about this trend. I’m not really tall and i really like the look but im scared that it will shorten even more my legs.

    1. Hi Jennifer,
      Don’t be scared.. How tall are you? It can actually lengthen the look of your legs. The best advice I can give you, is go out and try them on, and wear the pants or skirt that you plan on wearing with them to the store… If you put the boots on and feel ridiculous, than you know your answer. However if you feel super wonderful, then go for it. Have fun!

  23. Hi

    I really like your articles. I’m in my late 20’s but do agree that these boots have to be worn with appropriate items depending on the age and size of the wearer to look elegant and may not suit everyone across the board.


  24. It’s how you wear it, look at Kris Jenner Kardashian she wears riding boots all the time and she looks gorgeous. I personally wear them with jeans or stretch pants, an oversized sweater and accessorize it with a fashionable pashmina scarf,wrap or shawl and I’m 53 and proud of it………. Even a 20 year old can look slutty if she dresses inappropriate.

  25. I just bought a pair of Stuart Weitzman hilos. They have a low heel. I’m 5’9″ and weigh 135. I wear a size 6. I am on the high side of 40. But these are so cool! I hate tights and my main reason to get them is it’s getting cold in Colorado and I love my skirts. I plan to wear them with my slightly above the knee dress skirts and try pencil skirts for work. I avoided the high heels to avoid a slutty look. But these are practical and sexy. I’m a little nervous to try them out but I’ve been jonesing for them for weeks. They were crazy expensive but hey, Madona, Heather Locklear, Demi Moore, they are all my age and I think they’d look great in them. Tell me if I’m wrong!

  26. Natural physical beauty is the actual debate. Many young women possess it. Many do not and never will. Many women are beautiful in their 50’s as they are the many who were in their 20’s. Thigh high boots….Wear them

  27. My wife and I are over 40 but we both look much younger. So we decided to buy the Gucci division thigh high boots. It was very hard to get them, but they look great. The only thing is, they don’t stay up. But the boots are worth every cent.

  28. OMG! I’m looking to order a pair of light gray suede thigh high boots and I end up here. How can so many people worry about their age?!? I’m about to turn 43 in days and OK, I guess I’m very lucky since I still have zero wrinkles and I get carded for cigarettes (I’ll post a pictures if there’s any doubt). But worrying about it?!? Hell no! I hope I never do! Looking sexy WITH CLASS is something all women of ANY age should worry about, however. (Maybe it’s because I’m French on that one?) And another thing: what is this thing about cutting your hair and looking matronely after 40 in the U.S.? Nothing wrong with VERY LONG slick hair in a nice high ponytail! I say forget the number, IT’S NOT EVEN WORTH ACKNOWLEDGING! Some people at 40 are the exact same as some others at 25 physically, and the same as some others at 50! What a trip society has put on women here. How sad! Free yourselves! ^_^

  29. Hey Deborah…..Do ya’ll have any pictures showing examples of how to wear the new boots? I’m 41 and 5’9” and would love to give it a shot….but not sure where to start!
    Thanks, Julie

    1. Hi Julie,
      Yes, I will take some soon.. until then, you are young and tall… a PERFECT combination!!!
      So how to start? I would start by looking though fashion magazines and online catalogs to see what styles you are drawn too. Then go out to the stores in a pair of TIGHT jeans and try some on. No need to buy right away… just see how you look and feel in them and think about where you will wear them.
      You will need to decide if you want them in leather or suede, with chunky heels vs a fine heel, low or high. (BTW…Suede tends to look more casual) You will find that you will quickly see what you like or dislike and if you even feel comfortable in them. This can be a fun process and will have you really feeling out of the box!
      Also, I love to see pictures too, so take your camera to the store and send your photos.Good luck!

    2. Hi Julie,
      WOW, 5’9 and only 41, you can pull these off no problem!!! Just start on where you want to wear them, so you can get the feel of heel style that you will wear the most and go out and try some of these puppies on! You could go with flats or a wedge or heel and you will look stunning. Send me a photo!

  30. Deborah is a mom with 3 small kids
    Yep I take your point and you are dead right about when do you wear such a high statement item. We live in a very small village of 50 houses where people walk to work at the local farms. We have a house in London and it is there, Paris, Amsterdam and NY that one can wear exiting cloths and be appreciated for it. We have 5 children all between 31 and 20 and the three girls all enjoy going out with their mother, probably because they can get into shops they would normally not get past the door man .
    It is Polly’s birthday on Sunday and I have booked Sunday lunch at Simpsons for us all and Polly is giving her new Nicholas Kirkwood (birthday prezy)spider Webb shoes a run, they are exquisite works of art, I love lunch at Simpsons but it is Polly in her shoes I want to watch. Then on to Old Bond St where I will be bankrupted as I know Polly has her eye on the Balmain tux, when she puts on great cloths I am sucker as it is me who wants her to have them as much as her.
    Are you able to help as far as posting a proper sized picture?

  31. Hello again
    The question itself “are thigh highs Ok after 40” makes me want to speak out.
    Take a look at Carmen Dell’Orefice, bit fierce but wow and it is not all plastic, at 78 she carries herself with confidence and dresses with grace and elegance.
    Very funny about the Ladies of the night, you may pretend to be prudes’, but I recon you know the answer.
    We were having diner outside a restaurant in Notting Hill last night and watching the world go by, some dressed up and some just taking the dog out, I said dog not husband.
    A group of girls about 8, say ranging between 22-30 came past and without exception they looked a mess of overdressed and or bad combinations which they should not have used with their individual body shapes ect. Polly is a designer with masters in art history, and I work in structural design, I used to model for catalogues some millennia ago and Polly was a house model in Paris so there is a bit of history we have collectively to call on.
    I think that if the group had been 40 plus then there is a 90% change they would have all got it right in terms of style appropriate to body shape.
    Oh just for the sake of interest look at Gucci.com/uk on line shop, the two styles of Division boot (we have the leather version, patent one is to busy, fussy) now look at Gucci.com/US and the same division boot. I am relieved that the UK was not sent the flat version, this is not new we have had the same problem with Prada, certain styles not been available in one country of other.
    Mark& Polly

  32. Hey Folks; I was thinking about when wild pair was open in Wisconsin and I bought my girlfriend three pairs of thigh high boots. All different colors of course. Anyways as a guy I was partial to thigh high boots and think they look best via jeans and a turtle neck via the fall. I went to Vegas and Had a pair of guys thigh highs made called General Custers. Yes made from scratch and lots of stitch. Sure and wore them biking and clubing. Got lots of looks and some guys made gay statements but I just kept on with the show. In fact in the clubs the gals would come over and ask where I had them made for conversation. I think being different is great and in Green Bay wearing them some Packer PLayers asked where I got them and thought about buying a pair or having them made. Or even buying a pair for there girlfriends and Mrs. Carry on because boots rule!!!!!!!!!!!!!!

  33. Basically the advice I hear is not to wear this boots unless you look younger than 40 and are thin. I’m an extremely youthful looking 45 and relatively thin (6/8) but I wouldn’t be caught dead in this trend.

    Unless you’re a performer or in fact, a hooker, I would pass on such boots 40 or 20. That’s just my opinion of course. They look slutty anyway you slice it.

  34. We are London based. My god, what a dull outlook, 40 and you are finished. Last year I my wife the bought the Gucci OTK with tassles, Etro thigh high lace up and others. Remember Devil Wears Prada? She has the boots. This year we have the Gucci Division Thigh high in leather. They arrived last week and Prada OTK ridding boot in black, the Balmain zip boot in leather and she looks awsome, elegant and sexy. A

    She would never go alone and she never dresses the boots in a way as to look overt, hell of a difference between sexy and overtly sexy. At 5’8″ and a 5″ heel, legs to die for and a figure to carry any clothes on the catwalk. All I can say is there is life “well” after 40. Elegant is the key, dress trash and you look trash.

  35. I had always wanted to try this, so last year I finally broke down and bought black microfiber over-the-knee boots. I wore them with a vintage black and red brocade New Look dress [fitted bodice, wide! skirt that ends at the knee]. The very tailored and modest dress with the boot took the costume look out of the vintage dress and made it modern. Oh, and I am 45.

    1. Would love to see a photo! …..That’s the trick with dressing over 40 ..taking the costume look out of something. Pair something a little more trendy with something classic and simple to look fashionable but classy.

  36. My Wife has just turned fifty although looks a lot younger, she remembers thigh boots the first time round. I would love her to wear thigh boots, although I think there best worn with a wrap round dress or a longish skirt with splits. We don’t really want to attract the wrong attitude we just want to have fun, she wearing them and me getting the pleasure of her wearing them.

    1. Hi Macs,
      Wow…that sounds really fun and sexy! I had not thought of wearing them in that way. With a wrap dress, you would not really see them, however with a longer skirt with slits, it would show a little “attitude”!
      Thanks for your male perspective and great ideas~

  37. Have any of you seen the newest UGG boot for Fall 2009? Now, before you groan — and say UGH to Ugg — look @ it – even shown in the Sept Vogue. The boot is called Highkoo. It is a marvelous flat heeled sueded boot. I think it is offered in 4 colors–the two freshest colors being a marvelous pale silvery grey and their amber brown.

    At my age – the concept of a 5 in high heeled boot wandering up to my sagging sighs makes me groan and giggle @ the same time.

  38. No. At 5 feet tall and 42 years old, only a career change to piracy would cause me to consider these boots. I would need the broad sword to deal with the comments.

• powered by chloédigital