New trend: Thigh High Boots
Hello Glam Gals,
Do you think the new thigh high boots for Fall 2009 are age appropriate for women over 40?
Thank you for your help.
~Jenifer G.
Hi Jennifer!
Great question, since we are seeing that thigh high boots are a big trend for fall. This is tricky because there are a lot of variables here. The thigh high boot is a very young and sexy look, so it is hard to pull it off after 40. However, we have seen women of all ages pulling off this trend, but it is a delicate and tricky one for sure.
If you are excited to try this new trend, here are some things to keep in mind:
- You should be on the thin side have slim legs and thighs to wear this look.
- You need to be careful on how to pair your boots with the right outfit. Tight jeans or longer skirts are your best bet to get the right effect.
- You will need to be picky about the style of boot your choose, otherwise it will look like you’re trying too hard. (More like you are wearing a costume than a trend.)
- The fit and style of your outfit is key – anything too tight and revealing could look smutty.
We imagine that the women over 40 that could pull this off, are on the creative and festive sort! However, if you really do want to partake in this trend, we recommend you
- Choose a simple style that does not have a lot of laces or hardware.
- Stay away from patent or shiny thigh high boots, or you’ll look like a hooker.
- Be sure to wear dark opaque hose so there’s no leg between the hem of your dress and the boot. Here’s a good example of flat heeled boot from zappos.com:

Bottom line: Are you wanting to try out a new trend, pick up a younger guy or just channeling your inner biker chic?
You weill need some confidence and good dose of style to pull this look off now that your over 40, or you will end up looking silly instead of chic.
Are you thinking of trying this look out this fall? If so, we want to hear your comments below!







I forgot to say that I have to wear them with my legwarmers underneath, otherwise they slip down.
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!
Flat or low-heeled riding boots with jeans are an entirely different story from the pic you posted of the “lady” in the white mini-skirt with the thigh high black happy hooker boots. Simply. No, they aren’t appropriate unless you are out trolling for the night or have no common sense whatsoever of age-appropriate dress. What looks good on Madonna DOES NOT translate to real women. And if you have to use the word “Cougar” or “rock it” to justify wearing that’s probably a sign you shouldn’t be wearing it either. As for UGG’s, my neices and nephews laugh hysterically at women over mid-20′s wearing them. They laughingly call them FUGGLY! for a good reason. If it’s a “trend” you see teens and college girls buying, you should NOT be lining up behind them in Nordies to buy the same thing. Whatever happened to women in their 40+’s plus having dignity and style in their dress and decorum? It seems like everyone wants to try to dress like the “Real Housewives of the OC” now and instead they just look like pathetic old Cougars. Sad. And remember ladies just because you are turning heads, it’s not always because you look good, sometimes they are just turning their heads in shock and to get a second look and say to their friend “Oh my god, I can’t believe she’s wearing THAT at her age! What? She doesn’t have a mirror?”
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.
Hi Heartly,
We don’t mind women wearing trends, as long as they are age appropriate. We think there are LOTS of different comfortable casual boots out there. We think Uggs are clunky and because so many young kids wearing them that they can look a little silly on more sophisticated women. However you make a good point about following trends. We do like to follow them, like gladiator sandles, ect..
However,Clogs are in style too, but we are not big fans of them either.
And on the other side of the coin, we have seen women in their late 60′s with thigh high boots that look terrific, too…
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).
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!
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…
Hi Judy,
Yes, so right!!!! The shiny boots really say, “trashy”… Being 5’9 you will rock thigh high!!! They are starting to show them already for fall, and are going to be HUGE we think!!
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!
Hi RockCandy girl,
You sound like you ROCK!!! You will be seeing the thigh high boot coming on STRONG…this fall!
We assure you, you will not be alone! Deborah got a pair last fall and I’m going out soon to get mine!! Can’t wait!
What do you think about a 40+ woman wearing motorcycle boots, as they are so in this season?
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.
Hi Bianca,
Great comment and it makes us realize that the word the word “age-appropriate” needs to be defined. We are going to write our next post on that topic!! Age-appropriate means different things to different women! It can mean dressing too old or too young. As far as our “take” on thigh high boots… you must have misunderstood our point because we never put a number on how old you can be to wear certain styles, just the opposite…we want women to feel wonderful in their clothes!!