“I am super excited about the over the knee boots trend this Fall, but I don’t know what to wear them with! Can you help me figure out what to wear with over the knee boots so I don’t look short and fat and/or ridiculous?! Help!”
(Susanne in New Jersey)
I’ve received several emails like this, asking what to wear with over the knee boots. The answer is easier than you think! Since over the knee boots are a trendy item this season, you can wear them with a lot of things and get away with it. You might not be so lucky next year or the year after, so take advantage of their immense popularity and wear them with everything you can.

Obvious choices are of course dresses or skirts that fall about 1-3 inches above the top of the boots (or about 4 inches from the top of your knee cap.) Wear tights, leggings or thigh high socks in a complimenting color. You can also tuck your skinny jeans or Ponté Knit Pants into your over the knee boots.
Be careful when choosing a pair of over the knee boots. Make a mental list beforehand of the items in your wardrobe you can actually wear them with, especially if you are going to spend more than $40 on a pair.
I also get a lot of emails asking “Am I too short to wear over the knee boots?”. The answer is no! You just have to know how to wear them properly and get used to looking to yourself in the mirror wearing these statement boots. When wearing over the knee boots with dresses and skirts, match your tights or leggings to the boots or choose thigh high socks in a complimenting color so you don’t have any visual breaks. This will help give you a leggier feel. Avoid the urge to get over the knee boots with very high heels! While you might like the extra inches to your stature, you risk looking very tacky at best. If you feel you must wear heels, look for thick stacked heels or wedges. Just any type of heel that has more substance to it than a thin stiletto.
Here are some more runway photos for more outfit inspirations…

Keep your silhouette long and lean by pairing with a tunic or long boyfriend jacket that ends just below your butt. Cinch in your waist with a skinny little belt. Create interest by adding texture and richness like suede, chunky knits, and leather. Avoid too many contrasting colors.
You can get the look of over-the-knee boots by wearing chunky, knee-high socks with regular knee high boots or layer over dark tights.
Look to celebs like Lindsay Lohan, Kim Kardashian, Kate Hudson, Vanessa Hudgens, Miley Cyrus and Kate Moss for celebrity style outfit ideas. Check out J Lo and Ciara rocking over the knee boots below…

So many possibilities! And from what I’ve seen, over the knee and thigh high boots look great with just about anything. I mean, I’m not loving J Lo’s ensemble above, but Kate Moss and Kate Hudson look fabulous!
What do you think you’ll try wearing over the knee boots with? Do you have any outfit ideas?
Although I am totally loving this trend, I feel you really do have to have a slimmer build to pull it off. I feel that it creates the same silhouette as skinny jeans and I can’t pull those off either. Hey no worries though, it’s better to know what works for your body then to jump on every trend bandwagon. :)
I love the over the knee with mini skirts or dresses. Super sexy. I think the key to pulling off the look is to make sure the boots fit snug above the knee. If they are too loose and sloppy, it ruins the whole chic look.
Also, remember that the eye will be drawn to wear the boot ends so make sure it’s not at the widest part of your thigh!
In my opinion, Kate pulls off the best “every day look” that is wearable for a typical busy mom.
I really think that almost anyone could pull this trend off if they nab the appropriate shape/style for their figure. Great post!
LOVE this trend! And a great round-up of inspiration images too.
I nabbed a pair by chloe last month and i have been wearing them non-stop. especially love how they look when worn with a blazer a la Kate Moss.
Finding a soft, comfy pair is key–if they’re stiff they’ll constrict your movement because there’s so much material!
I’m loving this trend. I have a flat pair by Report that I love. I tend to wear them with dresses and tights or leggings. It’s a great way to style an otherwise boring outfit.
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Hi I love the look of OTK boot. I have a Jimmy Choo pair with fringes that i purchased a couple years ago. My question is are OTK boots just a trend or is this a style that can be classic worn year after year.
I want to purchase another flat pair but afraid, because i don’t want to spend the money for it to just be a trend this season. thank you
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I love them! I think the flat ones are the way to go. I hate flat knee high boots but the thigh high boots make any outfit 100x better. The high heel thigh highs are a little to much. Reminds me of a hooker.
I love the over the knee boots you featured!!! You can also pair them with over the knee socks over legging instead of skinny jeans. I have a great selection of designer over the knee socks that I design…. http://www.sweetmarcel.com
This blog is very nice and informative. it is pretty hard task but your post and experience serve and teach me how to handle and make it more simple and manageable.
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I love thigh-high boots but unfortunately I didn’t get a chance to pick up a pair last year so im hoping that theyll stick around long enough until this winter so i can fiiinnaly get a pair lol
My wife absolutely loves her boots. I reckon she has a pair for every occasion as no matter what outfit she wears there is always a pair of boots to go with them.
One thing to remember before you buy any tall pair of boots is to measure your calf and check the shaft circumference of the boots. Many of these boots are built for people who have no calves to speak of. People with powerful legs may have to search a lot harder in order to find a pair that fits.