How to Wear Over-the-Knee Boots

Posted in Daily Outfits, Fashion.

wearing over the knee boots

Over-the-knee boots have a bad rep. I blame Julia Roberts in Pretty Woman for their association with prostitution. I mean, that DVD cover is iconic. Quite frankly, I think those boots were the ‘big mistake. Huge’ in that film.

For many, over-the-knee boots are thigh-high, in shiny patent plastic with a spike heel, teamed with questionable attire. They’re a bit tacky and not very classy, bought on market stalls where they hang clipped together at the top, swinging in a November breeze.

It’s a sartorial stereotype that needs stamping out, because over-the-knee boots are actually rather lovely, and totally practical for winter. See here…

wearing over knee boots

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Dress, Primark | Jumper, Uniqlo | Leather jacket, Michael Kors via TK Maxx | Tights, Primark | ‘Tanty’ boots c/o Bertie | Necklace, ASOS | Bag, Mulberry

The lovely folks at Bertie sent me these over-the-knee boots earlier this week and they’ve barely been off my feet since. They. Are. Gorgeous. Black leather (no hi-shine materials here), flat and slightly slouchy, they’re perfect for pounding the pavements in all weathers. Plus, the longer length means there’s more leather to cover your legs, keeping them nice and warm when the wind’s blowing.

how to wear over the knee boots fashion blogger uk black leather knee high boots

I think the key to successfully styling over-the-knee boots is to keep things casual. With a bodycon dress and no tights, even this casual version will look OTT, so stick to daytime attire. Here are a few ideas:

  • Dress them down – wear with cute tea dresses or classic denims and a snuggly jumper for serious style points
  • Don’t flash the flesh – wear with tights, leggings or trousers for a laidback look
  • Find your fit – any boots that cover the calves can be tricky to fit, but you really don’t want to cut off the circulation to your thighs. The ones I’m wearing have a handy adjustable buckle at the back to give you more or less room up top
  • Go for higher hems – make sure the hem of your dress or skirt sits mid-thigh rather than on the knee, and wear with thick tights
What do you think of over-the-knee boots? Would you wear them?


Kira Walker

Oh my these are beautiful! I would definitely wear them and agree dressing them down looks great. You’ve made a wonderful outfit, contrasting the feminine dress with the leather jacket & boots :). Might I ask which lipstick that is you’re wearing?

I have an old faithful pair of grey leather boots from NEXT that I live in so will have to perhaps put these on my Christmas list 🙂

x Kira

Mathilde heart Manech

It’s so true. I always avoid the ‘over knee’ category and it’s all because of Julia Roberts *shakesfistatsky*
They look lovely on you. Really like your Primark dress too 🙂


These boots are lovely! Nothing like the image of what the words ‘over the knee boots’ conjures up in my mind. Still dont think I’d be able to pull them off though 😀 x


Hi Emily, yes it is! Got it a few weeks ago so they should still have it in. There’s a navy blue one too.


They look lovely on you but I always feel that even knee high boots make my legs look stumpy so I don’t think I’ll ever be brave enough for over the knee!

Tiffany Siladke

I love over the knee boots! Mine are gray suede and I love them. I think wearing them casual is the best way, but they can be dressed up with the right outfit and accessories!


Love the way you’ve styled these boots. I used to own a pair of flat, black suede over the knee boots and loved them, even shed a lil tear when the wet weather/snow of last winter ruined them.


I do quite like them, but I tend to find that flat ones work best for dressing down. I do also have heeled over-knee boots which work fine with dresses which are a little above knee length to avoid the tacky ‘too much flesh’ mistake.
(I won’t talk about the patent ones!)

Maria Fallon

I LOVE this outfit and I cannot believe that dress is Primark! I have been looking for some flat OTK boots for a while now and these look ideal, I will have to check them out!

Maria xxx


Jen, we are those specs from? I kinda need some new ones andthey are what I’m looking for! PS. I’m loving your make up glasses for girls with classes! jane

over the knee boots

Pretty woman certainly gives a negative impact for over the knee boots but if we see the opposite side of this, it also gave the platform to boots that everyone would know about this category of boots…..


i so much love over the knee boots, are so versatili and always on fashion…i love your photos, great advices…


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