What to Wear With Thigh High Boots

Lately I’ve noticed that quite a few people have been arriving at the site having typed some variation on the phrase “What to wear with thigh high boots?” into Google, so I figured that was a clue that I should probably actually WRITE something on the subject of what to wear with thigh high boots. Well, I aim to please, after all.

So, what to wear with thigh high boots?

Now, as it happens, I’m a huge fan of thigh-high boots (Or “over the knee boots”, as you might prefer to call them. Because I’m relatively short, most of the pairs I own are, indeed, “thigh high”, but they’d be just over-the-knee on someone taller, so this post could apply to either of the two styles. ), so I headed over to my outfit blog to gather some photos to illustrate this post with, and as I scrolled through the images I realised I pretty much ALWAYS wear my thigh-high boots in one of two ways.

I wear them with pencil skirts/dresses:

what to wear with thigh high bo


What to wear with thigh high boots: pencil skirts

And I wear them with full skirts/dresses:

thigh high boots

What to wear with thigh high boots: full skirts

(I don’t ALWAYS wear them in the snow, by the way, and nor do I recommend it. The sidewalks and roads were actually clear of snow when these were taken: I was just standing in the few patches that were left, to get a better photo!)

I’m wearing the same boots in both of  these photos: they’re Topshops’s ‘Barely2’ boots, from a couple of years ago, and I would honestly be lost without them once boot season kicks in. Although these outfits are both basically variations on the same basic theme, they do serve to illustrate my main tip when it comes to deciding what to wear with thigh high boots, which is:

Make sure your hemline is lower than the the top of the boots.

It’s as simple as that, really. The main reason people find thigh high boots difficult to style, or worry about wearing them, is because of the “Pretty Woman” connotations they can have. Wear them with a skirt or dress which covers the top of the boots, however, and you get rid of that problem instantly: in fact the boots then become no more difficult to style than a pair of knee high boots. Make your dress or skirt a floaty one, rather than a form-fitting one, and styling the boots becomes even easier.

Some of you might be thinking here that wearing thigh-high boots in this covered-up kind of way kind of defeats the purpose: you can’t really tell that they’re thigh high boots, after all, so what’s the point? In my case, that’s not an issue: I don’t wear them BECAUSE they’re thigh high – I wear them because I like the sleek line they create under dresses, and the fact that they don’t cut the leg in half, the way shorter boots, do, or gape around the knee. If you DO want to make it obvious that the boots are thigh-high, however, there are plenty of other ways to do it, the most obvious one being to wear them with skinny jeans or leggings. I don’t have any photos of this look, because all of my current boots are too close-fitting to go over the top of something, but if you want to wear your boots this way, my main tips are to:

1. Choose boots in a fairly slouchy style

2. Make sure your jeans aren’t too bulky – jeggings can actually be a good alternative here.

3. Cover up your top half. Although boots-over-jeans is a totally covered-up look, it’s still quite a sexy one, so if you don’t want to stray too far into that “Pretty Woman” territory, go for looser tops or high necks, rather than something revealing.

What type of thigh high boot should you go for?

I deliberately choose photos in which I was wearing exactly the same boots with each outfit, and obviously my own preference is for high heels, especially when wearing midi-length skirts and dresses. Thigh high boots, however, come in a variety of styles and colour, and if you want to try the look, flat, slouchy boots are probably the easiest style to wear: they’re comfortable and casual, and look great with jeans or leggings: also, many of them can be folded down at the top, turning them instantly into knee boots, which makes them even easier to wear.

With all of that said…

… all of these tips are purely the way I personally wear thigh high (or over-the-knee) boots, and as you can see, I have… let’s call it a “signature style”, shall we. It’s kinder than just saying I wear the same things all the time. It goes without saying, however, that everyone’s taste is different, therefore there are as many different ways to wear thigh high boots as you want there to be. In a bid to balance things out a little here, I’m going to open this one to the floor and ask those of you who wear thigh high boots what you generally wear them with:

What would YOU wear with thigh high boots?


  • Hi, I like your post about thigh high boot and I personally like the first picture.You said that you’re relatively short, I would like to ask how tall are you? I’m 165 cm by the way and I’m not quite confident to wear thigh high boot. Could you give some advices? Thank you

  • You look amazing! Those boots are stunning, and really quite ‘fetish’ for a high street retailer (that’s in a good way). I love the pairing with the gloves, exactly how I would choose to wear them.

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