how to wear over-the-knee boots

How to Wear Over the Knee Boots with Skirts and Dresses

About a hundred years ago or so, someone asked me if I could give them some tips on how to wear over the knee boots – which I tend to wear fairly often at this time of year. 

Now, my initial reaction to this was to say, “Well, no, not really.” Because the fact is, I don’t actually have “some tips” on how to wear over the knee boots. I have ONE tip: and that doesn’t really seem like much, does it? Then I got to thinking that, you know, for people who are a bit worried about wearing thigh high boots (Which, let’s fact it, can have some serious ‘Julia Roberts in Pretty Woman‘ connotations for  a lot of folks), maybe that one tip is all they really need?

So here it is: my absolute best advice on the wearing of thigh high or over the knee boots with skirts and dresses:

Always make sure your hem is longer than the top of the boots.

So this…


Collectif dress; Moda in Pelle boots*

… will be easier to wear than this:

over the knee boots with short dress

Zara dress (old); same boots

So, two dresses, both alike in… well, not dignity, exactly, but they’re both the same colour and shape, anyway. While you don’t have to make sure your dress is QUITE as long as the first one, however, if you’re new to over the knee boots (which I’m guessing you are, or you wouldn’t be reading this), you’ll probably find a dress which at least covers the top of the boots easier to wear than one which doesn’t. It’s not that one look is wrong and the other one is right: I mean, you can wear the boots with the shorter dress if you like, because it’s not the 1950s, is it?

But for me personally (and please note, this is a preference, not a “rule” – I’m not trying to tell you what to wear here, just sharing what works for me!), the beauty of over the knee boots is that they create a totally streamlined look under your dresses and skirts: so, rather than having a line drawn across the top of your knee, where the boot ends, and then another one across your thighs, where your dress starts, you just get one long, uninterrupted line, which has the effect of making your legs look longer and the silhouette of your outfit a little sleeker. The “chopped up leg” effect I’m taking about is even more apparent if I ditch the tights for a second:

how not to wear over the knee boots

Now, it’s not like this is the most risquΓ© look in the world or anything but, well, I’m from a small town, and if I went out like this, people would look at me like THIS:

shock horror

Then they would clutch their pearls and say that young ladies do not show their bare thighs in public, thankyouverymuch. It actually still IS the 1950s in some small towns, now I come to think of it. That obviously isn’t a reason not to wear what you like, obviously, but the fact is, I don’t like this: not only is it just not “me” (I actually died a little inside when I was wearing it for the photos), I don’t think it’s particularly flattering, either. See that line of pale flesh between the boots and the dress? (Er, don’t look TOO closely at it, if you don’t mind…) That line is exactly what I was talking about above: it’s cutting my leg in half, which makes me look shorter, and also draws attention to my thighs, which I REALLY don’t want. (No, seriously, stop looking at them, I won’t tell you again!)

You can fix this in three different ways, two of which you can see above:

01. Wear a longer dress, which covers the top of the boots

02. Wear dark coloured tights, which are the same colour as the boots


03. Wear longer boots:


River Island boots (similar)

These are thigh high boots rather than over the knee ones, so they close the gap between hem and boot top, once again creating that more streamlined silhouette. My personal preference would always be to lengthen the skirt rather than the boots, and close the gap that way, but like I said, that’s just me: you do you, and don’t listen to me if you don’t want to.

Although both of the dresses I’m wearing here are pencil/bodycon styles, thigh high or over the knee boots work just as well with any other shape, and I frequently wear them with circle skirts/dresses, too, as you’ll see if you take a look through my ‘outfits’ archive.  The same tip applies to any style of dress or skirt: I just make sure the hem covers the top of the boot, et voila. While the style of dress doesn’t really matter, however, the type of BOOT you’re wearing DOES, and my advice here is also pretty simple:

With dresses and skirts, make sure your boots are a close-fitting as possible. 

Loose or slouchy over the knee boots can look great over jeans or leggings, but two things happen when you try to wear them with skirts or dresses. First of all…


Er, I SWEAR I have ankles and calves – you just can’t see them, because these flat, slouchy boots have transformed my legs into a pair of stumpy tree trunks, with absolutely no definition whatsoever. This would be less of an issue if I was wearing these over jeans, say, because you’d see more of the leg, but with this dress, they’re just not very flattering. They’re also not nearly as comfortable as you’re probably thinking loose-fitting flat boots would be, because here’s the other issue you get with this style of over the knee boot, worn with a dress:

the trouble with boots and dresses

See the way the dress is catching on the top of the boot? To be fair, these particular boots are slightly too short to count as true “over the knee” boots (they were the only ones I had that were the right kind of shape – or the wrong kind of shape, as the case may be…), but this also happens with taller boots, and it drives me crazy. It doesn’t look particularly great either, so while I know it can be easier said than done, it’s better to hold out for a pair of boots that fit your legs snuggly enough for this not to happen (but not SO snug that they’ll cut off your circulation, obviously…), than buy a pair that’s too loose.

And there you have it: Amber’s quick guide to wearing over the knee boots with skirts or dresses! As I said, this is pretty basic stuff, and I don’t claim to be an expert in any way, but it’s something I’ve been asked about, so I hope it helps someone!

 how to wear over the knee or thigh high boots

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  • The Other Emma


    Love the horrified villager look, think that one’s my favourite πŸ˜‰

    March 2, 2016
    • Sarah Sharpe


      So is it ok to wear leg hugging over the knee boots that are flat with a sleevless sheath fall dress ? The dress is below knee length.

      October 12, 2018
  • Hi Amber, A good feature and good tip on how to wear knee high boots. Any knee high boots I wear just cover my legs entirely. It look weird on me. xx

    March 2, 2016
  • Ooooh I love your green dresses! i also love boots but only have a couple pair since I live in a warm climate. πŸ™ I’d love to get some of those over-the-knee boots!

    March 2, 2016
  • I think if you do shorten the skirt, you should go 60s mini and keep the boots flat rather than heeled to avoid the Pretty Woman effect… But I mostly say that because I’m in love with some flat 60s style boots by BAIT at the moment and can’t stop thinking about them πŸ˜‰

    March 2, 2016
  • Awesome post – I always struggle with what to wear with my over the knee boots because I was a bit hesitant to do the long skirt with boots thing. Not sure why, but seeing your previous posts where you’ve done it spurred me on to try and it and I love it! I mostly wear mine the “lazy” way with jeans, but I do occasionally go for a slightly higher hem, but always black tights in between πŸ˜‰
    And the shock if you bared your thighs – I know it would be exactly the same around here too! πŸ˜€

    March 2, 2016
  • I do love the OTK boots with the shorter dress and tights on you, but if it is not a look your comfortable with then no question go long in the dress. But you do look amazing

    March 2, 2016
  • My favourite styles are the one with the socks and the short skirt and the one with longer boots. I guess I just really love that dress!

    March 2, 2016
  • Myra


    Very good advice, love the long dress

    March 2, 2016
  • I’ve never really thought of covering the “over the knee” part of these boots! I feel like at this time of year, every inch of extra material helps keep me warm so I’d definitely be down to try these.
    xx, Pia

    March 2, 2016
  • I wear OTK exactly so I can skip tights, would never wear both πŸ™‚ I do prefer to wear them with shorter skirts, but with a loose, flowy dress. Everything tight fitting and bare tights doesn’t feel comfortable for me. Leonie from ohhcouture also loves this look, if anyone is looking for inspiration πŸ™‚

    March 2, 2016
  • Andrea Thomas


    With weather like today I really wanted my lovely long boots AND thick tights but I was afraid of the whole Pretty Woman look- not that I have ever been mistaken for Julia Roberts. Lol. I’m trying your suggestion with a long midi tomorrow. Thanks Amber..

    March 2, 2016
  • Great tips! Love the color of your dresses, they look amazing with your coloring!

    xx, Elise

    March 2, 2016
  • Awesome post! Love the colour of your dresses. xxx

    March 2, 2016
  • Michelle Adams


    Hi Amber, thank you so much for sharing this simple but amazing tip with us. I for one would not have considered wearing over the knee boots with longer skirts and instead would have gone with a much higher hemline, probably much to the consternation of the female inhabitants of small Scottish towns. You look totally amazing in your green pencil dress and the similar style longer length wiggle dresses you’ve teamed with over the knee boots in numerous blog posts in the past. Whilst such outfits may meet with favour with demure expectations of the aforementioned small town ladies, they are in my opinion no less stylish and dare I say it sexy for it and certainly a look I’ll be trying to emulate myself. I notice your Topshop “Barley” boots fail to feature in this post, I hope they have not been discarded in a cull of your extensive footwear collection. Hopefully you’ve merely chosen not to feature them this time so as to prevent further unauthorised use of them in Ebay auctions. If it’s any consolation, I bought a said pair of “Barleys” on Ebay primarily because they looked so good on you x

    March 3, 2016
      • Michelle Adams


        Sorry to hear that I sincerely hope you don’t think that’s what I was doing. Sadly longer length boots will probably have those “Pretty Woman” connotations and attract such undesirable non fashion related interest in them. Maybe your more demure way of wearing them may go some way to redressing that.

        March 3, 2016
  • Great fun post as well as some great tips! Really enjoyed reading it. You look stunning ☺?
    Sharon from

    March 20, 2016