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.
… will be easier to wear than this:
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:
Now, it’s not like this is the most risqué 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:
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:
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!