How to Wear Over-the-knee Boots

Image from CollegeFashion.net

Tall boots have been around for ages. In fact, I bought my first pair at least 10 years ago. And, every year the evil retailers come out with a new, updated style, and, well,  I NEED another pair of boots. There's tall pointed, flat pointed, flat round toe, wooden heel, brown, black, camel...ahhh the list goes on. So, I wasn't surprised when I spotted over-the-knee boots last Fall season. Believe it or not, I resisted but finally gave in to temptation this year.
The good thing: you don't have to be in your 20s to wear this style, really! And, even petite women can pull it off. Hilary Duff is only 5'2" and she's been spotted rocking this style.
Here's what I learned:

1. Don't buy over-the-knee boots that go up to the middle of your thigh. If you wanted to wear hip waders, you'd just buy hip waders, right? The most flattering tall boot hits either right below your knee or right above (like RIGHT above, not two inches above.) And, if you love the style but feel a little timid wearing them out, consider some that can be worn folded down below the knee.

Shiny, spiked and high--ICK!

2. Watch the heel. As I mentioned in THIS POST, the quickest way to stripper territory is to buy spiked heel, thigh-high boots. No matter how sexy you think this style is, run away! If you're going to try an over-the-knee boot, go with a flat or wedge heel. It's much classier and easier to wear.

3. Fitted or loose? For me, the more fitted the better. Many of the over-the-knee have an over-sized shaft. Personally, I think that just makes your legs look bigger than they are. A more fitted look slims the leg and elongates it. If you're petite and want to wear this style, go fitted. Otherwise, the boot will wear you.

4. It's all about proportion. Like all trends, you have to kiss a lot of frogs before you find your prince. I tried the Ann Taylor Loft Peter OTK boot and thought they swallowed up my leg. I could fit another person in there with me! I ended up with the Ann Taylor Loft Shiri Brown Suede boot. Here are a few styles I like.

ASOS Dune Bingo Suede Over Knee Wedge Boots

 

OVERRPAS OVER THE KNEE BOOT BROWN SUEDE

STEVE MADDEN

Ann Taylor Loft Shiri Suede Over the Knee Boots

The Ann Taylor Loft Shiri can be worn up over folded down.

Tory Burch Jack Boot 20% off at Bloomies right now!

Still confused about what to wear with them? I think they look best with skinny jeans and a slouchy sweater, tunic top or fitted blazer over a longer tank/tee shirt.
Skirts and dresses are trickier to wear with these boots. First of all, if you wear a mini-skirt with them, don't go too mini. No matter how many celebrities wear super minis and tall boots (and look awesome!) there aren't many people who can really pull off that style. Not to mention, said celebs are in their teens and early 20s. For anyone older than 25, a super mini and OTK boots gets you horrifyingly close to tramp territory. If your skirt is short (you can wear a mini, just not a SUPER mini), wear tights and tall boots.
Also, there should always be some skin showing between your skirt/dress and the boots. This is the most flattering look. Typically, a fuller, shorter skirt looks best, although you can get away with a sweater dress and tights pretty easily.
Got a question about whether or not an outfit works with OTK boots? Email me!