How to Wear Over-the-Knee Boots

I remember when over-the-knee boots came on the scene two years ago. There were about a thousand websites telling you how to wear them “without looking like Julia Roberts in Pretty Woman.” (For the record, people, prostitution is illegal, but saying the word “prostitute” is not. Stop giving Julia a hard time.) Anyway, most of those websites were just trying to convince you to buy OTK boots and threw in some very vague advice on how to style OTK boots, advice that was helpful if you happened to be a supermodel.

Now that it looks like over-the-knee is here to stay for awhile, I thought I’d share not one, not two, but eight tips for styling these boots, with 2 actually-worn outfit examples of each. Yes, that’s right, SIXTEEN outfit ideas for your non-prostituty footwear. Now let’s get down and dirty, but no kissing.

1.  Monochrome Tights & Boots

You know how your legs looks super long when you wear nude pumps with your dresses in the summer? Well, this is the cold-weather version. And it’s more comfortable, too. The boots I’m wearing below (similar styles here and here) are totally heel-less, but with a shorter skirt and black opaque tights, they’re still very leg-lengthening.

2.  Tunic Sweater & Leggings

On cold weekends, who doesn’t love getting comfy in an oversized knit and some leggings, right? Well, if you have to leave the house, adding over-the-knee boots to the equation makes you look instantly fabulous without subtracting comfort.

(Both of the boots below are Franco Sarto.)

3.  Layered Button-Up and Sweater

A classic shirt / sweater combo is one of my favorite go-to looks for work, but it’s also one of a million other people’s favorite go-to looks for work. Statement boots let me (and you) maintain a reputation as the coolest girl in the office.

4.  Bare Knees

For the fall months when it’s chilly in the morning but you’re still putting off wearing tights, over-the-knee boots keep most of your legs warm. Plus, I think the little sliver of skin is kinda cute. Maybe even sexy. But not street-walker sexy.

5.  Just Add Leather

When you’re ready to take this trend to the next level, feel free to wear your leather jacket (or skirt) with those sexy boots. As long as your sexy boots aren’t fire engine red, patent leather platforms, I’m confident you can pull this combo off.

6.  Plaid Skirt

I call this the rebellious school girl look. I love a plaid skirt but I always worry it looks like part of a Catholic school uniform. I’m pretty sure OTK boots aren’t nun-approved, so I figure they’ll prevent people from asking me why I’m not in class, young lady.

7.  Skinny Jeans + Anything

One of the reasons I love over-the-knee boots is that they let you layer like crazy over the part of your body (or, at least mine) that gets the coldest. It’s amazing what a difference that knee coverage makes. On really cold days when I wear my OTK boots with jeans, or even with tights and a skirt, I wear knee-high socks underneath too. Super cozy.

8.  Contrasting Tights

I saved this one for last because it’s a little more daring, so it might not be for everyone. But if you have any tights with fun colors or patterns that you’re unsure of, wearing them with really tall boots means they have a less intense impact. So maybe this isn’t such a daring option after all!

Thanks for tuning in for the latest episode of my How to Wear series! If over-the-knee isn’t your thing, you might get your kicks from my How to Wear Ankle Boots post instead. Otherwise, pin this for later and shop some boots below to get started.