How To Wear - January 24, 2019

How to Style Over-the-Knee Boots Without Trying Too Hard

I have a love/hate relationship with the over-the-knee boot trend. Anyone else feel me?! On one hand, they can be super cute and sassy, and when styled right, I LOVE how they look. On the other, they can go from classy to trash really quick and sometimes I feel uncomfortable wearing them. It’s probably because I have more traditional, classic, everyday style to begin with, but y’all know I like to throw some sass in here and there!

After a serious Pinterest and Instagram rabbit hole of OTK boots a while back, I realized that I DO love how they look – it’s just soooooo crucial to know how to style them. At least for the style I’m going for (traditional, classic, every day with a bit of sass, duh). I know a lot of y’all probably feel the same, so I wanted to break down what those crucial steps are when styling this trend. Hope they’re helpful!

Start with monochrome

If you’re intrigued by the boot style but are still kinda uncomfy with them, start with monochrome black on black. Black leggings or jeans + black OTK boots and you have a super cute outfit (like this or this). Plus, it’s very flattering!

Be careful with hem lines

Mini skirts, short dresses, or anything with a “flirty” hem is not going to work with OTK boots (again, for MY style). It might look cute on some girls, but for me, the mix of a short hem with high boots just feels too revealing or even scandalous for me to feel confident. I really only wear hems above the knee with bare legs and these boots if there’s like an inch in between and usually a looser fit (like this). If it’s any higher than that, I 100% have tights on for additional coverage (like this outfit!). Or, they can look cute with a midi dress or skirt for a more boho look, though I haven’t really done that much.

Cover your backside

Y’all know how leggings or leather leggings feel more comfortable and conservative when you cover your booty? I feel it’s the same with OTK boots. For the most part, I cover my booty when I’m wearing them. Maybe this sounds weird, but it’s basically letting the boots be the focal sassy part and then leaving everything else on your body more conservative. So I won’t really wear skintight bottoms without coverage over my bum + OTK boots (like this). Does that make sense?


I also like to think of what I’m pairing the boots with. For example, this outfit is cute without the jacket, but it’s a lot of sassy elements, right? Tight jeans, a tucked in top, and boots – even though I’m not really showing skin, ha! But, I chose a classic collared coat to tone done the sass. The jacket balances the rest of the look and adds a more traditional approach that I feel comfortable in. For drinks with girls or a date night, I would probably take the jacket off and maybe add a cute cardigan or duster!

OK those are most of my tips! You can also go with a thicker heel if stiletto heels feel like you’re trying to hard with these boots, but that’s up to you.

Here are some of the OTK that I love most and feel like they’re a good option for everything I talked about here! :)

Outfit Details