New Ways to Wear Your OTK Boots

Fashion / Tuesday, December 11th, 2018

I have to admit that when I considered buying a pair of OTK (over-the-knee) boots, I thought that I might be too old for them. Would I look like I’m trying too hard? Is this something that should be left for the under 30 crowd? My first recollection of OTK boots is from the movie Pretty Woman. Although Julia Roberts looked gorgeous as always, I certainly didn’t want to be evoking the Hollywood boulevard worker vibe.

Over the weekend I saw a CBS Sunday Morning interview and story featuring Ralph Lauren. I have always admired his style and how the Ralph Lauren collection has managed to stay current yet classic at the same time. Something only a true fashion OG can say got me thinking about my OTK boots, especially if I’m ever feeling a little less than confident. He said that clothes should never be about how they make you look, but how they make you feel. For example, when asked about the brand of plaid shirt he was wearing, he said he’d purchased it at K-Mart. He loves it because of how it makes him feel and all the memories he’s made when wearing it. Every worn spot or little distress mark is a reminder of those memories. His shirt, he said, is “…living proof of what I believe in.” He went on to say that a woman shouldn’t have to wear a label to prove she has taste. He said, “If you enjoy something, I like that, ’cause you’re expressing who you are.” 


As with anything #trendingnow, I go the cautious route and try not to blow the budget. I found this pair of OTK boots last season actually at Nordstrom Rack, and have enjoyed experimenting more with them this year. Scroll down to shop other brands I’ve found at all different price points to achieve a similar look and express who YOU are.

New Ways to Wear Your OTK Boots

Shorts! Stay with me on this one… Over the summer I bought a pair of ruffle hem shorts that were perfect for date night. I thought that I would be putting them away for fall and winter, but with my OTK boots I was wrong. The ruffle hem gives the shorts more of a skirt look anyway, so it just worked. Plus they’re black which helps dress them up a bit. I wouldn’t pair just any shorts with OTK boots, but I really liked this option. Funny side note – my SIL told me I looked like a sexy Hermione from Harry Potter. LOL!

new ways to wear OTK boots

See more of this OTK boot look on my Instagram here and here!

Maxi or long dresses are a little surprising because they do hide most of the OTK boot. But I like them paired for a couple of reasons. One – if your skirt or dress has buttons you can undo a few and create the effect of a slit. Two – OTK boots keep your legs warm so you can repurpose that summer dress that otherwise would need to retire for the season. Maybe I’m crazy, but I really liked how my dark gray OTK boots worked with this long dark blue button-front dress. I think all I’m missing is a menswear blazer. What do you think?

how to style over-the-knee boots with a summer dress

Styling OTK boots with long dresses on

New ways to style OTK boots on

My dress is from Urban Provisions in Helotes, TX. It’s another boutique I love and they ship!

Tried and True Ways to Wear OTK Boots

Jeans and a sweater are one of my staples this time of year. OTK boots make perfect sense (and even help keep my legs warm).

Leggings and a tunic are another way I’ve worn my OTK boots. I’ve talked about my love for fleece-lined leggings in a few of my travel posts, most recently for Paris in winter.

Shorter-length skirts and dresses are an obvious choice. I actually like it when I’m showing just a little leg between the hem and top of the boot. A sweater dress is a no-brainer, but go a little retro with it and style your hair and jewelry like I did. Hello, 60’s!

How to Wear OTK Boots with Sweater Dresses on

Styling OTK Boots with sweater dresses on

How to Wear OTK Boots with a Sweater Dress on

This mock turtleneck sweater dress is from Target and sold out, but I love this cable-knit option! My earrings can be found here.

The moral of the story…

  • Wear what you like that makes you feel good.
  • OTK boots don’t have to be expensive or even from a big named brand.
  • Shop your closet – drag out items from other seasons and see if they work. You can always layer up if you’re worried about warmth.

Shop OTK Boots

Thanks for reading, guys! I really appreciate it (and feel free to share)!

Xo – Erin

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