How To Style Over-The-Knee Boots, According To R29 Editors

Boot season is year-round. From all-purpose knee-highs to Beyoncé-approved cowboy styles, boots are the unsung heroes of our wardrobes in every climate. They go with everything, are suitable for most occasions, and are often as practical as your favourite trainers. That said, some silhouettes prove to be a little harder to style than others.

Because of their stature, over-the-knee boots are a bigger commitment — not just monetarily but also because of how much real estate they take up in a look. Of the many factors to consider, material will determine their versatility: Buttery leather thigh-highs are more suitable for autumn and winter, while soft suedes and stretch knits are more year-round. Colour, too, is an important consideration. Neutral brown, black and burgundy styles are a safe bet for everyday wear, while a bright or printed boot can make a big statement with little effort. 

The cold weather has us reaching for our full-coverage boots more than ever. But if you’re feeling overwhelmed by the outfit options, we’re going to let you in on a little secret: The trick to mastering the look is styling around your boots. Refinery 29’s editors demonstrate how — and share how you can shop their ensembles — below. 

I instantly fell in love with these over-the-top, over-the-knee boots from the Larroudé x Markarian collaboration, especially for the holiday season. To keep the focus on the intricate patchwork detailing, I’ve been styling them with a red rain coat or a sand-coloured trench when I want all focus on the boots. — Irina Grechko, Fashion Director

My style is very utilitarian, but my boot collection? Brimming, darling. For me, over-the-knee boots are the star of the show so I only ever style them with one other “big” piece. In this case, I opted for a trench coat (it was freezing out!) on top of a midi dress with a slit, to show off the shoes. I pull them down a bit so they’re even more on display — and I like how the soft leather crinkles up. I also adore the shape; it’s very chunky, comfortable, and wearable. — Humeara Mohamed, Contributing Writer

When I wear skirts and dresses during the colder months, I’ll usually pair them with thermal leggings (Uniqlo for the win) or tights. What I love about over-the-knee boots is that they can literally double as pants (!), and, with the skirts-over-pants trend still going strong, I’m definitely going to be wearing them under midi skirts and dresses all season long. I’ll still layer with tights or leggings, but I like how the boots switch things up and make my outfit look 10 times cooler. I love this All Saints pair because of the block heel, which means they’re actually made for walking. — Ebony-Renee Baker, Fashion Editor