Best Boots to Wear With Leggings

Today on, I’m going to go through each of the best boots to wear with leggings, how to wear them, along with the top leggings to choose (and avoid!) with each.

Leggings with boots are a classic combo. I love pairing them from fall through spring for easy go-to outfits! I choose a thicker or thermal to tuck into boots during the frigid months.

From ankle boots to thigh high boots to combat boots, there are lots of boots to wear with leggings. Here are some of my favorite boot styles with leggings and how to wear them.

I prefer lower or flat-heeled high boots for daily wear, like Stuart Weitzman's 50/50 high boot, which looks sleek and classy.

Over the Knee Boots with Leggings


Opt for leather or black leggings, with black lug sole Chelseas and an oversized shirt or tee.

Chelsea Boots with Leggings


Stick to darker colored leggings with cowboy boots that have deeper hues. With lighter western boots like beige or white, you can choose any color you like!

Cowboy Boots with Leggings


How to wear hiking boots is simple. You can play up the sporty aspect of the boots with thermal leggings, a tight turtleneck, and a fitted puffer.

Hiking Boots with Leggings


All black riding boots are in. Whether rain boots or made of leather, these will look great with dark toned leggings and jeggings.

How to Wear Riding Boots with Leggings


Swipe up to see all the recommendations!