Best Boots To Wear With Leggings, From Ankle Boots To Tall Boots

There are many great shoes to wear with leggings, but for Fall/Winter, it’s all about leggings with boots!

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.

There are so many legging types! To keep things simple, I’ll be focusing on these 8 types of leggings in this story. Simple black leggings are at the forefront.

You can wear your leggings casually with western-style ankle boots, or add an edgy look with black silver studded booties.

Classic Ankle Boots with Leggings


Combat boots with leggings – especially black cotton, leather, or suede leggings you can tuck inside – are best.

Combat Boots with Leggings


Slouchy black or brown suede boots are fun and have a more relaxed look with jeggings and simple black leggings.

Knee High Boots with Leggings


You can wear thigh high boots with leggings if you choose the right leggings style. Go for simple leggings that match the tone of your boots.

Over the Knee Boots with Leggings


I usually don't recommend a chunky boot with tight pants, but if an edgy vibe is what you're after, it can look fun.

Chelsea Boots with Leggings


Swipe up to see all the recommendations!