5 Ankle Boots Outfits for 2026

All right, I’ll admit it. In recent years, I haven’t been a big fan of ankle boots. Maybe it’s because I live in L.A., and most of the time, they feel too severe. My husband even bought me a very nice pair not too long ago, and I exchanged them for sandals. “What am I going to do with ankle boots?!” I thought. Aside from a geographical aversion, my second admission is that I partly returned the boots because I really wasn’t sure how I could wear them in a way that felt new and interesting (i.e., not with my typical jeans and sweater uniform). Sometimes, all you need is a little inspiration to change your tune.

For one, there’s no shortage of relevant ankle boot styles in 2026. The top can be wide, fitted or stocking-like. The toe: pointy, square, round, or somewhere in between. It doesn’t matter if your boot is flat, heeled, utilitarian, or dressy, either. The looks that I found myself drawn to are all incredibly varied. A maxi dress with a pair of sleek, pointy toes peeking out from underneath. A Fair Isle sweater and felted wool hat with a sturdy heeled ankle boot. In 2026, it’s about finding the style that works for you, not the other way around.