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.
Ahead, check out the five ankle boot outfits that are seriously making me reconsider my return.
Sleek and Easy
When worn with your best basics, patent-leather ankle boots take center stage. The muted mocha color of the trench coat is a nice departure from your typical black and beige, too.
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Après-Ski
If the name of your game’s elongation, high-rise straight-leg jeans and heeled ankle boots are a winning combination. But it’s really about the layering and accessories, here. Tucking your printed cardigan into your jeans, a hint of a white turtleneck peeking out, and topping it all off with a hat and dark sunglasses keeps the eye guessing in a good way.
Subdued Sophistication
Styling ankle boots with shorter dresses is a slippery slope because it’s hard to get right proportionally. Normally, the scale is tipped way too far one way. That’s not an issue when you wear ankle boots with a maxi dress. Accessorized with a mild Western-style belt, this would be my go-to outfit formula for any and all cold-weather cocktail hours.
Old-World Fun
Your go-anywhere ankle boots are revitalized when worn with pops of color. I love the coordination of the red babushka head scarf, mohair gloves, and knit purse. Not to mention the checked puffer jacket. In 2026, colors, textures and patterns reign supreme.
Casual Elegance
I haven’t ventured into the fold-over boot territory since I wore aggressive Uggs in the early aughts, in large part because it was the era of skinny jeans and they could easily be tucked into my boots. But as evidenced below, fold-over boots actually look effortless with looser-fitting jeans, too. Paired with a structured bag and pretty coat, they'll make you both warm and very, very cool. PSA: Anouk Yve’s boots are Toteme, and Nordstrom currently has them on major sale.
