Wide-Fit Chelsea Boots Shopping Guide

All wide-fit ankle boots are cute, sure, but wide-fit Chelsea boots just hit different. And for good reason! They last from season to season without going out of style—but they’re somehow trendy at the same time. Quite frankly, it’s a sartorial mystery (and one we don’t intend on solving any time soon). After all, when a bootie defies all logic and remains on-trend year after year, there’s no need to question why. We’ll stick to just enjoying Chelsea boots in all their glory, thanks.

During any season—but especially fall and winter—reaching for a pair of wide-fit Chelsea boots is a no-brainer. You can spot them on every NYC gal anywhere you go, but it doesn’t make the style any less desirable. Because unlike the phenomenon that was the leopard print midi skirt (What a time, right?), Chelsea boots have staying power. So go ahead and pack your closet full of them—even if you already have a few pairs already.

While the most classic Chelsea boots are typically in sold black hues—and many times leather or faux leather—there are plenty of other options out there. We’re talking fun and bold colors, statement prints, and even glittery beauts. (!) Your favorite brands have taken the Chelsea boot style and run with it, creating so many gorgeous picks for every occasion. Go simple or go maximalist; the choice is yours.

Whichever pair (or pairs) of these wide-fit Chelsea boots you choose, though, you’re sure to find hundreds of ways to wear them. The versatility of ankle boots is endless, and your closet will be better for it. So treat yourself, boo. This trend is both fashion and function at the same time—and you can’t beat that.