Zip-up, laced or, even worse, zips and laces, boots are a cold-weather staple that can sometimes be a lot of trouble to slide into. An easy solution? The elasticized sides on Chelsea boots are an easy-on, easy-off solution that’s pretty and polished all at once. It’s a borrrowed-from-the-boys look we get behind for just about every season, but this year, try pairing these wear-everywhere boots with some unexpected picks. Try a dress. Your go-to skinnies, of course, but slip them on with your wide-legged pants, too. Basically, wear them with everything for a little bit of masculine edge and comfortable cool.
Save: Gap Chelsea Boots ($98)
Steal: Duke’s Lotta Classic Chelsea Boot ($196)
Splurge: Thom Browne Black Leather Chelsea Boot ($948)
Images courtesy Gap, Madewell, and SSense