After months of sandals, slip-ons, and slides, the arrival of fall is bittersweet. Firmly on the “sweet” side of things, though, is the ability to wear Chelsea boots anytime, anywhere. The slip-on style has been a wardrobe MVP for a few years now, thanks both to comfort (no fussy buckles or spindly heels) and versatility (they go with just about anything in your closet).
That said, how to wear them with jeans isn’t always obvious—too long, and you get an unfortunate bunching situation; too short, and the sliver of bare ankle can look awkward depending on your pants. The easiest style to pair with Chelsea boots—which we’d bet you already have sitting in your closet—is a pair of skinny jeans that hits right at the ankle, so there’s no extra fabric gathered around the tops of the boots after you slip them on.
Another cut that’s everywhere right now, the cropped wide-leg or kick-flare, also works well with ankle boots, particularly ones with a slightly longer shaft so they disappear under the hem of the jeans—no tuck necessary. (See the photo above, plus several in the slideshow, to see what we mean.)
Of course, denim is hardly the only option—a well-worn pair of black Chelsea boots can be the perfect accessory to the more obviously sexy pieces in your closet: a leopard-print slip dress, say, or an ultra-short mini. The style is also ideal to wear with the pleated midi skirts and dark, moody florals that are trending hard this fall.
Hosiery-wise, you also have some options: Stick to ankle socks for a no-show look, opt for opaque tights when it gets chilly, or let a cute pair of socks peek out over top (I have mesh ones that I love, and prints are always fun, but athletic-style tube socks would actually be very Vetements).
Below, see 21 ways to wear Chelsea boots this season, whether it’s a statement metallic pair or your trusty black Blundstones.