21 Chelsea Boots You'll Fall In Love With

Say hello to your new, sleek, square-toe Chelsea boot.

Croc-embossed boots add a little something extra. Wear this style upper tucked into pant legs or alongside flowing midi dresses.

The Chelsea boot's edgy twin. The cutout heel will add a subtle flare to an otherwise basic look.

The suede of these tan Chelsea boots will seamlessly fit in with your autumnal wardrobe. Cue the pumpkin spice!

Comfy? Yes. Durable. Check. These rugged Chelsea boots have a molded footbed and a can-do attitude—what more can you ask for?

Two qualities I ask for in my Chelsea boots this season: The shoe has to have a thick platform and a heel, so my 5'4 frame doesn't look weighed down by my footwear. This pair from Free People is the answer to my search.

Swap your traditional rain boots for this rugged Chelsea boot version.

No need to over-accessorize when your Chelsea boots come equipped with insets and studs like these.

Take a chance on something new this season, they'll look sharp with fall's cozy knits and can be worn well into winter.

Expect compliments every time you slide on a pair of Thursday Boots' Chelsea boots with its statement pull tab in the back.

Contrast stitching and a stack lug sole merges outdoor sophisticated with everyday elegance.

These Chelsea boots have a matte finish and are suited for rainy days, though you can wear them even when there's not a cloud in the sky. I love a boot that does double duty.

This is not your run-of-the-mill Chelsea. A burgundy patent leather exterior and a bold silver buckle kicks it up a few notches.

These boots are designed to keep your feet warm on even the coldest of days. Dr. Martens' boots are basically a winter essential, so it's about time you got one for yourself.

Only Off-White can design a tag in the back that doesn't take away from the shoe, or make you want to rip it off. This boot is perfect for someone who has an eye for designer goods, but doesn't want something logo heavy.

A good alternative to wearing heels in the winter, if you like height in your footwear, is to slip into this boot from Paige. It has a 3-inch heel and 1.5-inch platform, so you can feel comfortably elevated amongst your peers.

If you're looking for a boot that you can wear all year long, this pair is for you. Tan shoes really pop against the dark colors you wear during the fall and winter, and perfectly match any of your spring and summer outfits.

A translucent sole gives these otherwise simple boots a modern twist. The higher rise on the ankle will keep your feet dry as you stomp your way through the winter season.

There's no doubt the stitching on this shoe is what gives it the ultimate cool-girl look. It's Proenza Schouler's best-selling Chelsea boot, which means I, you, everyone, need it.

I can't say enough great things about Marc Fisher's pointy-toe Chelsea boots, which come in nine (!) different styles. They're insanely comfortable and look great when you're heading to those post-work drinks straight from the office. Pick the ivory or snakeskin if you want a pair you can wear year-round.