24 Chelsea Boots You'll Fall In Love With

Hunter's waterproof glossy black Chelsea boots will seamlessly take you from day to night and ensure you won't have to obsessively check the weather every hour.

Come for the durability of Frye's vintage Italian leather booties, stay for the gorgeous redwood color they come in that will stand out from the rest of your Chelsea boot collection.

Expect to receive plenty of compliments whenever you throw on Koio's bestselling Chelsea boots, which will instantly become a part of your capsule wardrobe.

Best paired with a midi skirt and cozy sweater or a beautiful dress, Khaite's calgary leather Chelsea boots with two-inch heels are made to wear year-round.

If you still want to look cute while doing outdoorsy activities, throw on Timberland's Chelsea boots, which are available in seven (!) different colors.

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 suede of these tan Chelsea boots will 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.

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. These Tory Burch ivory Chelsea boots will 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 a pair 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.

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.

Want added height without a heel? These boots by Diemme should do the trick. The sturdy sole will give you enough support for all-weather wear while adding on a few extra centimeters.

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 we all need it.

I can't say enough great things about Marc Fisher's pointy-toe Chelsea boots. They're insanely comfortable and look great when you're heading to those post-work drinks straight from the office.

Crafted from supple leather, this boot will mold to your foot, making it ideal for weekend looks but chic enough to pair with workwear too.