15 Chelsea Boots That Make Winter Outfits Effortless

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If I had to guess how many times per week I reach for my best Chelsea boots, I’d say at least five. I can't help but let my winter outfits revolve around these sleek black shoes. Time and again, they've gotten me through every type of occasion—particularly when it's cold and getting dressed feels like more of a challenge.

Whether I’m heading out for a casual day of press appointments or meeting up with my girls at our favorite wine bar, I can depend on the best Chelsea boots to take me from one event to the next effortlessly. During the day, you’ll find me wearing my precious shoes with a pair of jeans, a fitted turtleneck, and my go-to trench coat. By night, I’ll transform my look with a satin slip skirt, a chunky knit sweater, and a lengthy wool coat.

Fashion experts agree that these boots are more versatile than others. “Chelsea boots are wardrobe building blocks because they’re versatile and timeless,” says Joni Pangsaeng, senior director of design and merchandising at Reformation. Take a moment to look back through fashion history, and you’ll notice that Chelsea boots have proven their tenacity over decades. It all comes down to their inherently uncomplicated design, according to Nordstrom women's fashion director Rickie De Sole. “It’s an iconic shoe that’s easy to wear thanks to its slip-on-and-off functionality."

Shop the 15 best women's Chelsea boots that will pull together any look with ease, all winter long, ahead.

Chelsea Boot

If you’re going to splurge on Chelsea boots, De Sole recommends this pair from Prada, which can easily be dressed up or down. “They look just as good peeking out from the bottom of a romantic skirt as they do accompanying a high-rise straight leg jean,” the fashion director says.

What reviewers are saying: “Such beautiful boots! Can style in many ways. Pricey but worth it!”

Sizes: 5-10

Color: Black

Material: Leather, rubber

Original Waterproof Chelsea Rain Boot

For drizzly days, you’ll want to slip into this pair of Hunter boots, which fuses the functionality of a rain boot and the style of a Chelsea boot. Their natural latex rubber will keep you completely dry through the strongest showers.

What reviewers are saying: “These are perfect for keeping your feet dry as the weather turns wetter and colder.”

Sizes: 5-11

Colors: Red, green, black

Material: Rubber

Katerina Lug Sole Chelsea Boot

“The Katerina is one of my absolute favorites and a style that has been in the collection since we first launched boots,” says Pangsaeng. It’s not surprising that these sleek boots have remained a steady design in Reformation’s boot collection. The sensible silhouette and durable construction keeps them relevant year after year.

Sizes: 5-11

Color: Black

Material: Leather

Suede Chelsea boots

These Tod's Chelsea boots might be made of supple suede, but that doesn’t mean they’ll lose their sturdy shape over time. Thanks to the leather backing on these boots, they’ll last for years to come.

Sizes: 34-42

Colors: Black, brown

Material: Suede, leather

Laguna Waterproof Lug Sole Chelsea Boot

One of the best ways to upgrade your collection of statement accessories is to invest in a pair of ivory-colored shoes. Sam Edelman’s Chelsea boots will draw the perfect amount of attention to your outfit without overwhelming your look.

What reviewers are saying: “Love these shoes! They fit true to size and are so comfy, I can wear them all day. They go with everything and are so cute! Definitely recommend!”

Sizes: 5-12

Colors: Ivory, black, brown

Material: Leather

Banana Chelsea Boot

Not all Chelsea boots are low to the ground. With a 3 inch heel, this pair from Tory Burch is a departure from the typical Chelsea design. If you’re concerned about comfort, don't stress. These shoes are made with a chunky block heel and a cozy leather sole for extra support.

What reviewers are saying: “I’m always on the hunt for a classic comfortable and versatile bootie and these checked all the boxes!”

Sizes: 5-11

Colors: Black, brown, multicolored

Material: Leather, textile, rubber

Leather Chelsea Boots

If you peer into my closet, you’ll immediately discover shades of caramel, chestnut, and my personal favorite, chocolate. I’ve always believed that brown fits perfectly into any winter color palette, so good luck trying to convince me that I don’t need Gianvito Rossi’s leather boots this season.

Sizes: 36-41

Colors: Brown

Material: Leather

Viv Rangers Buckled Leather Chelsea Boots

An oversized buckle adds some glamour to a shoe that otherwise conforms to Chelsea boot standards. There’s absolutely nothing wrong with keeping it simple— trust me, minimalism is the foundation of my wardrobe— but sometimes it doesn’t hurt to spice things up a bit. Gold hardware will always do the trick.

Sizes: 35-42

Color: Black

Material: Leather

Chelata 30 Leather Chelsea Boots

Manolo is widely known for their high-heeled satin pumps (thank you, Carrie Bradshaw), but their low-heeled shoes are just as fantastic. If you despise the idea of walking around in stilettos, let us introduce you to Manolo’s Chelsea boots— your new go-to shoe.

Sizes: 34-43

Color: Black

Material: Leather

Hobbes Ribbed Cashmere-Trimmed Leather Chelsea Boots

We often think of wearing cashmere in the form of a sweater or scarf, but this soft fabric can also be worn on our feet. Gabriela Hearst’s “Hobbes” shoes aren’t the first pair of cashmere-trimmed boots that I’ve seen, and they certainly won’t be the last. They're that warm.

Sizes: 36-42

Colors: Beige, black

Material: Leather, cashmere

Patent-Leather Platform Chelsea Boots

Wearing a boot with a heel is the best way to boost your look (literally). For those days when your outfit feels a bit too dull, consider trying on GANNI's Chelsea boots with a 1.5-inch platform.

Sizes: 35-41

Color: Black

Material: Leather, rubber

Beige Zipped Boots

As if fitting into a pair of Chelsea boots couldn’t get any easier, The Row introduced an innovative design which features a front zip fastening. If you’re bundling up with a pair of heavy socks, slipping into these shoes isn't a problem—just ask the dozens of fashion insiders who wear them all winter.

Sizes: 35-42

Color: Beige

Material: Leather, rubber

VLOGO Embellished Leather Chelsea Boots

Subtle styles resonate more with me, but I’ve found ways to experiment with embellished looks. I love the way Valentino’s signature gold hardware shimmers against the polished leather backdrop of these Chelsea boots.

Sizes: 35-41.5

Color: Black

Material: Leather

Beige Lug Sole Boots

If your foot is on the wider end of the spectrum, you’ll want to look for a Chelsea boot that is crafted with elasticized gussets, such as this pair from Proenza Schouler. This feature increases the shoe's flexibility, specifically around the ankle area, to provide a seamless slip-on-and-off experience.

Sizes: 35-41.5

Colors: Beige/ black

Material: Suede, rubber

Winnie Water-Resistant Leather Lug-Sole Chelsea Booties

Veronica Beard's Winnie shoe is a fascinating hybrid between two styles. The stretchy elastic side panels reference the classic features of a Chelsea boot, while the thick rubber sole speaks more to the iconic design of a combat boot.

Sizes: 4-12

Color: Black

Material: Leather, rubber

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