17 Chelsea Boots That Make Fall 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 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

Colors: Black

Materials: Leather, rubber

Original Waterproof Chelsea Rain Boot

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

Materials: 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,” Pangsaeng says. It’s not surprising these sleek boots have remained a steady part of Reformation’s boot collection. The sensible silhouette and durable construction keep them relevant year after year.

Sizes: 5–11

Colors: Black

Materials: Leather

Leather Knit Sock Chelsea Booties

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 palette, so good luck trying to convince me I don’t need Gianvito Rossi’s leather boots this season.

Sizes: 6–12

Colors: Moka

Materials: Leather, knit

Viv Rangers Buckled Leather Chelsea Boots

An oversize 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 EU

Colors: Black

Materials: Leather

Chelata 30 Leather Chelsea Boots

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

Sizes: 34–43 EU

Colors: Black

Materials: 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 I’ve seen, and they certainly won’t be the last. They’re that warm.

Sizes: 36–42 EU

Colors: Beige, black

Materials: 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 EU

Colors: Black

Materials: Leather, rubber

Zipped Boot I

As if fitting into a pair of Chelsea boots couldn’t get any easier, the Row introduced an innovative design that features a front zip fastening. If you’re bundling up with a pair of heavy socks, slipping into these shoes is not a problem.

Sizes: 35–42 EU

Colors: Beige

Materials: Leather, rubber

Leather Chelsea Boots

For a less traditional style, consider Dorothee Schumacher’s western boots. A silver pointed toe brings a touch of glamour with each step, and it also serves to elevate the style so that you can wear it for fancier occasions.

Sizes: 6–12

Colors: Black

Materials: Leather

5050 Soho Booties

Stuart Weitzman is the master of all things boots. Keep this pair in your closet, as it’s a wardrobe staple that isn’t going anywhere any time soon. The timeless black leather and lug-sole design make it timelessly functional.

What reviewers are saying: “These boots have become my go-to! I’m so happy I purchased them. The leather is so soft and is so comfortable.”

Sizes: 3?–13

Colors: Black

Materials: Leather, rubber

Hevea Chelsea Boots

Moncler makes some of my personal favorites. The soft suede contrasts with the hefty lug sole for a style that is as chic as it is durable. Wear this pair on a hike, at aprés ski, or as you galavant around the city.

Sizes: 36–41 EU

Colors: Tan

Materials: Suede

Ride Chelsea Boots

Instead of the predictable (yet iconic) black or a demure brown, you can mix it up and opt for a hunter green. It’s a color that is still neutral enough for easy styling, while adding vibrance to any fit.

Sizes: 36–41 EU

Colors: Military, black, ice, and more

Materials: Leather

Justine Boots

These boots are going to be relevant for years and years to come. While they retain a standard Chelsea boot silhouette, Anine Bing’s careful craftsmanship ensures these will last. The chunky sole also gives a little boost of height.

Sizes: 6–11

Colors: Black

Materials: Leather, rubber

Ada Leather Ankle Boots

Not all Chelsea boots have a tall shaft. This ankle boot, for example, brings the classic look into a less restricted fit. Pull tabs at the front and back make for convenient wear.

Sizes: 6–11

Colors: Black

Materials: Leather

Downtown Western Chelsea Booties

Another western-inspired pair of Chelsea boots for those that prefer the aesthetic. This pair is more overt in its silhouette, with a curved toe, slanted block heel, and pleated sides.

Sizes: 6–11

Colors: Black

Materials: Leather

The Lug Chelsea Boots

Everlane’s Chelsea boots are ideal for everyday wear. The boots are also treated with a water-resistant spray, protecting the leather from a drizzle or flurry.

What reviewers are saying: “This is the most amazing boot I own. It is comfortable, practical and fabulous looking. It can go with absolutely anything.”

Sizes: 5–11

Colors: Black, bordeaux, beech, and more

Materials: Leather

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