25 Winter Outfits That Make Getting Dressed for the Cold Easy
Below, 25 winter outfit ideas from some favorite street-style stars—to keep you inspired to really get Dressed, all season long.
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Of course, there are plenty of coats, knits, and <anchor>boots</anchor>—the obvious must-haves—but I am leaning into a bit of the unconventional, as well. Leather and other textured fabrics are in no short supply on my checklist, while tailoring and midi skirts have become fashion’s new favorites, and mine too. When all else fails, the best basics with a twist make for easy outfit formulas that are foolproof. Think funky denim, colorful striped sweaters, and structured oversize outerwear that makes layering a breeze.
17 Best Chelsea Boots for Women 2024
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# The 17 Best Chelsea Boots for Fall Sophistication

Say hello to your new staple shoe

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As the cooler weather descends, it’s out with the summer sandals and in with the fall boots. Of course the most versatile of fall boots—and one of our favorites—is the Chelsea boot.

Since 1837, the design has been a mainstay in everyday fashion, truly standing the test of time. While you can opt for a traditional black lug-sole pair, brands are also putting their own spins on the signature style by playing with material, colors, and silhouettes. Just look at Moncler’s weather-proof suede, for example, or Dorothee Schumacher’s western-inspired take.

The best Chelsea boots for women are sleek, sophisticated, and perfectly practical. Joni Pangsaeng, senior director of design and merchandising at Reformation, agrees: “Chelsea boots are wardrobe building blocks because they’re versatile and timeless.” They also are incredibly popular due to their convenience and easy design. Nordstrom’s women’s fashion director Rickie De Sole notes, “It’s an iconic shoe that’s easy to wear, thanks to its slip-on-and-off functionality.” Don them casually for an apple-picking excursion with a sweater and jeans, or dress them up for dinner on the town with a miniskirt and tights. Whichever way you choose to wear them, they are the season’s favorite companion.

If you’re sold on the style, there’s only one thing left to do. Shop the 17 best Chelsea boots for women—for the season ahead and the years to come.

## The Best Chelsea Boots of 2024

### Best Designer Chelsea Boots

### Best Waterproof Chelsea Boots

### Best Everyday Chelsea Boots

Best Designer Chelsea Boots

## Prada 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

Best Waterproof Chelsea Boots

## Hunter Original Waterproof Chelsea Rain Boot

Now 45% Off

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

Best Everyday Chelsea Boots

## Reformation 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

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Best Brown Chelsea Boots

## Gianvito Rossi 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

Best Buckled Chelsea Boots

## Roger Vivier 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

Best Low-Heeled Chelsea Boots

## Manolo Blahnik 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

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Best Cashmere-Trimmed Chelsea Boots

## Gabriela Hearst 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

Best Platform Chelsea Boots

## Ganni 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

Best Chelsea Boots With a Zip Fastening

## The Row 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

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Best Western-Inspired Chelsea Boots

## Dorothee Schumacher Leather Chelsea Boots

Now 30% Off

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

Most Iconic Chelsea Boots

## Stuart Weitzman 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: 3½–13

Colors: Black

Materials: Leather, rubber

Best Suede Chelsea Boots

## Moncler 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

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Best Green Chelsea Boots

## Zadig & Voltaire Ride Chelsea Boots

Now 50% Off

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

Best Durable Chelsea Boots

## Anine Bing 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

Best Ankle Chelsea Boots

## AllSaints 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

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Best Statement Chelsea Boots

## 3.1 Phillip Lim 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

Best Practical Chelsea Boots

## Everlane The Lug Chelsea Boots

Now 20% Off

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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For more than 150 years, Harper’s Bazaar has been the preeminent fashion, beauty, and lifestyle resource for women at every age. We cover what’s new and what’s next in fashion by working with the world’s leading authorities in ready-to-wear, footwear, accessories, and more. Every story we publish has been thoroughly researched and vetted by our team of editors and industry experts.

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Gaby Keiderling is a freelance writer, working on fashion, lifestyle, travel, and sports features.

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## The Edit: Fashion

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