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The 11 Best Chelsea Boots to Add to Your Transitional Wardrobe
With everything from classic silhouettes to chunky options.
Byrdie
TL;DR
Our favorite Chelsea boot is the Thursday Boot Company Duchess Chelsea Boot. The sleek design is incredibly comfy and durable. If you’re looking for a waterproof pair, we recommend Ariat Women’s Wexford Waterproof Boot.
With their iconic silhouette, Chelsea boots are a fall and winter mainstay for practical and trendy dressers. The style—derived from a men’s boot made popular on the streets of London—features lug soles, elastic gussets, and pull tabs that allow wearers to slip them on and go. Many Chelsea boots are designed to withstand rainy weather, so you can wear them in place of bulky rain boots.
“Chelsea boots are the ultimate walking boot in the cool weather months,” says Sarah Pierson, co-founder of shoe brand Margaux. “The fitted ankle shaft holds your foot nicely, the lugged rubber sole can match up against any terrain, and the tapered toe of our Chelsea allows the shoe to be dressed up or down depending on the occasion.”
Whether you’re looking for a classic or want something bolder and modern, we spoke to experts and compiled the best Chelsea boots for women based on materials, comfort, fit, and durability.
Top Picks
Thursday Boots Duchess Chelsea Boot at Amazon$160
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Ariat Wexford Waterproof Chelsea Boot at Amazon$200
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Sorel REVEL RD Waterproof Chelsea Boot at Nordstrom$140$105
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Doc Marten’s 2976 Genix Nappa Reclaimed Leather Chelsea Boots at Dick’s$170
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Free People Essential Chelsea Boot at Freepeople.com
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H&M Chelsea Boots at Hm.com
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Blundstone High-Heeled Boots at Blundstone.com
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Vivaia Square-Toe Ankle Chelsea Boots at Vivaia.com
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Ganni Black Stitch Cleated Low Chelsea Boots at Ganni.com
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Vagabond Kelsey Boots at Vagabond.com
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Best Overall
Thursday Boots Duchess Chelsea Boot
Material: Leather | Size Range: 5-12 | Heel Height: 1.25 inches
If you’re looking to invest in a long-lasting, high-quality boot, it’s hard to beat the gold standard set by Thursday Boot Company. They create boots with superb traction and durability—exactly what you need in a Chelsea boot. Beyond their functionality, these boots are beautifully crafted with luxury leathers and suedes that rival those in the $200-$300 price range. Thanks to the absorbing insole, it’s the kind of boot that forms to your feet over time.
Best Waterproof
Ariat Wexford Waterproof Chelsea Boot
Material: Leather | Size Range: 5.5-11 | Heel Height: 1 inch
Coming from a brand that specializes in equestrian wear, you know these boots mean business. They are a fully waterproof Chelsea boot with dry shield construction. The treaded sole is meant to handle slippery and uneven terrain. Despite the ruggedness, they are chic enough to wear in the city thanks to a range of luxurious leather finishes in olive green, chocolate brown, and burgundy shades.
Best for Outdoors
Sorel REVEL RD Waterproof Chelsea Boot
Material: Leather or suede | Size Range: 5-12 | Heel Height: 2.5 inches
Enter your ultimate rainy day accessory: this waterproof Chelsea boot from Sorel. These elevated boots feature both suede and rubber leather options to stomp around in when it’s wet or snowy, or when it’s sunny—we don’t care—they’re cute enough to slip into when the sun is shining, too. That’s because they’re crafted with rich fall shades and have a chunky design throughout.
Best Slip-Resistant
Doc Marten’s 2976 Genix Nappa Reclaimed Leather Chelsea Boots
Material: Reclaimed leather | Size Range: 5-12 | Heel Height: 1 inch
No boots list feels complete without including a pair of Dr. Martens. This take on their classic Chelsea boot gives a rugged twist that has earned our approval. It’s a slip-proof version made from reclaimed leather that is soft, lightweight, and durable. The signature outsole, tonal elasticated panels for easy wear, and a special edition heel loop showcase that these boots are built to last while reducing waste.
Best Heeled
Free People Essential Chelsea Boot
Material: Leather, rubber | Size Range: 6-11 | Heel Height: 2.5 inches
I see shades of blue—and brown, and chocolate, and bone. Well, whichever colorway you choose, you get a quintessential women’s Chelsea boot. Of course, they include the brand’s bohemian flair; these have a towering shaft and a faded design throughout. Though, the standout design here is that stacked heel that gives you just the right amount of height (2.5 inches to be exact) without feeling like too much for a night out on the town.
Best Budget
H&M Chelsea Boots
Material: Polyurethane | Size Range: 4-11 | Heel Height: 1.5 inches
Sometimes, you need a boot that isn’t going to cost you upwards of $200. An impossible feat these days, we know! That’s why our budget recommendation comes from H&M at $50. What makes these so great is that they look more expensive than they are, and it’s all in the details. They are equipped with an elasticized side panel and loop at the back. These also feature satin linings and insoles, making them super comfortable. Style them in stark black or dark brown to easily pair with all your fall outfits.
Best Block Heel
Blundstone High-Heeled Boots
Material: Knit | Size Range: 5-11 | Heel Height: 2.5 inches
Australian footwear brand Blundstone has been successfully making high-quality boots for centuries. That’s because they’re crafted with premium, water-resistant leather and are completely comfortable. These 3-inch stable block heels focus on all-day wear and versatility, which is why they get our stamp (or stomp?) of approval.
Best for Wide Feet
Vivaia Square-Toe Ankle Chelsea Boots
Material: Knit | Size Range: 5-11 | Heel Height: 2.5 inches
Chelsea boots are known for their narrow silhouette, which may not seem the most comfortable if you have wide feet. But fear not! These square-toed boots from Vivaia are designed with an extra roomy toe box that is 30% larger than average. The boots are also made from a stretchy, upcycled knit that’s more flexible than your standard leather. And the best part, it’s water-repellent. Plus, the brand offers a WalkSole that provides extra shock absorption and two times the arch support. Simply said, this is an extremely comfortable Chelsea boot all around.
Best Platform
Ganni Black Stitch Cleated Low Chelsea Boots
Material: Leather | Size Range: 5-15 | Heel Height: 2 inches
Ganni might have the best Chelsea boots for women when it comes to the chunky platform shoes trend. Their heavy, cleated soles are balanced out by narrowly stitched detailing and smooth leather, making them feel like a focal-point shoe while still being able to slip into just about anything while wearing them.
Best Pointed Toe
Vagabond Kelsey Boots
Material: Leather | Size Range: 5-12 | Heel Height: 1.5 inches
Looking to step up your shoe game? Well, the Kelsey from Vagabond is a spot-on way to do so. It’s reminiscent of a Western boot without too much flair, and the pointed toe adds a discernible difference from the traditional round-toe silhouette. Plus, the 1.5-inch block heel provides elevation without feeling overpowering.
Best Splurge
Margaux Chelsea Boot
Material: Leather or suede | Size Range: 3.5-14, narrow, wide | Heel Height: 1.5 inches
At $425, these Chelsea boots are a splurge, but if you’re willing to make an investment, we think it’s well worth it, considering the quality. They are crafted from beautiful, water-resistant Italian leather. In terms of comfort, they offer 5 millimeters of plush foam padding and slip on and off easily. The lug sole adds traction and a nice platform. We love how the brand offers an extensive size range with the option for narrow or wide sizing.
What to Look for in Chelsea Boots
- Material: Since growing in popularity and becoming a more timeless boot style, Chelsea boots have seen upgrades to their soles and fabrications. “They were originally produced only in leather with a very limited color palette, but can now come in a variety of colors, materials, and textures, depending on trends,” says fashion merchandising professor Maureen Lehto Brewster. When deciding on what material is best for you, consider your desired usage. A rubber option is best for wet environments, while suede and leather tend to be better suited for dressing up (though many on this list are waterproof or water-resistant).
- Silhouette: Elastic gussets on the ankle are a defining factor in the Chelsea boot, but silhouettes can differ based on preference. A pointed, square, or round toe, are all common. A taller silhouette is less expected and offers more protection from the cold.
- Sole: Lug-sole boots have become more popular in recent years, and also offer great grip as well as a lift, which can both come in handy in poor weather conditions. For dressier occasions, consider a boot with a taller heel.
Meet Our Experts
Byrdie interviewed the following experts for this article:
- Sarah Pierson is the co-founder of footwear brand Margaux.
- Candace Molatore is a travel and lifestyle content creator.
- Maureen Lehto Brewster is an assistant professor of fashion merchandising at the University of Maryland Eastern Shore.
Why Trust Byrdie
Byrdie contributor Morgan Sullivan has over half a decade of experience in the beauty and fashion industry, writing for some of the most prominent magazines and websites. In addition to writing about fashion, she frequently covers relationship, wellness, and lifestyle topics.
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