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When you think of closet essentials, we’d bet a great pair of ankle boots comes to mind fairly quickly. And if they don't, then they should! Ankle boots, namely Chelsea boots, are among the most versatile fashion items one could invest in; they pull together virtually any look, slip on and off easily, and wear well over time.
For a bit of history, the first boots with elasticized gussets date back to 1837, during a time when various styles were trending from technological innovations like sewing machines and vulcanized rubber. Like today's Chelsea boots, these early versions were flat with an ankle-length shaft, made of leather, and featured an elastic gusset at the sides to make them easy to put on and take off, fashion expert Maureen Lehto Brewster tells Byrdie. The style became popular again in the 1950s "but included a higher Cuban heel and tapered toe to complement the slim trousers that became popular during this period." They were called Chelsea boots for their association with the British neighborhood at the epicenter of Swinging London in the '60s.
Since then, fashion's relationship to nostalgia has seen Chelsea boots come in and out of style and vary by their heel height, shape, and fabrication. "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," Lehto Brewster says. And given their versatility, stylish people will vouch for having a quality pair on hand at all times.
With all of that in mind, we’ve used our internet research skills and expertise on brands, shoe materials, and shoe constructions to round up the best Chelsea boots on the market, in a slew of categories. For example, a tall pair with a chunky sole and contrast stitching by KHAITE are among the most eye-catching options you can choose, while Isabel Marant's monochrome black pair offer polished edge. Likewise, an Italian leather pair by Everlane is very classic and will go with practically any outfit. Birkenstock, Dr. Martens, and Hunter all offer rugged pairs that are perfect for enduring a variety of weather conditions.
Meet the Expert
Maureen Lehto Brewster is a fashion expert and Ph.D student at the University of Georgia.
For the full list of the best Chelsea boots for women, read on.
Best Overall: Isabel Marant Castay Leather Chelsea Boots
Isabel Marant’s Castay Leather Chelsea boots are so classic, which means they’re perfect for grounding everything from denim and tailored pants to dresses and skirts in a variety of lengths. While they certainly may seem like a splurge compared to other numbers on this list, we can’t help but see the value in them for their quality and versatility. In terms of construction, they’re made from black leather and set on thick rubber soles with a manageable 1-inch heel. They also have elasticized sides with pull tabs so you can slip them on and off easily.
Colors: Black | Heel Height: 1 inch | Size Range: FR 35-41
Best Value: Dr. Martens Flora Chelsea Boot
The Flora Chelsea Boot by Dr. Martens is by far the best value when it comes to Chelsea boots. They’re made from smooth, glossy leather on a low, opaque sole with no visible construction thread. They’re also no-skid, so they’re perfect to wear in rain or snow when you need to maintain an ultra-polished look.
Colors: Black | Heel Height: Approximately 1 inch | Size Range: US 5-11
Best Budget: Everlane The Italian Leather Chelsea Boot
Everlane's Chelsea boot echoes elegance, timelessness, and great value (they're priced under $200). The upper is made from Italian leather and features a rounded toe and leather pull-tab. For optimum comfort, it has elastic panels both on the sides, and for stability, its soles are made of textured rubber. This will be the everyday leather boot you can wear well from fall to spring, pairing seamlessly with everything from black jeans or knitted flares to a floral midi dress.
Colors: Black, Tobacco, Off-White | Heel Height: Approximately 1 inch | Size Range: US 5-11
Best for Outdoors: Blundstone Thermal Chelsea Boot
Regarded as one of the most durable boot brands, Blundstone introduced its Thermal Series and it's our top recommendation if you need to keep your feet warm, dry, and stylish. Featuring removable shearling footbeds, waterproof leather and seams, and an "ergonomically engineered toe spring," these Chelsea boots have all the perks of purely functional, bulky winter boots—but they also bring some street style cred. Don't be afraid to hit the trails or stomp in some puddles with this pair.
Colors: Black, Antique Brown | Heel Height: 1.5 inches | Size Range: US 5-13
Best Lug Sole: Dr. Martens 2976 Smooth Leather Chelsea Boots
This pair by Dr. Martens offers a rugged and chunky take on the Chelsea style. It comes in the brand’s signature smooth leather and is completed with yellow welt stitching, a heel-loop, and a Goodyear welt, which makes for an extra sturdy sole. Reviewers love the quality but recommend both going up a size and always wearing socks, as this pair takes a while to break in.
Colors: Black Smooth Leather | Heel height: Approximately 1 inch | Size Range: US 5-11
Best Patent: Tod’s Leather Ankle Boots
For maximum shine and a little lift, Tod’s has just the thing. Its Chelsea boots have been crafted in Italy from glossy patent leather and sit on rubber soles with a block heel. Wear them with straight-leg jeans, a knitted midi skirt, or, as NET-A-PORTER suggests, a delicate tea dress.
Colors: Black, Brown, Burgundy | Heel Height: 2.3 inches | Size Range: IT 34-41
Best Vegan: Stella McCartney Trace Chelsea Boot
British designer Stella McCartney is known for her commitment to veganism in fashion, so it’s only natural that we name her Chelsea boots the best in this category. This pair is made in Italy from faux leather and features elastic gussets, jacquard-woven pull tabs with the label’s logo, and thickset rubber soles.
Colors: Black | Heel height: 1.5 inches | Size Range: EU 35-41
Best Pointed Toe: Acne Studios Chelsea Boots
Acne Studios designer Johnny Johansson imbues his made-in-Italy, luxurious shoes with an edge. These leather ankle boots take on the classic Chelsea style in smooth black leather, with a fine gunmetal trim hugging the pointed toe. They’re low-cut, and they have gussets and a back tab to make them easy to pull on and take off.
Colors: Black | Heel height: 1.5 inches | Size Range: EU 35-41
Best Knitted: Chloé Jamie Chelsea Boot
Get cozy in Chloé’s innovative take on Chelsea boots. We love the designer’s use of knitwear to warm up the boot and replace the typical elastic gussets. The lug sole and block heel are equal parts practical and stylish, and overall, the style does a great job of balancing masculine and feminine design features.
Colors: Black, Tannish Brown, Burning Camel | Heel height: 1.3 inches | Size Range: US 4.5-11
Best Weatherproof: Aquatalia Leila Waterproof Leather Boot
Few luxury brands prioritize waterproofing like Aquatalia. The brand prides itself on its ability to marry fashion-forward and distinctly Italian design with quality and comfort. The brand’s Leila style is a great demonstration of these goals and values. It keeps feet dry in wet conditions to add polish and versatility regardless of the weather, which those who live in true four-season climates should very much appreciate.
Colors: Black | Heel height: 1.5 inches | Size Range: US 5-12
Best Eco-Friendly: Ganni Recycled Rubber Chelsea Rain Boot
Chunky lug-soled boots are quite the trend right now, and Ganni makes a pair that’s hard to resist from both a style and sustainability standpoint. It’s made in Portugal from 50 percent recycled rubber in a matte finish and is complete with branded pull tabs and elastic panels. We love them because they work well with virtually everything, adding just the right amount of toughness to delicate dresses, skirts, and other tailored looks and complimenting raw edge denim and T-shirt combos. For extra warmth, score the faux shearling version.
Colors: Black, Kalamata, Madder Brown, Shocking Pink, Spectra Yellow | Heel height: 1.5 inches | Size Range: US 5-11
Best Utilitarian: Birkenstock Stalon Chelsea Boot
Birkenstock is well-known for comfort and support, and the Stalon boot is no exception, reviewers say. Made in Portugal, this Chelsea style has a contoured cork footbed to ensure arch support and a sole designed intentionally for great traction. If you plan to wear socks, wearers say to size up from your normal size with the brand.
Colors: Black Nubuck Leather, Graphite Nubuck Leather | Heel height: 1.25 inches | Size Range: US 5-15.5
Best Tall: KHAITE Calgary Leather Chelsea Boots
KHAITE’S Calgary Leather Chelsea Boots prove that a little height goes a long way when it comes to boots. The taller shaft is a twist on the classic Chelsea boot style that gives the illusion of length at the leg. Plus, the chunky sole with white topstitching is modern and easily paired with a range of outfits.
Colors: Black, White Leather, Dark Brown, Caramel Suede | Heel height: 2.8 inches | Size Range: EU 36-41
What to Look for in A Pair of Chelsea Boots
Most Chelsea boots are made from leather, suede, or rubber—and each has its appeal. Leather is classic, comfortable, and long-lasting, while suede wears much more easily and can be difficult to keep in tip-top shape. (So, if you have a looming fear that your shoes will be ruined after just a few wears, perhaps the best choice for you is dark leather, especially one that has been weatherproofed by the maker. Otherwise, suedes and lighter colored leathers make for great stand-out pieces.) Rubber is very durable but not the most eco-friendly unless it’s made from recycled materials.
Chelsea boots are close-fitting ankle boots, most often made with a rounded toe, low-profile sole, and very low heel. However, many offshoots of the classic Chelsea boot incorporate pointed and square toes, as well as chunkier soles, higher heels, and taller shaft heights.
What Are Chelsea Boots?
Chelsea boots are a class of footwear that is close-fitting to the ankle and easy to pull on and off, thanks to features like elastic gussets and pull tabs. The most classic Chelsea boots are designed with a very low heel and a rounded toe, though some designers push boundaries and incorporate various kinds of constructions and designs.
How Do You Style Chelsea Boots?
Chelsea boots can freshen up many different looks and be styled with anything from knee-length skirts to shorts to leggings and cropped jeans. It all depends on the exact style of the Chelsea boot in question, as well as your taste.
Why Trust Byrdie
Hayley Prokos is a freelance writer and editor focused on fashion and lifestyle. She contributes regularly to Byrdie’s commerce section and has a passion for sourcing chic and practical pieces with long-term wearability. After hours of research, she gathered enough insight to determine which Chelsea boots are worth buying.