15 Best Chelsea Boots to Add to Your Winter Wardrobe

FTR, I brought my TOMS Dakota boots as my sole pair of shoes for a 10-day Europe trip last winter, and they seriously delivered. They're somehow stylish while also being durable AF, with rubber lug soles for A+ traction, nicely cushioned insoles, unique contrast welt, and faux-fur lining on some of the colorways. Plus, TOMS uses a third of profits help fund mental health resources, so it's a purchase you can feel good about.

• Size range: 5-12 with half sizes
• Material: Leather
• Heel height: 1.75"
• Color options: Black, tarmac olive, taupe, pebble grey, or tan
• Waterproof? No

THE REVIEW: "I never leave reviews, but these shoes deserve one!" notes one reviewer. "They are warm, comfy, and I get so many compliments. Super cute with all the function of a solid winter boot for moving around the city."

Real talk: When I wear my Everlane Puffa Boots, I feel powerful as hell. The clog-like heel offers SO much height while feeling surprisingly lightweight, and the unique silhouette will def get you lots of compliments. Plus, Everlane uses leather sourced from a tannery rated gold by the Leather Working Group, which is always a bonus.

• Size range: 5-11 with half sizes
• Material: Leather
• Heel height: 3.25"
• Color options: Black or dark brown
• Waterproof? No

THE REVIEW: As one tester writes, "I love the classic Chelsea style mixed with a clog-like heel, and can’t believe how light these boots are. I’ll definitely wear these daily through fall and winter."

Yep, ofc I had to include a pair of Docs. Featuring the iconic branded pull-tab, chunky outsole, and contrast-stitch Goodyear welt, these bbs are made to last, and they'll score ya major style points, too. Oh, and the leather has a high degree of water resistance, so you don't have to worry when you get caught in a drizzle.

• Size range: 5-12
• Material: Leather
• Heel height: 1.25"
• Color options: Black or dark brown
• Waterproof? No

THE REVIEW: "I have often heard that Dr. Martens need to be 'broken in' before they feel comfortable, but these were super comfortable right out of the box," one review reads. "The sole is very supportive and bouncy, making your steps soft and silent. I wear these to the office, construction sites, music festivals, outdoors, and everything in between."

Are they cheap? Lol, no. But these stunners are well worth the investment, trust. Made with an Italian calf or suede upper, these tall Chelsea boots are the epitome of luxury with their supple kidskin lining, plush insoles, and chic squared toes. Plus, those two-inch stacked heels really ~elevate~ the lewk.

• Size range: 6-10.5 with half sizes
• Material: Leather or suede
• Heel height: 2"
• Color options: Black, cream, or chestnut
• Waterproof? No

THE REVIEW: "Easily the most comfortable heels I own," one reviewer notes. "They are perfect for walking around in the city."

If you're not into the stiff feel of traditional Chelsea boots, these cuties will change your mind. Rather than leather, these water-resistant boots are made with a blend of merino wool and Rothy's signature thread (aka plastic bottles), so they're both sustainable and durable. Reviewers also <3 the flexible knit uppers, the sturdy lug outsoles, and the cloud-like insoles.

• Size range: 5-13 with half sizes
• Materials: Merino wool and recycled plastic bottles
• Heel height: 1.5"
• Color options: Onyx black, graphite brown, dove, or forest
• Waterproof? No

THE REVIEW: "Rothy’s hit a home run with this boot!" raves one tester. "The boot slips on easily, [is] super comfortable requiring no break-in time, has a sturdy, non-slippery sole, and is very cute. The boot design is sleek and not clunky. so it can be worn with everything. These are going to be my go-to shoes this winter."

With its tall shaft, contrasting gullets, and heavily lugged sole, the All Rounder looks so badass—but luckily, they don't feel (or sound!) nearly as clunky as they look. Testers say these boots are quiet, sleek, and comfy, with slip-proof soles and leather uppers that reeeeeally pop in a sea of black Chelsea boots.

• Size range: 5-11.5 with half sizes
• Material: Leather
• Heel height: 2.2"
• Color options: Bright white, cream, stone beige, tan, or dusty olive
• Waterproof? No

THE REVIEW: "Love my new All Rounder boots," one review reads. "They are super comfortable and the bright white is a stunning color! They are a bit stiff to get on initially but fine after a couple of wears. The height is great for skirts, wide leg jeans and pants and even shorts. They go with everything and look fantastic!"

Found: rain boots that don't actually *look* like rain boots. Rather than just water-resistant, Blondo's Chelsea boots are actually waterproof, since they're protected with an AquaProtect seal, meaning water droplets just roll right off 'em. They'll stand up to stormy weather and look good while doing it, thanks to the thick rubber lug sole and contrast welt.

• Size range: 5-11 with half sizes
• Material: Leather or suede
• Heel height: 2.25"
• Color options: Black, java, sand, olive, navy, or cognac
• Waterproof? Yes

THE REVIEW: "I absolutely love these boots!" one review reads. "They are beyond comfortable, versatile, and waterproof! I absolutely love the color of them, and the suede is top-quality."

Just saying, these Cole Haan booties are the ideal mix of style and function. From the v walkable two-and-a-half-inch wedge heel to the padded sock lining and incredibly cushy footbed, the City Wedge is far superior to your bulky ol' snow boots—oh, and did I mention that the leather (which is gold-rated by the Leather Working Group) is totally waterproof??

• Size range: 5-11 with half sizes
• Material: Leather or suede
• Heel height: 2.5"
• Color options: Black, stone gray, British tan, or Irish coffee
• Waterproof? Yes

THE REVIEW: "Absolutely obsessed with these boots," one tester raves. "They are so comfortable and so stylish. I have gotten so many compliments. They are so light and easy to walk in!"

Again, these shoes aren't cheap, but they're a v worthy splurge. The Clara's incredibly lightweight rubber lug sole gives these moto-inspired baddies a chunky lewk without the weight, and the traction is ideal for all kinds of surfaces. Oh, and M.Gemi shoes are made by hand in small batches with locally-sourced Italian leather or suede, so you know you're getting a premium product.

• Size range: 5-12 with some half sizes
• Material: Leather or suede
• Heel height: 1.8"
• Color options: Black or fossil
• Waterproof? No

THE REVIEW: "I love Chelsea boots, but usually they are too tight on my instep—not the Clara!" one reviewer notes. "They are really sleek and cool, and I wore them out of the box with NO break-in period! Amazing!"

I've never worn shoes as comfortable out of the box as these stunners from Beckett Simonon. Made with LWG gold-rated full-grain calfskin leather with soft Vachetta leather linings, these cuties (which are handcrafted by master artisans in Colombia) look so sleek and feel like butter—especially since they include removable EVA inserts.

• Size range: 6-11 with some half sizes
• Material: Leather
• Heel height: 0.75"
• Color options: Black, dove, toffee, or rosewood
• Waterproof? No

THE REVIEW: "These boots were worth the wait," one review reads. "They are beautifully made. The leather is soft and luxurious, the color is beautiful, and they look great on my foot. They are true to size and comfortable enough to wear all day. This is the 4th pair of shoes I have purchased from Beckett Simonon am happy with every one!"

Think you can't dress up a pair of Chelsea boot? Think again, friends. The Liberty boot is created with leathers sourced from Leather Working Group gold- and silver-rated tanneries, with a fitted silhouette, almond-shaped toes, and just the right amount of heel. Best of all, these bbs feature a triple-layer support and cushion system, as well as removable inserts that will give ya a regular, wide, or narrow fit.

• Size range: 6-13 with some half sizes
• Material: Leather
• Heel height: 2.3"
• Color options: Black or biscuit
• Waterproof? No

THE REVIEW: "As expected from Frankie4, exceptional quality, style and comfort," one tester writes. "Wore all day long and to an evening event on first wear. Love the detail, look, and versatility (to date has included with jeans, skirts, and [an] evening dress). On high rotation. Biggest disappointment is that I purchased them so late in season."

These rugged all-weather boots from Rebecca Allen made Oprah's Favorite Things List for 2023, so do with that information what you will. Made with a rubberized mud guard for braving the elements and a super-soft flannel lining to keep your feet snug, these pretty boots will help you get through the winter in ~style.~

• Size range: 6-11 with half sizes
• Material: Leather
• Heel height: 1.5"
• Color options: Black, cream, or nude
• Waterproof? Yes

THE REVIEW: "Wow! The quality of these boots is stellar!" one reviewer raves. "Got my usual size of 8 and they fit like perfection! Get these now! Your wardrobe will thank you!"

With its square toe and ankle shaft height, the Ryan Pro def doesn't look like your typical Chelsea boot...especially since it features a knit upper made from recycled plastic bottles rather than leather. Reviewers are in love with the roomy toe box, cushy microfiber insoles, and anti-slip rubber outsoles—and here's the cherry on top: These shoes are totally water-repellent.

• Size range: 5-11 with half sizes
• Material: Recycled plastic bottles
• Heel height: 1"
• Color options: 12
• Waterproof? Yes

THE REVIEW: According to one review, "They are so comfortable and so chic, a perfect combination. They are a little tricky for me to get on, but once they’re on, they are fabulous—very easy to walk in, [and] supportive of my knees, joints, and feet without being heavy and clunky-looking. I’m very happy with these."