• What’s notable: This boot is constructed of soft suede leather with an ergonomic footbed
• What could be better: Lighter colors are prone to staining

Astorflex isn’t your average boot brand. The same family has been handcrafting leather shoes in Northern Italy for six generations and their Bitflex Chelsea is seriously comfortable and stylish. “I like how this pair strikes the right balance between rugged and refined,” say Forbes Vetted senior editor Kari Molvar. “It’s extremely well made and the price is actually quite reasonable, given the level of construction.” With a soft, European suede—or leather—upper, an ergonomic footbed complete with crepe rubber soles for cloud-like comfort and five easy-to-wear colorways, this boot is our top pick.

Sizes: 7 to 15 | Colors: 5 total, including Tobacco and Dark Chestnut Nubuck | Materials: Leather, crepe rubber | Waterproof: No | Positive reviews say: These boots are the “perfect blend of classic and modern. They go with everything in my wardrobe.” | Negative reviews say: The “suede uppers and crepe sole are not water-resistant.”

• What’s notable: Vegan leather upper is crease-resistant
• What could be better: Runs large; consider sizing down

Bruno Marc gets a lot of style points with this boot: The classic design complements just about any outfit, it comes in both suede and smooth vegan leather finishes and the price can’t be beat. “While more expensive boots typically feature higher grade leather and better stitching, not everyone has a couple hundreds to shell out for boots,” says Molvar. “This pair is a smart compromise.” An EVA foam insole makes these comfortable right out of the box and the rubber-like outsole offers extra traction.

Sizes: 6.5 to 15 | Colors: 8 total, including Black and Tan | Materials: Vegan leather, TPR (thermoplastic rubber) | Waterproof: Water-resistant | Positive reviews say: These “boots are surprisingly comfortable, especially for the price” and have a classic Chelsea look that’s easy to dress up or down.” | Negative reviews say: The “sole is a bit thin and offers limited cushioning.”

• What’s notable: Leather lining and cork insoles mold to your feet for a great fit
• What could be better: Only available in two colors

Handmade in Port Washington, Wisconsin, Allen Edmonds’ Chelsea boot is both versatile and built to last. It’s made using a bench welt construction process that attaches the leather upper to the sole, plus a hot-cork injected insole molds to the shape of your foot over time for a custom—and comfortable—fit. If your boots ever wear out, Allen Edmonds also has a recrafting service, offering resoling, repairs and more. “The higher price point is justified by the way these boots are made, by hand and with attention to detail,” says Molvar. “This is a pair you’ll keep for years.”

Sizes: 7 to 14, D and EEE widths | Colors: 2 total, including Snuff and Whiskey | Materials: Leather, rubber | Waterproof: Weatherproof | Positive reviews say: The “soles feel like sneakers” and “have excellent traction and just the right amount of softness.” | Negative reviews say: “This leather is porous” and “the backs of the boots are a little loose.”

• What’s notable: Oiled leather upper, cushioned footbed and slip-resistant outsole
• What could be better: Unlined so might not be warm enough for extreme cold

American brand Danner may be best known for their outdoor gear, but the durable Bull Run Chelsea boasts some impressive features for a work boot: there’s a non-marking rubber outsole that’s oil- and slip-resistant, a cushioned footbed for all-day comfort, and a steel shank for added support. “Danner is my go-to brand for rugged boots that can take a beating and still look good,” says Molvar. The oiled leather upper—which is rated by the Leather Working Group (LWG)—is resistant to water and other spills on the job and the handcrafted stitching adds strength to the construction, ensuring these will last for years to come. Note: these boots meet ASTM electrical hazard standards, too.

Sizes: 7.5 to 15, D and EE widths | Colors: 2 total, including Black and Brown | Materials: Leather, rubber | Waterproof: Water-resistant | Positive reviews say: “The leather is of good quality. The soles are sturdy.” | Negative reviews say: “They’re “snug at first, especially around the top arch of the foot” but they break in well after a few weeks.

• What’s notable: Responsive cushioning absorbs impact of each step you take
• What could be better: Some reviewers noticed inaccurate colors

Cole Haan marries luxurious style and rugged utility with the versatile, wear-anywhere Zerøgrand Chelsea Boot. The waterproof leather upper has sealed seams to keep the rain out while the EVA outsole is lightweight and flexible without weighing you down. “I’d recommend this pair if you’re commuting or traveling,” says Molvar. “It’s best for light showers, not a heavy downpour—for that, you need actual rain boots.” A fully padded leather lining and cushiony foam footbed add to the all-day comfort, making these a good choice for work, travel or dinner.

Sizes: 6.5 to 16, Medium and Wide widths | Colors: 3 total, including Bourbon Leather and Black-Dark Pavement | Materials: Leather, EVA | Waterproof: Yes | Positive reviews say: “This is my third pair of the exact same boot. They are comfortable, love the styling and a great plus is that they are waterproof.” | Negative reviews say: “The shoe was entirely too narrow” and “they started stretching after a few wears.”

• What’s notable: Heat-activated memory foam insole molds to your foot with each wear
• What could be better: Some break-in time is required, as is the case with most leathers

“We’ve tested Amberjack boots at Forbes Vetted and been impressed with the quality,” says Molvar. Their Chelsea has the durability of a hiking boot, the movement of an athletic sneaker and an A-grade full grain leather upper. With smooth lines that create a slim, elongated look and a dual-action outsole that offers both flexibility and support, this boot keeps you comfortable for the long haul. If your feet tend to overheat in boots, the soft sheepskin lining has tiny perforations to encourage air flow and keep you cool.

Sizes: 7 to 13 | Colors: 9 total, including Chestnut and Onyx | Materials: Leather, TPU | Waterproof: No | Positive reviews say: These boots are “comfortable right out of the box and get better with wear.” | Negative reviews say: “The left boot was overly tight” and some people experienced shipping delays.

• What’s notable: Insulted for warmth and Vibram all-terrain soles for icy conditions
• What could be better: On the expensive end

“No list of Chelsea boots is complete without Blundstones,” says Molvar. The Australian brand is famous for their pull-on Chelsea styles and this unisex winterized version doesn’t disappoint: The Thinsulate lining provides bulk-free warmth, a durable Vibram sole offers high traction and the rounded toe allows for breathing room without feeling compressed. With a waterproof leather upper, you’ll be fully protected from cold, snow and rain. Sizing note: they run true to size but the brand recommends sizing up a half size for wide feet.

Sizes: 4 to 14 | Colors: 3 total, including Antique Brown and Black | Materials: Leather, rubber | Waterproof: Yes| Positive reviews say: The boots are “supremely comfortable, and very warm,” and they performed “great in snow and ice.” Negative reviews say: “The seams on the inside of the heel are very rough and gave me instant blisters” and one reviewer had sizing issues, so check the size chart before ordering.  

• What’s notable: Impeccable leather construction for durability
• What could be better: No wide sizes available

“Beckett Simonon boots come highly recommended by a Forbes staffer who has a pair and can’t say enough good things about it,” says Molvar. “In particular the fit and comfort is truly next level.” Thanks to supple leather inside and out plus an ethical, made-to-order handmade process that fits your foot exactly, the brand’s Bolton Chelsea are some of the highest quality boots out there. Impressive design details include a shea butter-conditioned leather upper that gets a patina with age, a leather lining that regulates temperature and an almond-shaped toe box and elongated shaft that creates a lean silhouette for easy styling. The company also has a Gold rating by the Leather Working Group (LWG), meaning their tannery has some of the best environmental practices in the industry.

Sizes: 7 to 14 | Colors: 4 total, including Black and Bordeaux | Materials: Leather, rubber | Waterproof: No | Positive reviews say: These boots “fit like a glove” and the quality is top-notch and “worth the price.” | Negative reviews say: “I was hoping for more cushion support,” and “they get scuffed up rather easily.”

• What’s notable: The company will resole and reheel these boots if they wear out
• What could be better: Leather requires maintenance to keep it in good shape

New York City-based Thursday Boots prides themselves on quality leather boots at reasonable prices. With options in leather or weather-resistant suede, the versatile Cavalier can be dressed up with a suit or dressed down with jeans. The leather breaks in nicely and the cork midsoles are designed to form to your foot’s shape with wear. Thanks to Goodyear welt rubber outsoles, this boot is durable and can also be easily resoled when the time comes.

Sizes: 6 to 14 | Colors: 6 total, including Sandstone and Dark Brown Suede | Materials: Rubber, leather | Waterproof: Water-resistant | Positive reviews say: These boots “seriously comfortable without needing much of a break-in period.” The recommendation to go a half-size down is “spot-on” and gives you “a perfect fit with a thin sock.” | Negative reviews say: There are “lots of scratches and blemishes on the suede.”

• What’s notable: Affordable price and comfortable for everyday wear
• What could be better: Some reviewers reported the bottom sole came loose after repeated wear

The Rockland took the classic Chelsea silhouette and added a modern twist: the contrast stitching makes a fashion statement, the shorter shaft is more versatile for dressier looks and the crepe-like rubber sole adds grippy comfort. A soft fabric lining helps keep you feet cool by wicking away moisture and the removeable memory foam insole makes these ultra-comfortable for both dressy and casual events.

Sizes: 8 to 16, medium and wide widths | Colors: 6 total, including Black and Redwood Smooth | Materials: Vegan leather, rubber | Waterproof: No | Positive reviews say: There’s “nothing to dislike” about this pair and reviewers “love the color, the style,” calling them the “best fitting dressy shoes I’ve bought in a while.” | Negative reviews say: The fit is a little big, while “the upper material chips easily” and there’s “zero arch support.”

• What’s notable: More lightweight than other Chelsea boots
• What could be better: Mesh lining might rub the ankle

Johnston & Murphy knows a thing or two about high-quality leather shoes; they’ve been making them since 1850. Their sleek Upton Chelsea Boot has an oiled full-grain leather upper, a memory foam sole for extra cushioned comfort and an anti-microbial mesh lining that keeps your feet fresh. Expect these to be wearable right out of the box: multiple reviewers said no break-in time is required.

Sizes: 8 to 14 | Colors: 2 total, including Tan Full Grain, Brown Oiled Full Grain | Materials: Leather, rubber | Waterproof: No | Positive reviews say: This boot is “comfortable with plenty of cushioning” and lightweight. | Negative reviews say: The fit is “narrow toward the toe” and “too stiff for me.”

Part of their “Lost Archives” collection, this pull-on-style Dr. Martens is made with a lightly textured, durable leather that has a soft sheen. It’s finished with elastic gussets and the classic details you’d expect, including the iconic stitching, grooved sides and comfortable air-cushioned soles.

For a distressed take on the Chelsea boot, the 2976 Chelsea is made with naturally broken-in Crazy Horse leather, a heel loop at the back and a cushioned sole that’s oil and fat resistant, with slip resistance. This pair has a unisex fit, so it comes in sizes for both men and women.