The Best Boots for Men, Rated for Comfort, Style and Weather

The best boots for men are the ones you can wear on a cold commute, a muddy weekend, and a dinner date without a second thought. We pulled twenty pairs from brands you know, including Red Wing, Thursday, Blundstone, Clarks, and Danner, and sorted them by what each one does best. You will find Chelsea boots, chukkas, service boots, moc toes, work boots, a cowboy boot, and real snow boots.

Every pick gets four scores out of five, for comfort, walkability, dress up range, and weather. Each boot also comes with a short note on who should skip it, plus outfit ideas so you know what to wear with it. Start with the Thursday Captain at the top if you only want one pair, then work down the list for dress boots, rain boots, and winter gear.

Best overall men's boot

1. Thursday Boots Captain Lace-Up Boot in Brown

Comfort

4/5

Walkability

4/5

Dresses up

4/5

Weather ready

3/5

Thursday's Captain is a classic lace-up service boot in brown chrome leather, built on a Goodyear welt so it can last for years. Inside you get a glove leather lining, Poron shock absorbing insoles, and a cork bed midsole that forms to your feet. A studded rubber outsole, waxed cotton laces, and a choice of standard or wide widths make it the easiest boot on this list to recommend to almost any guy.

Wear the Captain with dark selvedge jeans, a gray crewneck sweater, and a waxed jacket for a simple fall uniform. It also dresses up nicely with chinos, an oxford shirt, and a navy blazer. When you want something rougher for the weekend, the dark brown Thursday Explorer brings the same build with a chunkier sole.

Skip it if: Skip it if you want a boot that slips on and off without any laces.

Shop it at Thursday Boots

Best everyday Chelsea boot

2. Blundstone Original 500 Chelsea Boot in Stout Brown

Comfort

4/5

Walkability

5/5

Dresses up

2/5

Weather ready

4/5

Pull on the Original 500 once and you will see why Blundstone has kept the design going since 1969. The stout brown leather is water resistant and unlined, and XRD Technology in the heel absorbs up to 90 percent of walking impact. Add a TPU outsole, a cushioned midsole, and a steel shank, and you have a boot for errands, travel, and muddy paths alike.

Pair the 500 with straight jeans, a flannel shirt, and a quilted vest for easy weekends. It looks just as right with olive chinos and a chunky crewneck. For colder and wetter months, the black Blundstone Thermal 566 keeps the same shape and adds insulation.

Skip it if: Skip it if you want a soft boot right away, since the thicker leather has a firmer fit that takes time to wear in.

Shop it at Blundstone

Best heritage investment boot

3. Red Wing Iron Ranger 6-Inch Boot in Amber Harness

Comfort

3/5

Walkability

4/5

Dresses up

3/5

Weather ready

3/5

Red Wing first built the Iron Ranger for iron miners in the 1930s, and the toe cap and steel speed hooks still give it away. Amber Harness is a heavyweight oiled and waxed leather with visible natural marks, set on a Goodyear leather welt and a Vibram mini lug outsole. Leather insoles and a cork midsole form to your feet over time, so the fit gets more personal the longer you wear them.

Wear the Iron Ranger with raw denim cuffed once, a white tee, and a chore coat. It also works with heavy wool trousers and a shawl collar cardigan in winter. For a softer laced option on lighter days, the beeswax Clarks Desert Boot is an easy partner.

Skip it if: Skip it if you want a light, flexible boot, since the heavyweight leather needs time to mold to your foot.

Shop it at Red Wing

Best desert boot

4. Clarks Desert Boot in Beeswax Leather

Comfort

4/5

Walkability

4/5

Dresses up

3/5

Weather ready

2/5

Clarks introduced the Desert Boot in 1950, and this version swaps the usual suede for premium beeswax leather. Its traditional stitch down construction molds to your foot over time, and it sits on the signature natural pebble crepe sole. With a leather lining and a simple lace fastening, it is the most low key boot on this list and the easiest to wear on mild fall days.

Wear it with slim chinos, an oxford shirt, and a navy cardigan. It also pairs well with light wash jeans and a field jacket. For a dressier take at the same ankle height, try the dark brown suede Thursday Cavalier.

Skip it if: Skip it on slushy days, since crepe soles and wet streets do not get along.

Shop it at Clarks

Best suede Chelsea boot

5. Thursday Boots Cavalier Chelsea Boot in Dark Brown Suede

Comfort

4/5

Walkability

3/5

Dresses up

4/5

Weather ready

2/5

Dark brown WeatherSafe suede and flexible elastic goring make the Cavalier a Chelsea boot you can pull on in seconds. It has a Goodyear welt, a glove leather lining, and a cork bed midsole over shock absorbing insoles. A leather outsole with TPU studs adds some grip without losing the slim, dressy profile.

Wear the Cavalier with charcoal wool trousers, a black turtleneck, and an overcoat for dinner plans. It also looks sharp with dark jeans and a suede trucker jacket. If you want a leather Chelsea that shrugs off rain, the British Tan Cole Haan ZeroGrand is the one to grab.

Skip it if: Skip it if you walk a lot on wet pavement, since the sole is leather.

Shop it at Thursday Boots

Best moc toe boot

6. Red Wing Classic Moc 6-Inch Boot in Oro Legacy

Comfort

4/5

Walkability

4/5

Dresses up

2/5

Weather ready

3/5

For over 70 years, the Classic Moc has been the boot most people picture when they hear Red Wing. Oro Legacy leather is oiled with a blend exclusive to the brand and keeps its full grain texture with no added pigment, while Puritan triple stitching outlines the moc toe. A Traction Tred wedge sole and a last with extra room in the forefoot and instep make it a comfortable pick for long days on your feet.

Pair the moc toe with faded jeans, a heavy flannel, and a canvas work jacket. It also looks good with olive cargo pants and a gray hoodie on weekends. Keep it next to the Amber Harness Red Wing Iron Ranger and you have the brand's two most famous boots covered.

Skip it if: Skip it if you need a boot for the office, since the light wedge sole reads very casual.

Shop it at Red Wing

Best dress boot

7. Allen Edmonds Park Boot in Black

Comfort

3/5

Walkability

3/5

Dresses up

5/5

Weather ready

2/5

Allen Edmonds built the Park Boot for business, with a sleek, polished black leather upper and a classic cap toe. It is lined in leather with a leather insole, and a stacked 1 inch heel sits on a leather and rubber outsole. It also comes in a range of widths, which matters a lot in a dress boot.

Wear it with a charcoal suit and a white shirt when you want something sharper than an oxford in winter. It also lifts gray flannel trousers and a navy sweater for a smart casual office. For a less formal black lace-up, the Wolverine 1000 Mile shows a little more stitching and character.

Skip it if: Skip it if you mostly wear jeans and sneakers, since this one looks best with tailoring.

Shop it at Zappos

Best sleek leather lace-up

8. Wolverine 1000 Mile Plain-Toe Classic Boot in Black Leather

Comfort

3/5

Walkability

3/5

Dresses up

4/5

Weather ready

2/5

Wolverine recreated the 1000 Mile from its archival 1914 pattern and still makes it by hand in the USA. The unlined upper is premium Horween leather, and the Goodyear welt means a cobbler can resole it for years. A leather outsole with a Vibram rubber forepart and heel adds traction to a slim shape that looks closer to a dress boot than a work boot.

Wear the black 1000 Mile with black jeans, a merino crewneck, and a gray overcoat. It also pairs well with slim navy chinos and a denim shirt. If you prefer brown, the Amber Harness Red Wing Iron Ranger has the same heritage feel with a rounder toe.

Skip it if: Skip it if you want a soft, padded feel, since the upper is unlined.

Shop it at Wolverine

Best waterproof dress Chelsea

9. Cole Haan ZeroGrand Remastered Waterproof Chelsea Boot in British Tan

Comfort

4/5

Walkability

4/5

Dresses up

3/5

Weather ready

5/5

Cole Haan's ZeroGrand Remastered Chelsea has a waterproof British Tan leather upper with sealed seams, so a rainy commute will not ruin it. Underneath you get a foam footbed and a FlowerFoam midsole made with at least 25 percent natural dandelion rubber. Elastic gores keep it easy to pull on, and the ZeroGrand outsole gives it a sportier base than a classic Chelsea.

Wear it with navy chinos, a white oxford, and a trench coat on wet workdays. It also looks great with dark jeans and a camel crewneck. On dry evenings, the dark brown suede Thursday Cavalier is the dressier Chelsea to trade in.

Skip it if: Skip it if you want a traditional leather sole, since this one sits on a sporty foam outsole.

Shop it at Cole Haan

Best side zip boot

10. Frye Paul Inside Zip Boot in Brown

Comfort

3/5

Walkability

4/5

Dresses up

4/5

Weather ready

2/5

An interior side zipper gives Frye's Paul the clean look of a pull-on boot without the wrestling match. It is made of oiled leather with a leather lining, a cushioned insole, and a round toe on a 5 inch shaft. A Goodyear welt and a traction rubber outsole make it sturdier than most zip boots.

Pair the Paul with tailored gray trousers and a navy knit polo for an office that leans casual. It also looks good with straight dark jeans and a brown leather jacket. If you like Frye leather but want more attitude, the black Frye Harness 8R is the rugged option.

Skip it if: Skip it if you like to fine tune the fit with laces, since the zipper is the only closure.

Shop it at Frye

Best western boot

11. Tecovas The Cartwright Cowboy Boot in Scotch Goat

Comfort

4/5

Walkability

2/5

Dresses up

3/5

Weather ready

1/5

Tecovas built the Cartwright as a classic cowboy boot with a round toe, a 1.5 inch stacked angled heel, and a 12 inch shaft with hand laid cording. This pair comes in Scotch goat leather, which the brand says breaks in quickly and develops a patina fast. A 3/4 Goodyear welt, a cowhide lining, a tri-layer insole, and reinforced pull straps round out the build.

Wear the Cartwright with straight jeans that stack over the shaft, a pearl snap shirt, and a denim jacket. It also works for an outdoor wedding with a tan suit and an open collar. Keep the rest of the outfit simple so the warm brown leather stands out.

Skip it if: Skip it if you need grip on wet or icy streets, since the sole is leather.

Shop it at Tecovas

Best combat boot

12. Dr. Martens 1460 Smooth Leather Lace Up Boots in Black Smooth

Comfort

3/5

Walkability

4/5

Dresses up

2/5

Weather ready

3/5

Doc Martens fans know the 1460 by its yellow stitching, eight eyelets, and AirWair heel loop. It is Goodyear welted with the classic Z welt stitch, lined in textile, and fitted with a cushioned footbed. The air cushioned rubber sole resists oil and slipping, and the 6 inch shaft sits just above the ankle.

Wear the Docs with black slim jeans, a band tee, and a leather jacket for the classic look. They also toughen up gray chinos and a plaid overshirt. For a brown lace-up with a similar presence, the Rocky Road Thursday Explorer is a more grown up alternative.

Skip it if: Skip it if your workplace has a formal dress code.

Shop it at Zappos

Best lug sole boot

13. Thursday Boots Explorer Combat Boot in Rocky Road

Comfort

4/5

Walkability

4/5

Dresses up

2/5

Weather ready

3/5

Built on a chunky Vibram Newflex outsole, the Explorer is Thursday's tall combat boot in Rocky Road leather. A storm welt, a padded collar, and memory foam insoles add toughness and comfort, while a steel shank and cork bed midsole keep it supportive. Kevlar blend laces and a glove leather lining finish a boot built for hard wear.

Wear it with dark jeans, a cable knit sweater, and an army green field jacket. It also looks great with wool cargo pants and a black puffer in deep winter. For real snow, though, step up to the buff Sorel Caribou.

Skip it if: Skip it if you want a low, sleek boot, since the shaft runs tall.

Shop it at Thursday Boots

Best waterproof weekend boot

14. Cole Haan American Classics Waterproof Plain Toe Boot in Irish Coffee

Comfort

4/5

Walkability

5/5

Dresses up

2/5

Weather ready

5/5

Rain and mud are no problem for the American Classics Waterproof Plain Toe Boot, which Cole Haan makes with waterproof leather and sealed seams. The upper is suede, the footbed is cushioned with arch support, and a storm bead welt adds a heritage touch. Its EVA outsole has a rugged lug tread with rubber pods at the forefoot and heel for grip on slick ground.

Wear it with relaxed chinos, a fleece pullover, and a rain shell for wet weekends. It also works with dark jeans and a barn coat on a rainy trip out of town. For drier days with a similar laced look, the brown Thursday Captain is more polished.

Skip it if: Skip it if you are between sizes, since Cole Haan says this style runs large.

Shop it at Cole Haan

Best hiking style boot

15. Danner Mountain Light in Brown

Comfort

3/5

Walkability

5/5

Dresses up

1/5

Weather ready

5/5

Danner introduced the Mountain Light in 1979, and it is still built by hand in Portland, Oregon. A one piece full grain leather upper and a waterproof GORE-TEX liner keep water out while letting sweat escape. The Vibram Kletterlift outsole grips on wet and dry ground, and the stitchdown build means Danner can recraft it later.

Wear the Mountain Light with wool socks, cuffed jeans, and a fleece for a fall hike that ends at a brewery. It also looks right with corduroy pants and a down vest around town. For snow deeper than the 5 inch height, the buff Sorel Caribou takes over.

Skip it if: Skip it if you want a light boot, since the pair weighs 58 ounces.

Shop it at Danner

Best true work boot

16. Chippewa Super DNA 6 Inch Waterproof Lace-Up in Charcoal

Comfort

4/5

Walkability

4/5

Dresses up

1/5

Weather ready

5/5

Chippewa built the Super DNA as a real work boot, with waterproof full grain leather and a moisture wicking Dri-Lex lining. A removable Ortholite insert, a triple ribbed steel shank, and a Goodyear welt add support and durability. The Vibram Tacoma TC4 Plus outsole resists oil and slipping, and the boot is rated for electrical hazards.

Wear it on the job with canvas work pants, a thermal henley, and a duck jacket. Off the clock it pairs fine with dark jeans and a flannel. If you want work boot style without the safety features, the Oro Legacy Red Wing Classic Moc is the classic choice.

Skip it if: Skip it if you want a boot for style alone, since this one is made for job sites first.

Shop it at Chippewa

Best harness boot

17. Frye Harness 8R Boot in Black

Comfort

3/5

Walkability

2/5

Dresses up

2/5

Weather ready

3/5

Frye's Harness 8R is the classic motorcycle style boot, with a square toe, an 8 inch shaft, and a harness strap across the ankle. It is made of greasy leather on a Goodyear welt and left unlined, and Frye says it gets even better with age. A neoprene outsole that resists oil keeps it practical on a garage floor.

Frye suggests simple black fitted jeans, and that is the right call. Add a white tee and a black leather jacket for the full look. In fall, a gray hoodie under a waxed jacket keeps it feeling current.

Skip it if: Skip it if you want a boot that hides under trousers, since the 8 inch shaft and harness are meant to show.

Shop it at Frye

Best winter Chelsea boot

18. Blundstone Thermal 566 Chelsea Boot in Black

Comfort

5/5

Walkability

4/5

Dresses up

2/5

Weather ready

5/5

Blundstone's Thermal 566 is the winter version of the brand's Chelsea, with black waterproof leather and Thinsulate insulation. Inside, a contoured EVA footbed with XRD Technology is lined in sheepswool, and the genuine shearling footbeds are removable. The brand says it is ready for snow, rain, slush, and sleet, and the latexed seams and TPU outsole back that up.

Wear the 566 with dark jeans, a fisherman sweater, and a wool peacoat on icy commutes. It also works with black cords and a puffer jacket on the weekend. In spring, hand the job back to the stout brown Blundstone Original 500.

Skip it if: Skip it if your feet run warm, since the insulation is made for real cold.

Shop it at Blundstone

Best cozy casual boot

19. UGG Neumel in Light Bronze

Comfort

5/5

Walkability

4/5

Dresses up

1/5

Weather ready

2/5

UGG lines the Neumel fully in UGGpure wool, cushioned footbed included, so it feels like a slipper with laces. The upper is full grain leather or suede with traditional lacing, and the Treadlite by UGG outsole adds traction, cushioning, and flexibility. At 12.58 ounces, it is a light, easy boot for days off.

Wear the Neumel with joggers, a crewneck sweatshirt, and a fleece jacket for coffee runs. It also looks relaxed with straight jeans and a chunky cardigan. When the forecast turns wet, switch to the black Blundstone Thermal 566.

Skip it if: Skip it if you need a boot that can handle slush or a dress code.

Shop it at Zappos

Best snow boot

20. Sorel Caribou in Buff

Comfort

3/5

Walkability

2/5

Dresses up

1/5

Weather ready

5/5

Sorel's Caribou pairs seam sealed waterproof leather with a handcrafted vulcanized rubber shell. A removable 9mm ThermoPlus felt InnerBoot and an acrylic and wool blend snow cuff keep the warmth in. The AeroTrac rubber outsole is designed not to clog with snow, and the 10.5 inch shaft sits well above the ankle.

Wear the Caribou with insulated pants, a down parka, and a knit beanie on the worst days of winter. It also works with jeans, a flannel, and a quilted jacket for shoveling the driveway. Once the snow melts, the brown Danner Mountain Light is ready for muddy trails.

Skip it if: Skip it if you mostly walk city sidewalks, since it weighs 2 pounds 11 ounces.

Shop it at Zappos

What are the best boots for men who only want one pair?

Go for a brown leather lace-up or Chelsea with a rubber sole, since it works with jeans, chinos, and most casual office clothes. The Thursday Captain and the Blundstone Original 500 are our top two for exactly that reason. Add a waterproof or insulated pair later if your winters are harsh.

Which men's boots on this list are waterproof?

Look for a brand that says waterproof, not just water resistant. The Danner Mountain Light, Chippewa Super DNA, Sorel Caribou, Blundstone Thermal 566, and both Cole Haan boots all state waterproof construction. The Blundstone Original 500 is water resistant, which handles drizzle but not standing water.

What should men wear with boots?

Straight or slim jeans that break once at the top of the boot are the easiest match. With chinos or wool trousers, choose a sleeker boot like a Chelsea, a dress boot, or a plain toe lace-up so the hem sits cleanly. Save chunky lug soles and snow boots for jeans, cargo pants, and heavier outerwear.