With their durable construction and laid-back style, pull-on boots can work hard during the day and transition seamlessly into evening hangouts.
When your to-do list won’t let up and foul weather is on the horizon, you need to step into boots you can count on. Or rather, that’s when you need to pull on a pair of boots you can count on. That’s right: Ditch the laces and opt for a pair of rugged men's pull-on boots. We’re not talking about a pair of sleek Chelsea boots here. With their elastic side gores and durable, hard-wearing designs, the men’s boots in this guide lean more towards workwear than cocktail hour.
Pull-on boots could quickly become the most useful pair of spring shoes you own. Similar to a field jacket or waxed trucker jacket, these shoes combine utilitarian functionality (like what you’d get with a pair of men’s work boots) with casually rugged style, which makes them perfect for everyday wear.
How to Style Pull-on Boots
The pull-on boot rests in the middle of a footwear Venn between hardcore work boots and dressy pairs you can wear with a suit. They're neither a lace-up steel-toe boot nor a traditional Chelsea boot; you can wear them for outdoor work or events that call for a casual dress code.
Features to Look for in Pull-on Boots
Thanks to the elastic side gores on the uppers, pull-on boots are easy to put on and take off, even when you’re dressed in bulky workwear (like canvas pants or a canvas shirt jacket), and they deliver the same functionality as lace-up boots. They’re designed to take a beating, and they’re often made with thick leather uppers, a roomier toe shape, and grippy outsoles (sometimes made by a company like Vibram).
There are also pairs of pull-on boots that boast a rubberized design, not unlike a rain boot—they’re ideal for keeping your feet warm and dry in wet conditions all year round.
Whether you wear yours for a day of yard work or a visit to your favorite brewery, the pull-on boot delivers durability and hardworking style in spades. Read on to find your new go-to pair of men’s boots.
The Best Men's Pull-on Boots of 2023
1. Blundstone #500
Blundstone boots are about as legendary as it gets, and they have a heritage that can be traced back to Australia in the 1800s. The #500 Boots date back to the 1960s, and they define what pull-on boots should be: easy-access elastic gore sides, front and back pull tabs, a leather upper that gets better with age, and a lightweight-yet-sturdy rubber outsole.
[$210; blundstone.com]
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2. Filson Roper Boots
For more coverage above your ankle, opt for the taller shaft height of Filson’s tough-as-nails Roper Boots. The three-quarter composite shank delivers exceptional durability, and a Vibram outsole ensures traction on treacherous surfaces. They’re also made with a Goodyear welted sole, so you can get them resoled when the bottoms wear out.
[$398; filson.com]
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3. Red Wing Heritage Weekender Chelsea
Searching for something a bit more suited for play than work? Red Wing’s Weekender Chelsea will be comfortable and stylish right out of the box. It features rich copper leather on the upper, and it’s designed to be flexible, so there’s no break-in period. On the bottom, these boots feature the company’s ComfortForce footbed for a comfy step-in feel and a durable wedge-shaped Hill outsole.
[$260; redwingshoes.com]
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4. XTRATUF 6-inch Ankle Deck Boot
Fishermen in frigid seas trust XTRATUF footwear to keep them upright on slick deck surfaces in choppy conditions. These definitely fall on the workwear end of the men’s boots spectrum, but if you need a hardworking, waterproof, slip-resistant boot, they’re a great pair to go with.
[$115; xtratuf.com]
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5. All-Weather Pull-On Storm Boot
If you prefer the streamlined feel of an ankle boot instead of pull-on boots with a tall shaft, All-Weather has dreamed up the perfect pair. The brown nubuck leather upper is stylish, can stand up to nicks and scrapes, and is 100-percent waterproof. It also features a shock-absorbing midsole for a comfy ride, and the Vibram Megagrip outsole provides good traction on city streets or rocky trails.
[$158; huckberry.com]
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6. Swims Charlie Rain Boot
The pull-on rain boot gets a modern upgrade courtesy of Swims. The Charlie is made from vulcanized rubber for reliable protection from wet weather, and it features an anti-slip grip outsole and a chunky, eye-catching design.
[$120; us.swims.com]
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7. Huckberry x Blundstone #1320 Chelsea Boot
What do you get when a retailer known for tough, go-anywhere gear teams up with the legendary boot brand Blundstone? You get a distinctive pair of pull-on boots. The 1320 features a TPU outsole, two sets of footbed inserts for a snug, comfortable fit, and a rich brown water-resistant leather upper. The sense of adventure built into this pair isn’t half-bad, either.
[$225; huckberry.com]
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8. Tecovas Knox
The roper boot design hails from the Wild West, but it’s a standout style no matter where you live. The tall shaft height delivers crucial coverage for outdoor activities, and the wedge outsole cushions your foot and generates reliable traction. This boot is also available in wide sizes—a boon for guys with bigger feet.
[$245; tecovas.com]
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9. Danner Bull Run Chelsea
Heritage leather meets an oil- and slip-resistant outsole in this pair of dependable work boots. While they’re built to handle long days on the job, you can also pair them with dark blue jeans and a stylish chambray shirt for a cool off-duty look.
[$230; danner.com]
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