Step Up His Boot Game with These Comfy and Stylish Picks

Graphic by Giovanna Pineda/KCM

These boots were made for walking.

Boots are a staple wardrobe piece in colder months, but they’re also a great year-round essential. Not only do they protect your feet and toes from frigid temps, but they can add a dose of style to an otherwise bland outfit. Why not pass along this not-so-secret secret to the man in your life?

Men’s boots come in a ton of different styles, but sometimes you have to search through pages upon pages of hiking and work boots online before you find something a little more elevated. Whether your man is looking for a leather pair he can wear out on date night or to the office, a pair that’s made for exploring the great outdoors, or he wants a pair that’s a replacement for his everyday sneakers, there’s something out there to fit his style and desired comfort level.

Here, we’ve rounded up some boots for men that combine comfort and form in a range of prices and styles. Add a little pep to your man’s step with these classy boots that he’ll be wearing just about everywhere.

Best Boots for Men

Nisolo All-Weather Mateo Boot

Nisolo

These waterproof boots are definitely more chic than a rubber rain boot. Made with sustainable materials by artisans who are paid a living wage, this is a shoe that will last a lifetime. It comes in both rough and smooth leather styles and four different colors, all coming with a memory foam insole and shock-absorbing rubber outsole.

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Everlane Desert Boot

Everlane

If he’s a minimalist, these sleek desert boots will fit right into his wardrobe. The light gray color goes with about anything, but the boots also come in black and brown suede if he prefers a more traditional neutral. With a fit like a sneaker but a polished boot look, he’ll be wearing these all season long.

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Nunn Bush Denali Plain Toe Chukka

Zappos

He can go from work to dinner in these classic chukka boots. They’re made of smooth leather that looks just as great with a pair of slacks as it does jeans. The rubber sole has tons of traction (unlike more classic leather outsoles), and the leather upper is waterproof, perfect for rainy or snowy days.

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Rodd & Gunn Kingsview Road Chelsea Boot

Nordstrom

A Chelsea boot is probably something you have in your own wardrobe, and it is something he’ll gravitate toward in his, too. An elastic panel on the side makes these easy to slip on and off, while the dark coloring on the toes and heels gives it that perfect worn-in look straight out of the box.

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G.H. Bass & Co. Mens Benton Tumbled WX Casual Sneaker Boot

Walmart

He’ll be willing to replace his go-to sneakers with this sneaker-boot hybrid thanks to how comfortable they are. While this looks like a boot, the insole is extra cushy, and the faux leather outer is breathable and flexible, meaning he won’t need to break these in before wearing them out.

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Chaco Revel Chelsea Boot

Nordstrom

Chaco is known for their comfy strappy sandals, but they also make cozy boots. These are more of a slipper than an outdoor boot, but they could definitely be worn outside the house in dry climates. An elastic panel on the side means they’re easy to slip on and off, and they come in four colors to suit his fancy. Despite the soft look and feel, the insole has built-in arch support to keep his feet from getting sore.

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Timberland Men’s Graydon Sneaker Boot

Amazon

Timberland is known for their classic work boot, but they also make stylish boots for everyday wear. They’re just as supportive as the brand’s classic boot, with laces going up above the ankle, and perhaps more comfortable thanks to the sneaker-like memory foam sole. They’re also waterproof.

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On Cloudrock Waterproof Boot

On

These take hiking boots to the next level. Fans of On’s running shoes will love their hiking boots, which are just as comfortable and lightweight as their sneakers. A rugged sole lends itself to traction of rough terrain, and a waterproof upper means he can tromp through puddles and shallow streams without getting wet feet.

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Blundstone Dress Chelsea Boot

Zappos

If he wants to add a little color to his wardrobe, these oxblood boots are a great start. The maroon color is pretty neutral, but still stands out, and the color will develop a nice patina with wear. Pull tabs on either side of the boot make them easy to slip on and off, while a rugged sole makes them great for walking in the city or taking a stroll on some trails.

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L.L. Bean Shearling Lined Bean Boots

L.L. Bean

His toes will stay toasty in these shearling lined duck boots. A rubber upper keeps his feet dry, and the soft leather boot shaft makes it easy to move around and break in. The sole of these classic Bean boots are great for snow and rain, and the high lacing allows him to adjust the tightness to his liking.

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J. Crew Nordic Waterproof Hiker Boots

J. Crew

Despite being neutral, these color-blocked hiking boots make a playful statement. The navy looks amazing against the tan leather, and bright red pull tabs and stripes have reflective stripes for visibility in the dark. Even though these are pretty boots, they’re also made to handle rugged terrain and weather, so he’ll always be ready to lace up and head out — even if it’s just to a brewery.

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