The Best Men’s Boots for Looking Good (and Staying Dry) in Cold Weather

by Team EG  |  in Accessories

Cold weather season is upon us (and if it isn’t… it will be here soon enough). And you want to be prepared, especially with your footwear… am I right?

It’s a smart move. Today we’re gonna cover the best men’s boots we’ve come across. Read on for our picks and why exactly we love them.

A stylish pair of boots are extremely versatile, no matter the occasion or weather. Any guy who’s aiming for a smart, sharp style will benefit from one (or a few) pairs of really great boots.

man on park bench wearing jeans and brown boots sitting with legs crossed

But which types of boots are best?

  • Lace-up combat style boots?
  • Heavy duty work boots?
  • Chelsea boots?
  • Chukka boots?
  • Dress boots?

Well, the best answer depends on your overall style. Take a minute to think about what you wear most during the week.

  • In the fall and winter, are you a jeans and sweater with a peacoat kinda guy (e.g. casual to smart casual style)?
  • Are you wearing suits and sport coats most of the week (e.g. business / formal)?

I’m gonna assume your style leans a bit more casual to smart casual (which is what most EG readers gravitate towards).

Regardless, we’re gonna have a nice selection cookin’ for you today, so keep on reading.

The Best Men’s Boots for Fall and Winter: Our Favorite Pairs Overall

So while this article will outline our favorite fall and winter boots, these aren’t your only options. Use this list as a starting point, and I’m sure you’ll find something that fits your personal style.

(If you’re looking for something specific, feel free to DM me!)

Original Chippewa Service Boots

When the going gets tough, the tough get going—that adage could apply to the rugged Original Chippewa Service Boots.

chippewa brown boots

These richly crafted boots are an all-American classic. Better yet, they’ll break in wonderfully over time and pair up well with your favorite broken-in denim and classic shawl collar cardigan.

Huckberry All Weather Duck Boots

The Huckberry All-Weather Duck Boots marry the functionality of a classic pair of duck boots with the rugged style the brand is known for.

huckberry duck boots brown and black
Huckberry All-Weather Duck Boot

"The All-Weather Duckboot has the classic look of a duckboot, the all-terrain versatility and durability of a Range Rover, and comfort that rivals your favorite sneakers, all wrapped up in a waterproof rain boot you can rely on everywhere."

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They’ve blended full-grain leather and suede with outdoor-ready touches like 100% waterproof construction, a grippy Vibram outsole, and waxed laces. Wear them with tough chore pants and a thermal henley on a chilly winter morning.

Thursday Captain Boot

We’ll talk about two styles that are made for all weather conditions you’ll face this fall and winter. But the Thursday Captain Lace-up Boots are a pair that are more refined and suited for the office (or a holiday party), without sacrificing any comfort or style.

Thursday Boots Captain Leather Boots

"A well-made, rugged lace-up boot in a classic silhouette. Available in a variety of colorways and either a slim rubber or chunkier lug outsole."

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12/13/2023 03:29 am GMT

The profile is slim, the construction is high-quality, and the styling potential is nearly limitless.

Astorflex Bitflex Boots

The Bitflex boots from Astorflex are a pair of sleek Chelsea boots that maintain an air of ruggedness.

cognac colored chelsea boots astorflex
Astorflex Bitflex Chelsea Boots

Handmade in Northern Italy by a family that's been making boots for six generations, these slip-on boots are eco-friendly, handsome as hell, and represent the best value on the market.

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Made sustainably using premium materials and Italian-made construction, they’re an absurdly great value that’ll pair nicely with burgundy corduroys and a classic chambray shirt for evenings around the fire.

Danner Mountain Pass Boots

If you fancy going off-trail this fall and winter, there’s no better option that Danner. The Mountain Pass Boots are a lightweight, modern take on the classic hiking boot.

danner mountain boots dark brown

Portland-based Danner definitely knows a thing or two about the great outdoors, and it doesn’t hurt that these boots are stylish as heck.

Astorflex Greenflex Nubuck Chukka Boots

It’s smart to have a pair of timeless chukka boots in your footwear rotation for fall, winter, and beyond.

astorflex chukka boot

The nubuck leather on these low-profile chukka boots adds a nice weather-ready touch, while the aforementioned Italian-made construction makes them a surefire winner.

And of course, there’s the classic chukka from Clarks we all know and love, which is always an option.

Yuketen Maine Guide DB Boots

With Yuketen, you’re getting some of the best men’s boots on the market. Yuketen boots are exceedingly hard to come by, but worth the investment.

yuketen boots taupe color

These handsome boots channel old-school style; your father or grandfather might have worn them out in the field. If you only choose to wear them after a long day on the slopes, or during a night out at your favorite whiskey bar, well… there’s nothing wrong with that.

Thursday Boots Duke Chelsea

While I already mentioned the Bitflex chelseas from Astorflex, the Thursday Boots Duke Chelseas are my oldest and most used pair in my closet. Naturally, I have to include them in this list.

Thursday Boots Chelsea Boots

Well-made, Goodyear-welted, comfortable Chelseas in a variety of leather and suede colors.

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04/26/2023 08:38 am GMT

It’s a sharp looking Chelsea boot that can be dressed down with denim, or dressed up with wool trousers.

I tend to wear mine more casually, and they’re also a bit more beat up at this point. I’ve worn them for at least five years now. But if you keep them polished, you can definitely dress these up!

Don’t miss our article on men’s slip-on Chelsea boots, where we recommend a bunch of our other favorite styles.

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Which pair of men’s boots do you prefer? I’d love to know! Hit me up on Twitter. You can also find join other readers on Effortless Gent’s Facebook page, or DM me on Instagram.