The Best & Most Stylish Types Of Winter Pants for Men


Your wardrobe of Effortless Gent-approved essentials needs the right tools for the job, like warm winter pants. When temps drop and snow blankets the ground, you’re not exactly reaching for sneakers…. you’re grabbing your trusty snow boots! Same idea goes for your pants in colder weather. 

We’re not quite going full-on technical with snow pants. There’s a way to shop the best men’s winter pants while scoring seasonal style points and adding comfort to your wardrobe.

We’ve come up with a fun, eclectic mix of styles, formality levels, fabrics, and colors for the fall and winter season. You’re bound to find something that works for your cold weather wardrobe.

So step it up in a major way with the right pair of men’s winter pants. Check out our prime selections below.


Flannel Trousers

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Spier & Mackay Donegal tweed trousers, SuitSupply Sortino Trousers

Once thought of as perhaps stuffy or even boring, flannel trousers as an excellent option in terms of warm winter pants for men.

We love the versatility of grey flannel trousers, with a look that can go a touch more rugged (with a quilted jacket and lace-up dress boots) or refined (with a blazer and tweed vest).

Flannel is commonly paired with a matching suit jacket, but they can certainly function plenty well on their own. Pinpoint the right pair with Spier & Mackay, which sells an excellent pair of medium gray flannel trousers with a higher rise for a classic look. 

You’ll largely find flannel trousers in shades of gray for a truly timeless look, like Spier & Mackay’s medium gray tweed pair. They’re like your go-to spring and summer dress pants, only done up in a proper pair of pants for cold weather.

If you’re feeling especially dashing, SuitSupply makes the handsome, belted Sortino Mid-Grey Trousers from rich Italian flannel, then finishes it with an eye-catching, built-in belted front.

Dark Blue Denim

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Levi’s 501 Denim Jeans

Some picks never go out of style, regardless of season, and a pair of the best dark wash blue jeans qualifies as a pair of warm pants for men you can rock at any time.

In the same way that you rely on a pair of lightweight, light wash jeans in the spring and summer, your tried-and-true, heavier weight, dark blue jeans are the proper way to go in the winter.

The sturdy, dark blue cotton denim has more heft and weight than light wash cotton denim, which makes it ideal for brisk days.

And in the right cut, from the right brand, it’s only going to get better with age as they develop their own character – and the Levi’s 514 is just the ticket. The slim-straight fit is classic and flattering, while the dark color is rich and can be worn in rugged or business casual fashion.

If you have a more athletic build, or you want a bit looser of a fit, try Levi’s 541 Athletic Tapered Fit or the Levi’s 501s for a classic straight leg look.

Moleskin Pants

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Bonobos Moleskin Trousers

Certain fabrics were practically dreamed up for winter, like the sturdy, woven cotton of moleskin, with a brushed surface that calls to mind suede.

Moleskin trousers also have a nice, substantial drape – like a thicker version of a chino, with just as much utility and versatility.

They tend to look right at home with luxe winter style staples, like a turtleneck or a shawl cardigan, and like the chino, they can be dressed up or dressed down a touch.

The moleskin fabric makes them pricier than a standard pair of chinos, but Bonobos’ Stretch Italian Moleskin Trousers check the proper boxes when it comes to distinctive cold-weather colors and premium Italian stretch fabric.

Seasonally Colored Pants

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Colorful Trousers from Brooks Brothers, Bonobos, Peter Christian

One of the best parts about dressing for a new season lies in fully embracing the shades of that season, and rich, warm colors are right at home in the chillier months.

In the same way that vivid shades of light blue or olive are prized in the spring and summer months, deep shades of burgundy, tobacco and indigo (among others) are part of the color wheel of warm pants for winter.

It’s a great opportunity to try out vivid colors you might not normally wear, perhaps in a shade like the deep plum of these crisply designed Peter Christian Imperial Moleskin Pants.

And finding the right blend of seasonal fabric (like corduroy) and eye-catching color options has never been easier – the Bonobos Five-Pocket Corduroy Trousers check both boxes handsomely.

Winter is also an optimal time to experiment with different variations on classic fabric and fit – these traditional-fit Brooks Brothers corduroy trousers feature distinctive pleats, a clean tab-front waist closure and a classic fit in handsome colors.

Flannel-Lined Chinos

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Flannel-lined pants from Flint & Tinder, L.L.Bean

The trusty chino gets a rugged, comfortable and ultra-warm upgrade for winter. Flint and Tinder, best known for its hard-working waxed trucker jackets, sets its sights on the chino and ramps things up a notch with the Flannel-Lined Guide Pants.

They modeled this pair after U.S. Army trousers, and crafted them from a substantial yet supple Bedford cord fabric. The real kicker is the double-brushed cotton plaid flannel, which calls for a nice ankle cuff for a shot of stylish contrast.

L.L.Bean Double L Chinos

“Fully lined with soft, warm flannel, these classic cotton men’s lined plain front khakis are just right for the cold days of winter through the first chilly days of spring.”

Shop L.L.Bean

L.L. Bean’s famed Double L Chinos are another pleasingly rugged winter option to pair with your winter Bean Boots.

They feature a roomier straight leg and come in two color (and liner) options, each as well-suited for a winter day as the next. The cotton chino fabric should prove durable and the liner should serve you well on brisk days.

Corduroy Pants

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Selection of Cords from J. Crew

Among all the fabric varieties on the market in your search for the best men’s winter pants, corduroy is the one that might come up the most often.

Named for the textured vertical ridges running the length of the fabric (known as the “wale”), corduroy drapes nicely and provides more warmth than denim or the timeless chino.

Corduroy can be worn in versatile fashion, but has a slightly dressier finish than blue jeans. For instance, J. Crew makes a classic straight-fit pair of corduroys in deep shades of tan, purple and more.

This time, they also feature comfort stretch for easy movement all day long.

Herringbone Trousers

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Spier & Mackay Herringbone Trousers

One of the coolest parts – in our opinion – about shopping for a fresh pair of pants for cold weather is the array of options you have. Fabrics take on more heft and sturdiness, with warmth a key concern.

Such is the case with herringbone, especially in an elegant Spier & Mackay pair finished with refined side tabs for a clean look.

The rich brown herringbone also looks like something you’d find in a covetable pair of vintage pants. And in dressy looks and unique fabric, these are a nice change of pace from a pair of pants you’re normally used to wearing, like a dark tan chino.

Winter Sweatpants

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Todd Snyder x Champion Sweatpants

Famed American designer Todd Snyder first captured the hearts (and wardrobes) of the American man without them even necessarily knowing it, as he introduced guys to better-fitting chambray shirts and suiting through roles at Ralph Lauren and J. Crew.

His namesake line has been on much the same mission for over a decade. And Snyder is all about upgrading even the most laidback staples, like the trusty, lounge-friendly sweatpant.

The Todd Snyder x Champion sweatpants are a prime example of upgrading something ultra-casual, using soft 100 percent French Terry cotton fabric for a soft, luxe handfeel.

They’re pricier than your average pair of sweatpants, but it’s a difference you can feel right away. Weekends just got a whole lot more comfortable.

What’s Your Favorite Pair Of Men’s Winter Pants?

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Hopefully, finding pants for cold weather hasn’t left you dizzy – there’s a dizzying array of options on the market. We’re confident that your wardrobe can handle it, though. We’ll keep it simple for now.

Looking Sharp

Casual Outing

At Home

The pants in your winter wardrobe should be, well, warm and ever-so-slightly rugged. You want at home with a navy herringbone and an Oxford shirt as with a henley and Red Wing boots.

If you’re having a hard time deciding, take a step back and consider what you do on a daily or weekly basis.

  • Are you more dressed up (like for the office, client meetings, or work events)?
  • Are you working from home, or just keeping it casual in general?
  • Maybe a mix of the two?

For those days at the (formal) office or an important client meeting, you can’t go wrong with the beautiful flannel trouser from SuitSupply.

Something a bit more smart casual? We surely appreciate the Flannel-Lined Guide Pants from Flint and Tinder at Huckberry.

Oh, and for casual days aplenty that feel more stylish than sloppy, the Todd Snyder x Champion sweatpants are as polished and on-trend a pair of sweatpants can get.

Any (or all!) of these would be a fine addition to this winter’s ensemble. Shop now and thank us later.