Skip to main content

10 of 2021’s Best Pants To Wear This Fall and Winter

It’s time to start thinking about pants again. While we spent most of our winter inside, this year is allowing us more of an opportunity to be out and about, and with that means a chance to invest in some new threads to rock for when you want to make a splash. Although, you may notice now that the best men’s pants look a little different than they did previously.

Yes, the trend in pants right now is to go slightly larger. Of course, you don’t need to totally get rid of your tailored or even skinny jeans, but working in some larger cuts is definitely a way to add some good variety into the mix. You’ll also notice pleats are back, giving a bit more character and formality to your trousers.

As you begin to shop for new fall and winter wares, be sure to consider some new pants, too. To help you make your decision even easier, we’re rounded up 10 of our new favorites for 2021. Our picks, below.


1. Todd Snyder Italian Cotton Gurkha Pants

More often than not, some of the best clothing comes about when new techniques are merged with old classics. This is the case with Todd Snyder’s Italian Cotton Gurkha pants, a refreshed update of classic British military-style pants. The double-pleated front and self-belted waist add fun and inspired vintage details to what is otherwise an extremely modern fit. Oh, and the color is just perfect, with the rich olive tones making them perfect for wearing with boots in the fall.

Lazy loaded image
Todd Snyder


2. Rowing Blazers Zig-Zag Cotton Pants

Despite what you may have heard to the contrary, you can wear white after Labor Day. And if you’re going to do so, you should wear these pants from Rowing Blazers. Slightly oversized, the legs are a little wider than you may typically be used to, but don’t let that deter you from trying them. The brand’s already sporty feel is further refined by adding their signature zig-zag pattern to the sides, almost as if to evoke feelings of Adidas track pants, but far dressier.

Related Stories

Lazy loaded image
Rowing Blazers


3. Polo Ralph Lauren Stretch-Cotton Twill Pants

If you want your pants to have the comfort of sweats but the structure of something you can wear to the office, these stretch-cotton twill pants from Polo Ralph Lauren will be your favorites. The cotton-twill makes these chino-style pants super, super comfortable while providing a look that’s great for daily wear. Plus, there’s even an adjustable waistband to make an already comfy fit even better.

Lazy loaded image
Mr. Porter


4. lululemon Classic ABC Pant

With just about every single color imaginable offered, the classic ABC (which stands for anti-ball crushing — yes, we’re serious) pant is meant to provide you elite comfort no matter if you’re at home or on the go. Crafted from Warpstreme fabric, the pant is quick-drying, stretchy, breathable, and even wrinkle resistant. Classic-looking in every way possible, you’ll likely never want to take them off once you’re worn them.

Lazy loaded image


5. Taylor Stitch Chore Pant

Having a suitable pair of workwear pants in your wardrobe is an absolute must for this year, and it’s well worth considering this pair from Taylor Stitch. The heavier-quality materials in the pant make it so they can take a beating, while fun details like the reinforced knees make the pants extremely sturdy. Plus, the Boss Duck fabric makes for a really sharp-looking appearance that will go with just about anything you pair it with this fall.

Lazy loaded image
Taylor Stitch


6. Gap Vintage Khakis

Considering Gap made a name for themselves with their khakis, you can never go wrong investing in a pair of their vintage-style pants. Offered in a handful of color hues, these khakis have been infused with GapFlex tech that will make them comfortable and cozy during extended wear and can go from your home to the bar and back without breaking a sartorial sweat.

Lazy loaded image


7. Billy Reid Cotton Cashmere Terry Drawstring Track Pant

Sometimes you just want to slip on a pair of pants that are so comfortable you’ll practically live in them. That’s the case with these track pants from Billy Reid. Made from a blend of cotton and cashmere, they’re incredibly soft. The ribbed cuff at the bottom makes them great to wear when you want to show off some cool new kicks. It’s easy to imagine tossing these on for your weekend errands time and time again throughout the fall.

Lazy loaded image


8. Outerknown Voyager Utility Pants

Modeled after old fatigue-style pants, Outerknown’s Voyager Utility Pants are cut slightly larger than your standard pair of men’s pants. They are meant to provide some form to them while also being super comfortable. Which means they’re great to wear pretty much whenever you want. Additionally, the tabs in the back of the pant make it so you can easily adjust their fit if you want to have them sit a little bit more snug on the waist. Plus, they’ve been garment dyed to ensure the best look.

Lazy loaded image


9. Goldwin Lounge Easy Pants

A nearly perfect three-season pant, Goldwin’s Lounge Easy pants are mean to take you from spring to fall without worry. The stretchy, quick-drying fabric is cut with a slight taper to them, providing a silhouette that’s tailored but not skinny, straight, but not too baggy. In short, they’re perfect pants to wear pretty much whenever you need to put on a pair.

Lazy loaded image


10. SMR Days Bondi Pleated Cotton-Corduroy Pants

The blend of cotton and corduroy of these pleated men’s pants from SMR Days creates a unique combination; the cotton helps to make the heavy nature of the corduroy not as hot, while the corduroy helps to give the cotton some structure. In short, they’re striking looking and feeling pants, bolstered by the front pleats and elastic waistband to make a perfect symmetry between formal and casual.

Lazy loaded image
Mr. Porter


Best Leather Jackets you Can Buy Online