These Are The 10 Hottest Men’s Fashion Trends for Fall and Winter 2021

mens fall fashion guide
Courtesy of Checks Downtown, Tecovas, Mr. Porter
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As the lazy, hazy days of summer begin to fade, it’s time to start thinking about fall and winter. More specifically, it’s time to start thinking about fall and winter fashion. After a season spent indoors during the pandemic, now is the time to really start dressing, allowing the colder temperatures to help you to break out your best sweaters, jackets, pants, and more. But it can be overwhelming to figure out just what to wear, especially having been inside for so long. But don’t worry, we’re here to help.

To help you figure out what to wear this fall and winter, we’ve rounded up ten of the hottest men’s fashion trends for you to know about heading into the last half of the year. Some of the trends on this list may surprise you, but they will for sure make you the coolest looking dude on the block. Check out our picks below.


1. Seeing Red

After a year stuck inside, it’s time to make a bold splash. Red, specifically a brighter, almost fire engine-type hue, is a fantastic way to make some noise this fall. While red shirts are great (even better if you’re wearing a wool or flannel shirt), the real move here is to go for some red outerwear. Red jackets like this one from L.L. Bean evoke feelings of James Dean in Rebel Without a Cause, although you can certainly go bolder and rock an all-red coat, too, if that’s your bag. Regardless, working in a red piece or two is a quick and easy way to elevate your fall wardrobe.

L.L. Bean Waterproof Windbreaker Jacket

L.L. Bean Waterproof Windbreaker Jacket L.L. Bean

L.L. Bean Waterproof Windbreaker Jacket



2. Pleats

After years of skinny jeans dominating, it’s time to go big (or go home) regarding the size of your pants. But there’s a new wrinkle with wider pants: pleats. Famously left behind in the 90s, pleats have returned to give your pants some character, adding just a bit of attitude to a pair that might otherwise be kind of plain. You can definitely grab a pair of pleated pants in solid colors, but we advocate for going truly wild with your pleats and reaching for a pair like this from New Zealand outfit Checks Downtown to really shake things up.

Checks Downtown Leopard Print Pleated Pants Checks Downtown

Checks Downtown Leopard Print Pleated Pants



3. Wild Wild West

It turns out “Old Town Road” didn’t just make an impact on Lil Nas’ career, but also the fashion industry, too. Western-ware is back with a vengeance, like a grizzled sheriff making one last stand against the robbers of a frontier town. Sure, you can reach for western-style button-up shirts or even boot-cut jeans, but the easiest way to get on the saddle is with a pair of cowboy boots. We really like this set of roper-style boots from Tecovas. Roper boots aren’t quite as intense as cowboy boots, and this particular pair comes in a beautiful, supple suede that we love. Wear them like you would a pair of Chelsea boots, and you may end up liking them too much to ever take off.

Tecovas “The Shane” Suede Roper Boot

Tecovas The Shane Suede Roper Boot Tecovas

Tecovas The Shane Suede Roper Boot



4. Tone it Down

A quick way to show that you really know how to dress is to put together a tonal ensemble. This fall, specifically, the color to use is variations on camel-colored hues. Pairing something like this Billy Reid V Neck sweater with a pair of chinos, a white dress shirt, and some white or even brown sneakers is a great way to dress this fall. The brown caramel hues evoke a 1970s-style look that’s now bold and fresh in 2021.

Billy Reid Saddle V Neck Sweater

Billy Reid Saddle V Neck Sweater Amazon

Billy Reid Saddle V Neck Sweater



5. Tanks for the Memories

Tank tops? Yeah, you heard us right. Great for wearing as a casual shirt around the house or (as we’d recommended) as an easy way to layer under a patterned shirt, tank tops are back in fashion to let you channel your inner Tony Soprano. Layering a tank under a shirt is a great way to give your outfit some depth without getting overly hot, which is particularly handy on those days where it’s cold in the morning but warms up by midday. We like this tank from Mack Weldon because the ribbed nature gives some fun texture to it while also being pretty affordable given its quality.

Mack Weldon 18-Hour Jersey Rib Tank

Mack Weldon 18-Hour Jersey Rib Tank Mack Weldon

Mack Weldon 18-Hour Jersey Rib Tank



6. Big Coats

A coat should feel like you’re wearing a cape; it should be a little drapey, a little oversized but polished, and cool enough that you feel like you’re about to take off at any moment. This fall also sees the return of a trench coat (a further continuation of 70s style), so why not combine the two? This option from Todd Snyder is actually a three-in-one trench with a built-in liner to keep you extra warm during the winter. Plus, its color makes it more Three Days of the Condor than Inspector Gadget, which is what you want when considering a trench coat.

Todd Snyder 3-1 Italian Trench Coat

Todd Snyder 3-1 Italian Trench Coat Todd Snyder

Todd Snyder 3-1 Italian Trench Coat



7. Vested Interest

Another trend that’s back? The sweater vest. The key difference here and sweater vests of old is getting one with a crazy pattern that lets it be a real statement piece. There’s no wrong way to rock one either, whether it be over a tee, with a collared shirt, or even on its own. This one from Ralph Lauren gets double points for its striking fair isle print and for having buttons on it, which adds to its sophistication level.

Ralph Lauren Fair Isle Sweater Vest

Ralph Lauren Fair Isle Sweater Vest Ralph Lauren

Ralph Lauren Fair Isle Sweater Vest



8. Leather Weather

Leather jackets are one of those things that never quite go out of style. Yet, this fall is seeing a move away from more traditional leather jackets to more leather-style coats. For example, The Weeknd just showed up in his latest video, rocking a full leather trench coat. While you probably don’t need to go that far, opting for something like this faux leather double-breasted coat from Topman is a great way to get in on the trend. In short, your leather rotation this fall should be closer to something you’d see in The Matrix than something you’d see in Grease.

Topman Double Breasted Faux Leather and Faux Shearling Coat

Topman Double Breasted Faux Leather and Faux Shearling Coat Nordstrom

Topman Double Breasted Faux Leather and Faux Shearling Coat



9. Statement Knits

In the same way you’d want to go big and bold with your sweater vest, you should look to do the same with a cardigan. Perfect for layering (either over a shirt or over a hoodie like I did here), cardigans are a great way to keep cozy and warm with little effort. Bonus points if you can find a patchwork cardigan like this one from Beams Plus, which provides an atypical pattern to pair with all of your clothes, letting it be the standout portion of your wardrobe and ensemble.

Beam Plus Patchwork Cardigan

Beam Plus Patchwork Cardigan Mr. Porter

Beam Plus Patchwork Cardigan



10. Suited Up

Listen, we get that getting dressed up takes a lot of effort. But, the results can’t be denied. As things open back up, we believe there’s a natural desire to looking polished after a long time living in casual clothes. This means that, yes, it’s time to get yourself back in a suit. Don’t feel like you need to put back on your dress shirts, though; it’s perfectly fine to rock a suit with a tee underneath. However you wear it is up to you, but make sure you’ve got one in your rotation.

Ludlow Slim-fit Suit Jacket

Ludlow Slim-fit Suit Jacket J. Crew

Ludlow Slim-fit Suit Jacket


Ludlow Slim-fit Suit Pant

Ludlow Slim-fit Suit Pant J. Crew

Ludlow Slim-fit Suit Pant



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