20 Stylish, Versatile and Cozy Garments You’ll Swear by This Fall

You'll look so good no one will realize how comfortable you are

September 7, 2021 1:12 pm
An assortment of comfortable pants and tops for fall
The comfiest, best-looking pieces for fall.
Todd Snyder, Flint & Tinder

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Suffice to say, we are experiencing a bit of fatigue when it comes to the whole “return to normal” thing everyone keeps going on about. The Delta variant rages on, vaccination rates are not where they need to be, and we can’t seem to get out from under this sad blanket of uncertainty that’s been covering us for so long. 

But there are two things we know for sure. First, there’s a very good chance you have spent more time than usual over these past 18 months wearing clothes that would not traditionally be considered office-appropriate. Second, despite what we just established, there’s a very good chance you are being asked to return to the office in some capacity in the near future. 

This creates something of a conundrum. If you’ve been splayed out on your couch in basketball shorts and a ratty T-shirt all summer, following a winter and spring you spent in sweatpants and a hoodie, you’re probably not exactly eager to put on your starchiest button-down and your stiffest jeans. 

Fortunately, the menswear landscape is currently lousy with options for people looking for clothes that are comfortable, unfussy and non-restrictive but still stylish and perfectly put together. Below, we’ve chosen 10 tops and 10 bottoms that’ll help you look and feel good this fall, whether you’re on your couch, in the office or anywhere in between.



lululemon Fundamental Long Sleeve Henley

The henley is quite possibly the most efficient half-step from casual to professional. It’s fancier than just a long-sleeve T-shirt, thanks to the buttons, but because of its collarless neckline, it’s not quite as big a leap as a button-down or even a polo. A good henley like this one from lululemon will work brilliantly in a number of different settings, adding a nice, subtle dose of rugged masculinity to your look with minimal effort.


lululemon At Ease Hoodie

For those days when you’re working all by your lonesome at home, save for the occasional Zoom meeting. lululemon’s At Ease hoodie is a remarkably comfortable garment made with a 4-way stretch fabric that gives it a bit of texture and helps it stand out from all your other hoodies.


Vuori Ace Button-Down

If you find yourself having to put on an actual collared shirt for the first time in a while, there’s probably no better option than Vuori’s Ace Button-Down, which is constructed with the brand’s Performance Piqué fabric. It’s soft and comfortable, but with some nice features like anti-odor tech and UPF protection.


Faherty Movement Knit Shirt

If performance fabrics, like in the Vuori shirt above, aren’t your style, this Faherty button-down is made of an ultra-soft cotton blend that belies its more … buttoned-up silhouette.

Todd Snyder

Todd Snyder Turtleneck Sweatshirt 

Admittedly, in most parts of the country, it’s still a little too warm to get away with a turtleneck, but soon enough, this will be your closet’s MVP. Part of Todd Snyder’s now-legendary Champion collaboration, this is the ultimate in sly comfort. Everyone will be all, “Ooh, how stylish and elegant!” And you’ll be all, “Thank you, I really care about fashion!” but deep down you’ll just be like, “heh, it’s just a sweatshirt.”

Outdoor Voices

Outdoor Voices MegaFleece Snap Sweatshirt

This fall, even more so than all the falls that came before it, we think you’re gonna get a lot of mileage out of your collection of pullover fleeces and quarter-zips. Worried about coming off a little too basic-bro-ish? Don’t be. Just make sure you choose one with a little bit of character and don’t be afraid to lean into a slightly oversized fit.


Flint & Tinder Jackson Flannel

Another piece that does an excellent job of concealing how comfortable it is, Flint & Tinder’s Jackson flannel offers the softness and flexibility you’d expect from the fabric, but since it’s done up in a solid color rather than a more outdoorsy plaid, it’ll work just fine in a more formal setting.


Faherty Inlet Knit Blazer

We’ve been saying for years that no one does soft quite like Faherty, so if you’re looking for an outer layer that’ll add a touch of elegance to whatever your base layer is, you could do far worse than this knit piece, which is cut like a blazer but has the spirit of an overshirt or a chunky cardigan.


Patagonia Recycled Cashmere Quarter-Zip

Like we said, quarter-zips are the way to go this season. Throw it over a button-down for an immediate dose of smart business casual or over a T-shirt to rake some leaves.

Reigning Champ

Reigning Champ Midweight Terry Crewneck 

Reigning Champ’s signature crewneck sweatshirt is slim-cut and clean enough that it doesn’t read like a sweatshirt at all, but more like a cotton-cashmere sweater.


ABC Jogger 30" Warpstreme
ABC Jogger 30″ Warpstreme

lululemon ABC Jogger

So yes, we realize these are not exactly going to pass for chinos or anything, but that’s not to say they can’t still be a part of a smart, presentable getup. lululemon’s massively popular ABC joggers are soft enough that you’ll want to live in them but also streamlined enough that you’ll never look sloppy.

Club Monaco Tapered Cotton Trousers
Club Monaco Tapered Cotton Trousers
Mr P

Club Monaco Tapered Cotton Trousers

With an elasticized waistband and leg openings, these Club Monaco trousers are pretty much everything we could ask for this season, allowing for a little stretch thanks to that waistband, added mobility thanks to the relaxed seat and thigh, plus a more polished look thanks to the tapered cuffs.

Commission Pant Classic 32" Warpstreme
Commission Pant Classic 32″ Warpstreme

lululemon Commission Pant

The Commission Pant from lululemon has “go-to pair of pants” written all over them. The highly technical fabric is thin and moisture-wicking, and the classic fit allows for plenty of movement, whether you’re biking to work and could use the added mobility or you just desperately do not wish to feel constricted in any way.

Flint and Tinder 365 Jogger
Flint & Tinder 365 Jogger

Flint & Tinder 365 Jogger

Joggers with belt loops are the biggest lie ever told to man. And we are very, very happy to be lied to.

Taylor Stitch Après PantAprès Pant
Taylor Stitch Après Pant

Taylor Stitch Après Pants

The most striking thing about these Taylor Stitch Aprés pants are the double cloth waffle-knit fabric, which makes them look almost like herringbone dress trousers when they are in fact some of the most comfortable lounge pants you’ll ever wear.

Jersey Relaxed Ankle Pant
Jersey Relaxed Ankle Pant

Uniqlo Relaxed Ankle Pants

If there’s ever a time to see if you can pull off the cropped, slightly oversized look, it’s right now. Pair these with some smart, minimalist sneakers and one of those quarter-zips we mentioned above, and no one will even realize how comfortable you are.

The Performance 5-Pocket Pant
The Performance 5-Pocket Pant

Everlane Performance 5-Pocket

Made from a soft and unrestrictive fabric, and cut in a silhouette you won’t have to think very much about, Everlane’s Performance 5-pocket pants are exactly the kind of versatile no-brainer we’re all looking for this season.

770™ Straight-fit pant in corduroy
77 Straight-fit pant in corduroy

J.Crew Straight Fit Corduroy Pants

As long as you go for a straight fit rather than a slimmer or even skinny fit, corduroy pants can be among the comfiest in your arsenal. We’ve long sworn by J.Crew’s version in their 770 fit. Pair ’em with some thick socks and your favorite moccasins, and you’ll be a happy, happy man.

Italian Drawstring Infantry Pant
Italian Drawstring Infantry Pant
Todd Snyder

Todd Snyder Infantry Pant

With its cargo-style pockets, nicely tapered ankles and overall smart tailoring, the Todd Snyder Infantry pant is full of nifty little design flourishes that help elevate it far beyond what you’d expect from a garment with a drawstring waist.

Relaxed Cotton Elasticated Trousers
Relaxed Cotton Elasticated Trousers
Mr P

Mr P. Elasticated Cotton Trousers

Just like with the Uniqlo option above, the key to pulling off the relaxed fit trouser is to make sure it’s on the shorter side and tapered just enough. We can’t have any excess fabric bunching up around your ankles, now can we?

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