Stroll Into Fall in Style With Some of Our Favorite Men’s Fashion Pieces for 2020

Two men in fall clothes
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Now that Labor Day has come and gone, we’re finally in full-fall mode even though, well, it isn’t exactly fall quite yet. While we wait for those temperatures to drop, now is the perfect time to go ahead and stock up on pieces that can seamlessly transition you from summer to fall to winter. And you know what that means — long-sleeves, jeans, accessories and layers galore.

Fall is an opportunity to have some fun with fashion. Breach out of your summer uniform (a tee and shorts) and dabble in layering multiple pieces together that you normally wouldn’t. Now’s the chance to play with different kinds of textures, colors and looks to create the ultimate fall ‘fit for apple picking, pumpkin snagging and drive-in movie dates. But if you feel like the whole process of switching up that wardrobe is pretty daunting, don’t worry, we’ve got you covered.

Below, we’ve rounded up 17 of our favorite pieces that you’ll need to have a stylish fall. And, to make it even easier, we’ve scoured the internet for socks, shoes, pants and shirts, to keep you covered — literally — from head to toe. So grab that pumpkin spice latte and settle in for your most stylish fall ever.


1. Everlane Premium-Weight Long-Sleeve Crew

It never hurts to have a clean, reliable basic long-sleeve t-shirt like this offering from Everlane. Black tees go with everything and are super useful to layer under a sweater, jacket or even a sport coat. Made from high-end cotton that feels as rich as it does cozy, it’s bound to be one of your favorites. This long-sleeve tee comes in a range of colors, from this dark black to oatmeal to mauve and more.

Everlane Premium-Weight Long-Sleeve Crew Courtesy of Everlane


2. J. Crew 484 Slim Fit Chinos

Few brands do chinos better than J. Crew, so they naturally deserve a spot on our list. With a cornucopia of colors befitting of fall’s lovely hues (thinking browns, forest greens, and greys), there’s most likely a version here that you don’t already own. The tailored, slim fit also has just a touch of elastic in them, so you won’t need to worry about them being too snug.

J. Crew 484 Slim Fit Chinos Courtesy of J.Crew


3. Uniqlo Color Socks

A good colored sock is a quick and easy way to convey to others that you know what you’re doing when it comes to fashion. Uniqlo has a slew of fall-colored statement socks that aren’t too flashy but add a nice pop to your fall ‘fits. We think these socks rock the best when shown off only minimally with a classic pant-roll/mid-high boot combo. These socks are cheap as it gets too, with pairs only going for $3.90 each. How’s that for an affordable fall outfit additive?

Uniqlo Color Socks Courtesy of Uniqlo


4. ASOS Knitted Scarf

When it comes to dudes rocking scarves, you need to be sure you don’t get anything too gaudy, light or frilly. While plaid might be tempting, this season we’re recommending you try and stay away in case it clashes with your outfit. Anything muted down and dulled-colored in the realm of scarves for men is perfect, so this fall, we’re going with this knitted scarf from ASOS. It’s short in length, dull-ish yet still bright in color and easy on the wallet, which makes for a fantastic scarf option for dudes. It’s knitted too, so this one will keep your neck cozy all fall and winter long.

ASOS Knitted Scarf Courtesy of ASOS


5. Champion Reverse Weave Crew Neck Sweatshirt

Ahhhh, Champion. The absolute GOAT of modern-day athleisure. As the temperatures begin to drop, we suggest you replace your crappy, old crewneck with Champion’s trendy yet casual reverse weave crew for whenever you’re staying comfy at home or running a few errands. Black is a solid choice when it comes to crewnecks, considering it matches with everything, but this handsome sweatshirt also comes in white if that’s your gig. Just watch out for stains!

Champion Reverse Weave Crew Neck Sweatshirt Courtesy of Pacsun


6. Everlane French Terry Sweatpant

Where there’s a sweatshirt, there are also sweatpants. Right now, we’re obsessed over Everlane’s new French Terry sweatpants because of their cozy fit that’s warming yet not overwhelming. We find that a lot of the time, we’re absolutely drenched in sweat when it comes to our classic sweatpants, but the French Terry’s don’t have much fuzz on the inside that trap your legs what feels like a furnace. Instead, the material is thicker, yet still breathable. Out of the four colors available, the pine color looks the most dope with the jogger style, so if you’re going to go with any, go with that.

Everlane French Terry Sweatpant Courtesy of Everlane


7. Nike Killshot 2 Sneaker

These Nikes are bad as hell. But, bad in the way that means cool. You knew what we meant. With an assist from J. Crew stores, these Nike sneakers were the shoes of 2019, and they’re still kicking in 2020. These leather shoes are the perfect everyday sneakers, and they go with absolutely everything. In addition to the navy blue checkmark, you can find updated colorways from Nike for 2020.

What we love about the Nike Killshot 2 is that they’ll look just as good in a casual office setting as they do when you’re running around town on a weekend or out on a date. A perfect low profile sneaker, the various contrasting touches (whether it’s the cripsy gum sole, the suede patches, or that vibrant Nike check) all build to something that’s never too much, opting instead for just the right amount of each part. The final result is a striking looking sneaker that’s perfect to wear all season long.

Nike Killshot 2 Sneaker Courtesy of Nike


8. Topman Jake Classic Bomber Jacket

There’s nothing like a dapper-looking bomber jacket in a neutral fall color. Peep this bomber from Topman that takes the classic style to the next level by incorporating a puffed quilting outer design for a sporty, outdoorsy vibe. The jacket itself is colored in sage, which replicates the time of year where leaves are just beginning to lose their green coloring and transform into their autumnal reds, yellows and oranges. It’s made from 100% polyester and has side welt pockets for holding your valuables.

Topman Jake Classic Bomber Jacket Courtesy of Nordstrom


9. Carhartt Beanie

We said it once and we’ll say it again, beanies are the cherry-on-top to your favorite fall looks. The most handsome beanie on the market is clearly this one from Carhartt because of its easy-on-the-eyes look, a slew of solid colors to choose from and the subtle branding in the front. Keep your head warm when outside or keep in on your head the whole day through to complete your look. The majority of colors are pretty fall-forward, but we’re obsessed with this beanie in orange. But, you can’t go wrong with a classic all-black look either.

Carhartt Beanie Courtesy of Amazon


10. AG Tellis Slim Fit Jeans

A handsome pair of jeans that fit your body just right are a staple for cooler weather, and this year, we’re looking no further than these slim-fit jeans from AG. These babies hit the sweet spot between light wash and dark wash jeans, which is an on-the-nose color for a seasonal transitional period like fall. Because they’re slim-fit in their design, they hug your body right but stay loose enough to both look and feel comfortable on your legs. Pair these with your favorite fall flannel shirt or a Champion crewneck. For these, we definitely suggest you roll the bottoms for that classic cuffed look.

AG Tellis Slim Fit Jeans Courtesy of Nordstrom


11. Herschel Supply Co. Classic Backpack

If you’ve recently headed back to campus, update your backpack that’s falling apart with this one from Herschel Supply Co. Herschel’s got a mad range of colors to choose from, but if you’re looking for something that looks great during any season (with an emphasis on fall) we suggest any lower key, muted color like this navy option. Built with an inner laptop pocket, roomy interior and exterior pocket for smaller necessities like your wallet or gym clothes. If you’re looking for a new college backpack, this modern-day classic will make you the coolest kid on campus.

men's fall fashion 2020 Courtesy of Amazon


12. H&M Fine-Knit Turtleneck Sweater

Turtlenecks are the way to go when it comes to modern-day formalwear. We know a white button-down shirt still looks pretty dope under a suit, but have you tried an off-white turtleneck and a gold chain necklace? Absolutely gamechanger. Believe it. Be the most handsome guy in the room at any upcoming formal fall event you have marked on your calendar. You deserve to look as fly as you are. And at only $25? Why the hell not?

H&M Fine-Knit Turtleneck Sweater Courtesy of H&M


13. Red Wing Moc Toe Boot

Every man needs a classic set of boots — and there are few brands that do it better than Red Wing. Their moc toe boot is a classic menswear mainstay, seen on the likes of Ryan Gosling, and will hold up to all kinds of wear and tear, so they’ll get you a hell of a long way through this fall and winter. Rugged and built to last, they’re a boot you’ll feel just as good about buying as you do wearing them.

Red Wing Heritage 6" Moc Toe Boot Courtesy of Zappos


14. Amazon Essentials Long Sleeve Plaid Flannel Shirt

There’s not a single need to break the bank when looking for a good-looking flannel wear from fall to spring. While the majority of our team typically finds our flannel shirt secondhand at places like Goodwill and Salvation Army, Amazon has a wide variety of affordable options if your local thrift store doesn’t have what you want. When looking for your go-to flannel this season, we suggest you ditch the typical red and black buffalo plaid print and save that for a last-minute lumberjack Halloween costume. Right now, we prefer this green, blue and white option that’s a great fit for fall colors. This will pair well with your favorite fall jeans, a backward snapback and a pair of brown boots.

Amazon Essentials Long Sleeve Plaid Flannel Shirt Courtesy of Amazon


15. ASOS Fingerless Gloves

If you’re the type whose hands chill pretty easily, we suggest you grab yourself a pair of fingerless gloves for fall. There’s no need to go full swing into full-fingered gloves or mittens just yet because it won’t be that cold out, but fingerless gloves are a cool, relatively seasonable way to feet your hands warm without jumping right into winterwear. Tone it down with this black pair from ASOS — they’ll match all your outfits and look great on.

ASOS Fingerless Gloves Courtesy of ASOS


16. Converse Chuck 70 Restructured

Take your go-to summer hi-tops into fall with these wild deconstructed to restructured Chuck 70s we needed to double-take at. These two-for-ones are giving us some serious scarecrow vibes, which is perfect for this time of year. The hi-tops themselves look almost half-assed thrown together, but we can assure you, they’re crafted like any other pair would be. The exterior is simply for aesthetical purposes. Still looking to wear Converse in the fall, but restructured ain’t your vibe? No worries, Converse has a ton of different options to sport this fall.

Converse Chuck 70 Restructured Courtesy of Converse


17. Levi’s Denim Trucker Jacket

Western vibes are absolutely in for this fall, so making sure you have a denim jacket is a must. And while there are plenty of luxury options to splurge on, sometimes it’s best to just shut up and play the hits. With that in mind, this classic Levi’s Trucker jacket is a tough option to beat. Quality, at a price that’s not too overwhelming, makes for an accessible option for nearly everyone. The black color will go with everything you already own, but also don’t be afraid to try a new color like Harvest Gold for a trendy look that is sure to turn a few heads.

Levi's Denim Trucker Jacket Courtesy of Zappos


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