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4 Men’s Fall Outfit Tips (2024)

Smart tricks to look stylish this season
attractive man walking down the street with his hands in his pockets, he's wearing a baseball cap, quilted jacket, dark shirt, and joggers

by Gabi Updated: September 11, 2024

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When it comes to casual fall outfits, there’s a fine line between “Ben Affleck spotted at Dunkin’ Donuts” and “Ben your second cousin who just got fired from Dunkin’ Donuts.”

So, Team SG compiled four tips for guys to ensure your fall ‘fits wind up on the Affleck side of the casual autumn outfit spectrum. 

Check out 4 fall outfit tips to elevate your layered-up looks:

1. ROLL YOUR SLEEVES

man standing outside wearing a black baseball cap, black sunglasses, a black button-down shirt, black pants, and black shoes
images: @steviesalle
close-up of a man in front of a large wall wearing a black hat, black button down shirt, and black pants

Seems simple, right?

That’s because it is!

Whenever you’re wearing extra layers—and in the fall months, when aren’t you?!—fold back your jacket or top layer for a casual, je ne sais quoi vibe.

As for the proper technique? Don’t overthink it.

man with glasses and a beard standing in front of a wooden door wearing a plaid shirt with a grey sweater over his shoulders
@harandoesthings

Whether it’s a worn-in plaid shirt or structured shirt jacket, if it’s got a sleeve that buttons at the wrist, you can fold it back, then shove the bunched-up material up your forearm. Here’s a primer we made about a million years ago that’s still helpful!

RELATED: Shop Team SG’s fall favorites for guys

Besides a rolled sleeve being stylish, this extra layer is functional, too. After all, it’s easier to remove items to cool down than to add what you don’t already have on you.

If you have the choice to be prepared or be cold, why risk it? It’s better to have than to have not. And if you don’t end up needing it, maybe someone else will, and then you’re their hero!

2. WHEN IN DOUBT, FLANNEL OUT

older man sitting at a cafe in Italy wearing a red plaid flannel shirt over a white tee, and light wash jeans
@alessandrosquarzi
man standing on a porch wearing a pair of overalls with a red and green plaid shirt over the top
@jms_hrvy_fits

Meeting friends out after work? Going to a bonfire? Headed to a hayride?! Bobbing for apples? Raking crunchy leaves?!

Whatever iconic autumnal occasion you’ve got on the calendar, a flannel shirt will fit right in. 

Whether you opt for a slim fit style buttoned up under a sportcoat, or a boxy fit open over a tee, a plaid flannel gives any outfit instant fall flair.

Plus, flannels are notoriously ultra soft and cozy, so you can feel like you’re wearing pajamas while looking put together.

3. SAY YES TO WIDE-BRIMMED HATS 

man from the waist up wearing worn-in jeans, a white t-shirt, denim jacket, and wide-brimmed hat
@heymarkavery (Ryan Gosling’s stylist!)
man standing in front of a blue wall wearing a casual fall outfit including a quilted vest and wide-brimmed hat
images: @1lrg
man standing in front of a blue wall wearing a casual fall outfit including a quilted vest, denim shirt, and wide-brimmed hat, holding a tan coat over his shoulder

As the saying goes, every season has its hat.

…Okay, no one says that, but hear me out!

Winter is beanie weather. Spring brings baseball caps. Summer says ‘bucket or chuck it’, and fall cools down just enough—but not too much—for the elusive cowboy hat. 

Crafted from luxe materials like leather and wool, this accessory keeps the sun off your face and doesn’t let your body heat escape from your head, marrying the needs provided by the hats of choice in the two sandwiching seasons. 

You may ask yourself, Do I need to be a cowboy to pull this off? And the answer is absolutely not. 

Every guy can pull off a wide-brimmed hat with a little confidence and the right clothes.

To keep from looking like cowboy cosplay, stick to other sturdy pieces like been-through-the-wringer jeans and a hearty cardigan.

4. FLASH SOME ANKLE AS LONG AS POSSIBLE

young man in glasses standing in front of a desk wearing a chambray shirt with striped carpenter pants and brown leather loafers
@busterthehuman
man sitting in a living room holding a small dog
images: @willhalbert
small brown dog looking up at a man on a couch

It’s easy to default to a tall sock when wearing a boot, but this fall, challenge yourself to flash some ankle a little while longer.

You can wear a low sock (or skip the socks altogether) with a loafer to give off a rakish, devil may care aura that’s very sexy.

Or, throw on a pair of tall socks and cuff your pants for an added flash of personal style.

man sitting on stone steps, holding a coffee mug and wearing a blue chore coat, blue jeans, brown lace-up shoes, and an orange beanie
images: @craigdhammonds
close-up of a man sitting on stone steps outside wearing blue jeans, patterned socks, and brown leather shoes
two men standing in a tall doorway wearing casual, loose-fitting fall outfits
@gigo19
man walking down the street weraing a blue bomber jacket with a black sweatsuit underneath. on his feet he's wearing off-white sneakers and bright green socks
images: @stylesbyslimster
close-up of a man pulling his green socks over the ankles of his black sweatpants

Don’t forget to roll up your pants, or pull your socks over a pair of sweats or joggers, to show off this slick stylish move!

Shop the story:

man from the waist up wearing tan chinos, a striped t-shirt and a light blue chambray shirt open over the t-shirt
FAHERTY
Tried & True chambray shirt, $148
shop now
close-up of a man wearing a navy shirt jacket over a grey sweater
FLINT AND TINDER
waxed shirt jacket, $198
shop now
men's brown cowboy hat
STETSON
Rawlins cowboy hat, $175
shop now
man from the waist down, sitting on a stool, wearing brown workwear pants with white sneakers
ABERCROMBIE & FITCH
loose workwear pant, $80
shop now
close-up of a man in a plaid shirt over a white crewneck tee with black pants
CORRIDOR
dobby weave plaid shirt, $225
shop now
man from the waist down wearing light tan chinos and black loafers
BANANA REPUBLIC
Athletic Traveler Pant 2.0, $110
shop now

***

More Great Fall Style Stories from SG HQ:

  • A Stylist’s Guide to Layering
  • Casual Outfits to Wear This Fall
  • The Light Jackets You’ll Wear All Season
  • 8 Cardigans for Looking Cool and Feeling Cozy

Gabi

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.

More articles by Gabi

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