4 Men's Fall Outfit Tips | How to Elevate Your Style

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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 — images: @steviesalle

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!

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 — images: @1lrg

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.