4 Subtle Ways to Upgrade Your Fall Style

4 Subtle Ways to Upgrade Your Fall Style

Smart tricks to look stylish this season

By Gabi Meyers | Last Updated: Oct 30 2023 | 4 min read

sponsored content created in partnership with Huckberry

When it comes to casual fall outfits, there’s a fine line between “Ryan Gosling at the airport” and “Ryan, your second cousin who comes straight to family functions from his construction job at the airport.”

So, together with our pals at Huckberry, we compiled four tips for guys to ensure your fall ‘fits wind up on the Gosling side of the casual autumn outfit spectrum. 

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

1. Roll Your Sleeves

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.

Whether it’s a shirt or 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 all Team SG’s fall favorites

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

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 

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

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.

Wearing a low sock with a boot gives off a rakish, devil may care aura that’s very sexy.

Don’t forget to cuff the pants to show off this slick stylish move!


We’re teaming up with Huckberry this fall to help guys upgrade their cool weather wardrobe. Thanks for supporting the brands that make Style Girlfriend possible!

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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.