3 Men’s Fall Fashion Staples: The 2023 Hit List

3 Men’s Fall Fashion Staples: The 2023 Hit List

With stylish men's fall outfit ideas
2023 men's fall fashion trends

By Gabi Meyers | Last Updated: Sep 17 2023 | 4 min read

sponsored content created in partnership with Huckberry

I’m about to say something controversial, but there’s a chance you actually have enough clothes. So many, in fact, that when you open your closet on a brisk September morning, you don’t even know where to start to achieve a stylish men’s fall fashion look. But don’t fret. Because I have discovered a solution.

I find that sprinkling in a few fresh items each season makes getting dressed easier, and even more fun, because you get excited to plan outfits around these new, hero pieces.

So, I made you a list.

Below, you’ll find the top three men’s fall fashion staples to add to your closet in 2023, in descending order of the impact they’ll make to your cool weather wardrobe. And yes, of course you’ll find outfit ideas for how to wear them, too!

Men’s Fall Fashion Staple #1

Maybe when pulling your cold weather pieces out of storage, you find your favorite plaid shirt just a little too frayed. Or a buffalo sauce stain attained during last year’s college football season has set in an unfortunately visible place.

Whatever the reason, when it comes to men’s fall fashion, you really need a plaid shirt you love and actually want to leave the house wearing.

This Corridor shirt is that plaid shirt.

How to wear it:

shirt | pants | t-shirt | boots | hat | necklace

SG Says: A flannel shirt in plaid will always have a place in your fall wardrobe, but this twill style adds a fresh, new texture to your cool weather closet.

It’s not too far of a departure from your standard long-sleeve button-up, so wear it just like your other casual shirts. Think: open over a tee, waffle-weave thermal or wife pleaser, or buttoned almost all the way up.

An understated accessory like a silver necklace that sits right below the collarbone elevates the overall outfit for a fall look that really pops.

Men’s Fall Fashion Staple #2

Pants are an easy place to get lazy with your fall style.

Should I wear jeans today? Or…jeans?

So, make the move now to do something different this season. Add a pair of 5-pocket corduroy pants to your weekly rotation, like these Flint and Tinder pants available from Huckberry.

How to wear them:

men's casual fall outfit

shirt | pants | cardigan | boots | sunglasses | belt

SG Says: Wear your corduroy pants with an oxford shirt and tweedy blazer for work, a sweater for date night, or a flannel for Gilmore Girls cosplay.

Men’s Fall Fashion Staple #3
men's fall fashion trends 2023

Is it possible your best boots have seen their best days? If the leather is pulling away from the sole in a way that even your cobbler says can’t be fixed, consider tapping in these Clarks Wallabee boots for fall 2023.

How to wear them:

men's fall looks 2023

shirt | pants | boots | blazer | watch | cuff

SG Says: Wondering how to wear a Wallabee when you’re used to a more standard laced boot? Don’t be.

This shoe blends your go-to chukka with a moccasin vibe for an easy-to-slip-on shoe that works with sweats to chinos and every casual pant in between.

More Men’s Fall Fashion Stories from SG HQ


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!

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.