Men's Fall Fashion: The 2024 Hit List

a green plaid shirt. text on-screen reads: if you buy one thing this fall...make it a plaid shirt

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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 2024, 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:

men's casual fall outfit with a green plaid shirt, brown t-shirt, black jeans, white converse sneakers, and a silver necklace. text on-screen reads: men's fall outfits (style girlfriend)

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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 chain necklace that sits right below the collarbone elevates the overall outfit for a fall look that really pops.

Men’s Fall Fashion Staple #2

men's green plaid shirt and brown workwear pants. text on-screen reads: if you buy two things this fall, make them a plaid shirt and workwear pants

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 workwear pants to your weekly rotation, like this pair from Proof.

How to wear them:

men's fall outfit with a plaid shirt, work pants, denim jacket and Birkenstock clogs

SG Says: Wear your workwear pants with a textured sweater for a casual office, a long-sleeve tee for WFH, or a cozy flannel for Gilmore Girls cosplay on the weekends.

Men’s Fall Fashion Staple #3

green plaid shirt, brown workwear pants, and dark brown wallabees. text on-screen reads: if you buy three things this fall, make them a plaid shirt, workwear pants, and wallabees

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 Wallabees for fall 2024.

How to wear them:

casual men's fall outfit with a green plaid shirt, brown work pants, cream fleece zip-up jacket, and brown wallabees. text on-screen reads: men's fall outfits (style girlfriend)

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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.