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3 End of Summer Men’s Outfits You’ll Look and Feel Good Wearing

Look good 'til the fall equinox
men's outfit flat lay of an off-white short-sleeve shirt, brown work pants, a gold cuff bracelet and brown lace-up boots

by Megan Collins Updated: September 2, 2024

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Presented by Huckberry

It’s a tricky time to get dressed. Labor Day weekend hits, and you think, Time to pull out the turtlenecks!, but the weather report says, Or maybe we go to the pool?

If you find yourself fighting this seasonal style push and pull, Team SG is here to help.

End of summer men’s outfits look best when they nod towards both seasons equally. That means: short sleeves with long pants. Cut-offs with a collared shirt. And always? A whole lotta ankle.

Here, find three looks that perfectly fit the end of summer style bill. These outfits deliver on style, and comfort. And best of all? You can find them all in one place, on Huckberry, right now.

So, get ready to conquer the end-of-summer in style. Whether it’s hot as hell or feeling like fall, you’ll look and feel your best.

Keep scrolling for 3 end of summer men’s outfits to wear now…

end of summer men's outfits

Where to wear it: on a date

Shop the outfit:

  • polo shirt: Wills
  • athletic-tapered jeans: Flint and Tinder
  • suede loafers: Astorflex

Perfect for coffee, an afternoon stroll, or a post-dinner cocktail.

Loafers make for an easy way to upgrade any end of summer men’s outfit, like this polo and jeans combo.

end of summer men's outfits, this one features a short-sleeve shirt, work pants, and suede boots

Where to wear it: out with friends

Shop the outfit:

  • heavyweight pocket tee: Flint and Tinder
  • double-knee work pants: Proof
  • cuff bracelet: Miansai
  • boots: Easymoc

You may as well break in your double-knee twill pants now. The workwear trend is just getting warmed up this fall, and this pair from Proof is sure to be in your regular rotation. They’re super-stylish and not so heavy you’ll feel like you’re actually supposed to be working in them.

end of summer men's outfits featuring a long-sleeve oxford shirt and camo shorts

Where to wear it: a Labor Day cookout

Shop the outfit:

  • Oxford shirt: Flint and Tinder
  • camo shorts: Flint and Tinder
  • sunglasses: Huckberry
  • slip-on mules: Luca

There’s very few outfits that every woman finds attractive on a man. A midnight blue tuxedo. The perfect jeans and t-shirt combo. And of course, fall’s most perfect outfit: a long-sleeve shirt with shorts.

Button yourself into your favorite beat-up Oxford, and camo shorts for a shockingly stylish men’s outfit mullet. Business on top, party on the bottom.

***

Presented in partnership with Huckberry. Thanks for supporting the brands that support Style Girlfriend!

More seasonal style stories from SG HQ:

8 Stylish Cardigan Outfits for Men

This is the Secret to WFH Style

Starbucks Says It’s Fall. So We All Have to Dress Like It.

Megan Collins

I started Style Girlfriend to help guys look, feel, and act their best.

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