The Best Summer-to-Autumn Menswear Essentials, According to Our Style Expert

From sunny August days to brisk September evenings, here’s what deserves a spot in your transitional wardrobe.

August is that awkward-but-important sweet spot in every stylish man’s calendar. The sun’s still out, but the fashion calendar is already shifting into fall mode. Stores are clearing summer sales racks and rolling out next season’s stock—but what’s worth buying right now?

According to our menswear editor, the answer lies in transitional pieces: garments that’ll carry you from balmy days to breezy nights without skipping a beat.

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🔥 Short Shorts, Still Hot

Yes, short shorts are still in. While the weather allows, you can’t go wrong with tailored above-the-knee shorts. They’re not just for the beach — pair them with a camp-collar shirt or even a light sweater thrown over your shoulders and you’re dinner-date ready.

Tip: Neutral colors like navy, beige, or olive work well when transitioning to fall. They pair effortlessly with knits and layers.

🛒 [Check out our top picks for men’s short shorts here →]
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👔 Oxford Shirts: Your Layering Hero

An Oxford shirt is hands-down one of the best investments you can make in late summer.

• Warm day? Wear it open over a tank.

• Cool night? Button it up under a light blazer or bomber jacket.

• Traveling? Roll the sleeves and layer it with a knit for in-flight elegance.

Choose soft cotton versions in white, sky blue, or subtle stripes for maximum versatility.

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🧶 Lightweight Knits: Preppy, Practical, Perfect

Don’t overlook a lightweight jumper. Whether it’s a merino crewneck, zip-up polo, or cotton cardigan, these pieces add instant polish—and warmth—without overheating you.

Channel a little Nicholas Hoult energy by casually tying a knit over your shoulders or across your chest. It’s a power move that says: “I’m stylish, and I came prepared.”

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🧥 Layer-Ready Jackets

It might be too soon for heavy outerwear, but now is the right time to pick up:

• Overshirts / Shackets

• Unstructured blazers

• Lightweight bomber or Harrington jackets

These are perfect over T-shirts in August and can be upgraded with scarves or hoodies once October rolls in.

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👖 Trousers That Work Year-Round

Swap your beachy linen pants for cotton chinos or relaxed-fit trousers in heavier twill or canvas. Cropped lengths and pleats are still on-trend, but keep the color palette versatile—navy, tan, olive, charcoal.

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Final Thought: Invest Smart, Layer Smart

This is not the season to blow your budget on deep summer pieces. Instead, think longevity—what can you still wear in October? Look for breathable fabrics, layerable fits, and colors that can move fluidly between seasons.

Whether you’re heading to a rooftop brunch or layering up for your commute, these summer-to-autumn picks will have your wardrobe doing the hard work for you.

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🛍️ Need help finding the best deals or brands?

Check out our curated Summer-to-Fall Menswear Picks – updated weekly.
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