Men’s Fall Fashion Finds for Cooler Weather
The first hint of fall
I Felt a Breeze the Other Day, So Naturally I’m Dressing for Fall
The temperature dropped approximately two degrees, and that was all the encouragement we needed to start looking at sweaters, corduroy, flannel, and every cozy layer we could find.
Was it actually cold outside? Absolutely not.
That first tiny hint of cooler weather always makes fall feel close enough to start planning for—even if Tennessee still has a few aggressively warm afternoons in store.
We gathered men’s fall fashion ideas that can help bridge the awkward gap between summer and actual sweater weather. Think lightweight jackets, textured knits, relaxed pants, and a few warmer layers for when fall finally decides to commit.
For the “It’s Technically Still Warm” Days
Layers you can wear during a cool morning and remove once the sun remembers what state we live in.
Lightweight Bomber Jacket
$39.99
A classic bomber makes a basic T-shirt and pants feel like an intentional fall outfit without adding too much warmth.
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Oversized Vintage-Style T-Shirt
$34.99
The washed finish and oversized fit give this tee a relaxed, lived-in look that works well beneath jackets and overshirts.
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Corduroy Button-Down Shacket
$31.99
Corduroy automatically makes an outfit feel more autumnal. Wear this open over a tee now and button it up once temperatures drop.
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Lightweight Plaid Flannel
$28.99
Nothing announces fall quite like plaid flannel. This is an easy everyday layer for errands, casual dinners, or a night outside.
Shop HereSweater Weather, Whether the Weather Agrees or Not
It may be slightly premature, but the sweaters are already calling.
Quarter-Zip Pullover
$39.99
A quarter-zip feels polished without becoming overly dressy. Pair it with chinos for dinner or jeans for a casual fall outfit.
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Waffle-Knit Crewneck Sweater
$25.99
The waffle texture gives this simple crewneck more personality. It would work with jeans, cargos, chinos, or corduroy pants.
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Classic Cable-Knit Sweater
$43.99
This one delivers the full classic fall look. The cable-knit texture feels cozy and timeless without requiring complicated styling.
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Casual Cable-Knit Pullover
$24.99
A cozy knit at a lower price point. Wear it alone or layer it over a collared shirt when you want to look slightly more put together.
Shop HereThe Fall Pants Rotation
Cooler weather gives us an excuse to bring texture, deeper colors, and roomier silhouettes back into the rotation.
Three-Pack of Athletic Joggers
$39.99
An easy option for workouts, errands, travel, or staying home. The zippered pockets are especially useful while you’re out.
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Wide-Leg Baggy Jeans
$39.99
These relaxed jeans bring a more current silhouette to fall. Pair them with an oversized tee or balance them with a fitted sweater.
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Wide-Leg Corduroy Pants
$29.99
Corduroy provides plenty of fall texture without adding another heavy layer on top. Style these with a tee, quarter-zip, or sweater.
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Relaxed-Fit Stretch Cargo Pants
$31.99
Practical, comfortable, and easy to wear, these cargos work for outdoor projects, casual days, and everything in between.
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Athletic-Fit Stretch Chinos
$22.00
These are for days when jeans feel too casual but dress pants would be doing entirely too much. The athletic fit allows more room through the seat and thighs.
Shop HereFor When It Finally Gets Properly Cold
Eventually that tiny breeze will become actual cold weather. We would rather be dramatically overprepared.
Sherpa-Lined Lightweight Vest
$48.99
A lined vest adds warmth without the bulk of a full winter coat. Layer it over a flannel or sweater for outdoor projects and cool weekends.
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Cotton Slouch Socks
$24.99
Slouchy crew socks are a small way to make an everyday outfit feel cozier. Let them show above sneakers or boots for a relaxed fall look.
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Merino-Wool Hiking Socks
$24.99
These thicker thermal socks are made for cold days, hiking, boots, or anyone whose feet decide it’s winter before the rest of their body does.
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Fleece-Lined Thermal Underwear
$25.99
Excessive for the first breeze of September? Probably. Useful once winter arrives and outdoor chores stop being charming? Absolutely.
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