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I love a man in a stylish fall ‘fit. Mostly because I just love fall.
It’s got my favorite holiday (Halloween), and the layers? Truly, I’d be happy to throw out every swimsuit I own if it means I can break out my light jacket rotation.
Embarrassing or not, that is just a taste of how passionate I am about autumn.
Plus, my favorite color is orange, so you know I am finding every excuse to wear those pumpkin tones right now. My cornucopia-colored wardrobe makes much more sense in fall.
And did I mention the jackets?? I hope you’re as excited as I am for a bomber/shacket/sweater vest season.
Bottom line? If I can layer it, I am wearing it. And guys, it’s time you do the same with your seasonal menswear rotation.
Need some outfit inspo? Wondering what’s in style now?
Team SG’s got you.
Whether you’re looking for the best cool casual fall outfits or the ideas for going out outfits, we’ve got you covered.
We rounded up a month’s worth of easy men’s fall outfits to wear right now. Below, find some outfits to wear right now and style ideas already put together for your, courtesy of our team.
Below, check out 30 men’s fall outfits to wear right now:
Day 1: Slide into some clogs
Wear it well: Ready to embrace cozy season?
Do it in a pair of slip-on Birkenstock Boston clogs. The iconic fall footwear deserves a spot in every well-dressed man’s repertoire this year. (Bonus points for topping off your look with a beanie.)
Shop the trend
Day 2: Sport a funky jacket
Wear it well: Chore coat that’s not your standard blue? Check. Still-stylish in 2025 workwear pants? Check check.
An easy outfit to copy from head to toe. Literally.
Day 3: Wear athleisure everywhere
Wear it well: The athleisure trend is no longer a trend. And when it comes to the best casual outfits for guys in the fall, pairing shorts with a sweater is an athleisure style level-up.
RELATED: Why Shorts and a Long-Sleeve Shirt is the Perfect Fall Outfit
You could wear your shorts with loafers if you want to go more trendy. Or, if you’d rather keep things a little more timeless, opt for your favorite sneakers or a pair of moccasins.
Day 4: Swap your lace-up boots for cowboy boots
Wear it well: Cowboy boots have been a trend on the women’s side of fashion for a few years now, and I say it’s high time guys got on board.
RELATED: 5 Days, 5 Ways: Cowboy Boots
No, you won’t look like you’re doing Yellowstone cosplay, so long as the rest of your outfit gives off a city vibe.
Day 5: Sport a sweater in a sunny color
Wear it well: Dare I say yellow is the new black?
Sure, neutral-hued sweaters like tan, navy, and black may dominate your closet, but as the temperatures drop, consider adding some sunshine to your fall and winter wardrobe. Butter yellow may be trending, but feel free to let your light shine with something bright if it suits you!
Shop sunny style
Day 6: Hit the streets in classic sneakers
Wear it well: A new season may just be hitting, but classic sneakers are never out of style.
Truly, this is a timeless look!
Whether you go for colorful Vans, a pair of Nike Air Maxes, or high-top Converse, pick a pair of can’t-miss sneakers this autumn.
Day 7: Wear shorts as long into fall as possible
Wear it well: I’m telling you, the fall equinox does not mean that shorts season has to end!
RELATED: Shop our favorite 5″ shorts
Feel free to wear your shorts through the fall season. On chillier days, simply opt for a long sleeve pocket tee, cotton sweater, or your favorite lightweight hoodie.
Day 8: Mix business casual with flat-out casual
Wear it well: I love a denim jacket paired with dressier slim-fit trousers. It’s such a fun mix. You look put together, and still feel totally comfortable.
The shoes you wear will cement which side of the casual-to-dressy continuum you land on. Finish off the look with casual sneakers, and the overall effect will be breezy cool. Go with a more formal shoe like a lace-up or loafer, and you’ll easily be able to pull off the outfit at the office.
Day 9: Add a cardigan
Wear it well: Wearing a cardigan as a top layer instead of a sweater or fleece you pull over your head is such an easy style upgrade for guys to make. There’s no reason not to try it!
RELATED: The 8 Best Men’s Cardigans to Wear Now
Wear yours with loose jeans and a crossbody bag for an outfit that’s totally trend-forward.
Day 10: Top things off with a vest
Wear it well: A hoodie and chinos? Easy.
Adding a quilted vest? Things just got interesting.
It truly cannot get much easier than adding one light-weight extra layer to an everyday outfit to make you look like a style star in your daily life—not to mention the extra warmth when a chilly breeze blows.
Day 11: Go black & blue
Wear it well: Black and blue is an underrated color combo for fall.
Whether it’s business casual or weekend athleisure, level up a fall outfit simply by combining this understated, stylish pairing.
Day 12: Add an accessory…or two…or three
Wear it well: I’ve said it once, I’ll say it again, embrace everyday accessories!
The way to level it up in your men’s fall outfits? Layer your accessories, whether that’s a necklace, bracelet, or rings for a cool way to upgrade any autumn outfit.
Shop accessories
Day 13: Go full English countryside gentleman
Wear it well: Grab your walking stick! Break out your Barbour! It’s time to layer up like this gentleman who looks ready to ramble straight off the sidewalk and into some flat countryside.
Day 14: Go for a relaxed fit with your pants
Wear it well: Don’t be afraid to rock the latest trend with almost-obnoxious ease.
The past few years skinny silhouettes ruled, but this fall is your time to get the circulation back in your legs because the best clothes to wear in fall are the ones you feel most comfortable in.
Meaning? Right now, wear slightly baggy pants in place of your skinny jeans. Your thighs will thank you.
Day 15: Embrace your inner teen in Doc Martens
Wear it well: You don’t have to be a rebellious teen to pull off Doc Martens anymore.
The clompy boots are a big trend for both men and women this fall, so turn up Olivia Rodrigo on your Airpods and get ready to do some serious adolescent brooding. We especially like how they look with smart tailoring.
Day 16: Add a bandana
Wear it well: The humble bandana on its way to becoming a bona fide men’s style essential.
If you haven’t already, it’s time to add one to your closet and wear it with everything. This accessory looks great with everything from long-sleeve shirts to your favorite crewneck sweater—so don’t hesitate to tie one on.
Day 17: Wear a leveled-up chore coat
Wear it well: Dare I say the easiest light outerwear to style, the humble chore jacket looks good over everything in your closet. Yes, really.
No, it doesn’t have to come in such a bold pattern with a bright red collar, but if you already have one in navy or tan, why not branch out?
Shop chore coats
This kind of coat looks good with almost every casual fall piece in your closet, from jeans to chinos to cords.
Day 18: Just add corduroy
Wear it well: Once pumpkins start showing up as decoration on neighbors’ doorsteps, it’s time to break out your favorite cozy fall fabrics.
Corduroy pants make for a great starting point. Also corduroy overshirts, corduroy trucker jackets, and even full corduroy suits.
Day 19: Try a timeless knit polo
Wear it well: A stylish sweater in a neutral color with navy trousers be the easiest look to copy—and look really freaking handsome in—this fall.
Day 20: Top things off with a statement jacket
Wear it well: Bright orange and teal leopard-print statement jacket wasn’t on my shopping list for you this fall, but maybe it should be??
This fun, striking jacket shows that the best fall outfits for guys are the ones that make you feel comfortable and cool. A great jacket usually helps you check both these boxes.
Day 21: Skip the tie
Wear it well: Blazers really can elevate anything, even your favorite jeans and canvas sneakers.
When you’re looking for men’s fall outfits that look dressed up without feeling stuffy, this is a great option.
Replace your button-down and tie with a fitted sweatshirt. You’ll still look professional, just not like everyone else.
Day 22: Mix your neutrals
Wear it well: Basic colors don’t have to be boring. The trick is in adding contrast and unexpected elements. Black jeans in a wide-leg style. A grey cardigan in a cozy knit. Gum sole sneakers that draw the eye.
Day 23: Wear a double-breasted blazer
Wear it well: One way to look like you didn’t just “throw on” an outfit?
Mix suiting separates.
A double-breasted blazer with jeans is not a look you pull off the chair in the corner of your bedroom where laundry goes to be ignored.
Day 24: Hang onto summer in short sleeves
Wear it well: Just because summer is “over” doesn’t mean the weather is going to cooperate with that idea. So on those warmer fall days break out your short sleeve shirts. It’s not worth breaking a sweat to abide by the fall fashion “norms.”
You’ll look and feel cool. I promise.
Day 25: Add a Western belt
Wear it well: This subtle accessory is still very in for 2025.
A belt makes every outfit look better, while a Western belt makes every outfit look cooler.
Day 26: Wear black and brown together
Wear it well: Somewhere down the line wearing black and brown together was deemed a fashion no-no.
I am here to say DO IT! I know the colors are in your closet, and I say wear them together. An easy start? Brown wool trousers and your favorite black tee.
Day 27: Tie on a bolo tie
Wear it well: It’s time to rethink your accessories for this year’s men’s fall wedding guest outfits. If you’re looking for cool-dress up options for guys? Look no further than the bolo tie.
Channel your inner John Wayne like podcast host Pablo Torre, and try swapping your standard neckwear for this Western style instead.
Day 28: Embrace cozy plaid
Wear it well: What says “Let’s hit the pumpkin patch” more than a bright green plaid overshirt?
A cozy top layer like this will come in super-handy, all season long.
Shop plaids
Day 29: Dress in fall colors
Wear it well: When we say “men’s fall outfits,” this is pretty much exactly what we’re talking about.
Besides, it would not be fall if I didn’t tell you to wear fall colors this season.
Think: Thanksgiving cornucopia when you are choosing the colors you should be adding to your fall wardrobe. If it’s not on your Thanksgiving table spread, save the color for next season.
Day 30: Go with a high waist
Wear it well: Hello I love Fair Isle sweaters SO MUCH.
You don’t have to wear yours so…professor at a small liberal arts school on the east coast like above. All I’m saying is..wear this style of sweater this fall! And winter!
More men’s fall stories from SG HQ:
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