30 Men’s Fall Outfit Ideas (Updated for 2019!)

30 Men’s Fall Outfit Ideas (Updated for 2019!)

Upgrade your look for cooler weather
bright bazaar wearing bandana

By Megan Collins | Last Updated: Oct 17 2019 | 10 min read

Looking for men’s fall outfit ideas? Team SG has you covered.

Fall technically started last month, but the weather (here in New York at least) has been fall-like at best only recently. Freezing in the mornings sweltering by lunchtime. What’s a person to do! Bottom line? It can be hard to know what to wear. Loads of light layers? A wool sweater with swim trunks? Trust us, we get it.

We’ve been stocking your closet with fall sweaters and jackets, and now it’s time to inspire you with some full-on cool weather lewks.

And who can’t use a little outfit inspo from time to time? Whether that’s ideas on how to add new pieces to your wardrobe rotation or new takes on wearing the items buried in the back of the closet.

The best part? You can wear denim every damn day (if you really want to). Take that No Jeans January!

Below, 30 men’s fall outfit ideas:

Day 1: Wear something yellow

SG Says: It doesn’t have to be yellow pants, but Michael B. Jordan does make a compelling case for them here.

Day 2: Wear millennial pink

SG Says: We’ve got ideas on how to wear this year-round hue!

Day 3: Wear a suit with sh*t-kicker boots

keanu reeves green suit
Keanu Reeves via @jeanneyangstyle

Day 4: Get your sherpa on

SG Says: We’ve said it before and we’ll say it again: light jackets are what makes fall fall. Take advantage.

Day 5: Wear a bold pattern

kumail nanjiani patterned suit
via GQ

Day 6: Sport a plaid shirt

one dapper street plaid shirt
via One Dapper Street

Day 7: Wear a denim jacket (damnit!)

SG Says: We’re not going to say it again (okay, we’ll probably say it again). Here’s a guide on all the ways to wear one, if that helps nudge you along.

Day 8: Keep things simple with a t-shirt and jeans

chubstr denim jacket
via Chubstr

Day 9: Go monochrome head-to-toe

a.rod monochrome outfit
via @arod

Day 10: Mix dress pants and a leather jacket

Day 11: Try a hat you think you can’t pull off

Day 12: Try (just try) a hip pack

Day 13: Wear the most expensive thing in your closet

matt smith emmys 2018
via Getty Images

Day 14: Sport a suit with a t-shirt

SG Says: Style blogger Leo Chan shows there’s no one way to wear a suit. Here’s a guide on how to make your suits feel more like, well, you.

Day 15: Flash some ankle in cropped pants

noah centineo suit
via Teen Vogue

Day 16: Two words…White. Jeans.

Day 17: Sport some suede

SG Says: You know we’re all about luxe’ing (is that a word?!) up your wardrobe for fall with some suede, corduroy, and more. Henry Golding shows how it’s done@

Day 18: Wear a bandana

SG Says: We’ve been talking about how much we love bandanas on guys since summer, and good news! They’re still very cool for fall…

Day 19: Sport your all-time favorite sneakers

SG Says: Check out a list of our favorite sneakers right now if you need some inspiration.

Day 20: Choose your own adventure: double-breasted suit *OR* some tie-dye. Your call.

tommy hilfiger lewis hamilton
via GQ

Day 21: Wear something you haven’t worn in at least six months

SG Says: Your favorite fisherman’s sweater? A topcoat that might need a dry cleaning? Your call!

Day 22: Sport a sport coat

Day 23: Try a pair of joggers (if you haven’t already)

Day 24: Wear a #tbt t-shirt

julius randle tupac shirt
Julius Randle via @morethanstats

Day 25: Pull on a turtleneck

SG Says: Check out this guide on how to wear a turtleneck this fall and winter!

Day 26: Wear something summery (for the last time this year)

Day 27: Invest in a “statement” coat

nick wooster coat
via The Idle Man

Day 28: Go head-to-toe in denim

Day 29: Wear something *super* outside your comfort zone

asap rocky wearing a purse
via GQ

SG Says: Maybe that’s not a wicker purse and laced jeans like A$AP Rocky (hey, he was at Fashion Week!) but there’s gotta be something in your closet you’ve been nervous to wear.

Today’s the day!

Day 30: Re-wear your favorite look from the month…you made it!


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Ready for an upgrade?

…But dread the thought of shopping for new clothes? Let Team SG shop for you!

We’ve got men’s fall outfit ideas and we’re ready to share them with you. Ready to seriously improve your closet and your confidence? Give us a shout.

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