What to Wear in the Fall: 26 Pieces That Will Help You Look Awesome This Autumn

Dave Bowden

This post may contain affiliate links. (What's this?)

T he late, great Canadian menswear aficionado Harry Rosen once said, “The gentleman prefers fall.”

And who could blame him? While the oppressive heat of summer leaves us with few options for looking good without sweating our balls off, and winter requires thick parkas that cover the rest of our stylish get-ups, fall offers the opposite opportunity:

The slight chill in the air provides the perfect cover for creating layered looks made up of rugged, handsome materials.

Your Fall Style Starter Guide

What to Wear in the Fall for Men Who Want to Step Up Their Style
What to Wear in the Fall for Men
Image via Pinterest

Because fall’s such a great time for guys who want to look and feel good, store shelves get flooded with so many menswear pieces that it’s easy to find yourself facing decision fatigue and not quite knowing what to wear.

So I thought I’d put together a little starter guide outlining the must-have pieces that every guy should have in his wardrobe come autumn.

Below you’ll find a few of my favorite fall staples, each of which contributes to an overall look that’s masculine, stylish and confident.

As always, when choosing links I’ve tried to stick to what’s easily accessible for the majority of guys; I’ve linked to products that you can either find on Amazon, on major websites that ship just about anywhere, or at your local mall, for those who prefer to do their shopping in brick-and-mortar stores.

And if you can’t find these exact products, don’t worry: they’ll still give you a good idea of what to look for at whatever stores you have available to you.

Note: Some of the links below are affiliate links, meaning if you click through and buy something, I might make a small commission.

Coats & Outerwear

Brown or Grey (or Brownish Grey) Blazer

Fall is the perfect time to rock more muted, earthy colors

Look for something in a heftier fabric – think herringbone or wool – and pair it with dark jeans or a darker khaki (see options for both below) for a masculine look that’s a lot more put together than just throwing on a windbreaker.

FLATSEVEN | Herringbone Wool Blazer Jacket (with Elbow Patches) 

Tallia | Tweed Herringbone Sportcoat 

Leather Jacket

Need something heavier than a blazer? The leather jacket is a classic men’s staple in either brown or black. Make sure to keep it fitting snugly in the shoulders, torso, and arms, like the guy pictured above – the last thing you want is a baggy leather jacket that looks like you borrowed it from your dad.

Wantdo | Vintage Stand Collar Faux Leather Jacket

Nordstrom | Calfskin Leather Moto Jacket 

Top Coat (aka Overcoat)

When the temperature starts feeling more “early winter” than “late summer” you’ll want something that covers part of your legs. Even though an overcoat is outwear, look for one that fits similarly to a blazer in order to maintain a sleeker, more sophisticated silhouette.

J.Crew | Crosby Topcoat in Wool-Cashmere 

Southern Gents | Single Breasted Topcoats 

Nautica | 3 Button Wool Blend Topcoat

Lightweight Peacoat

The peacoat is a classic and an absolute must-own for winter, but if you want to rock the same style before the temperature really bottoms out, look for an unlined, lighter weight version. As with the overcoat, keep the silhouette slim.

Match | Men’s Wool Classic Pea Coat (pictured above) 

Levi’s | Wool Classic Double-Breasted Wool-Blend Peacoat 

Trench Coat


An absolute classic worn by everyone from Humphrey Bogart to my stylish-as-hell Italian grandfather. Even if you don’t wear a suit to work, a trench is a great way to make an otherwise mundane outfit look significantly more classic and gentlemanly.

London Fog | Plymouth Twill Belted Double-Breasted Trench Coat 

ASOS | Shower-Resistant Double Breasted Trench 

Must Have Shoes for Men Want to Out-Dress the Other Guys?

The (handsome) devil is in the details.

Enter your email address below to discover the 9 Details You Need to Nail.

I will never send you spam. Unsubscribe at any time.

Shirts & Sweaters

Shawl Collar Cardigan Sweater

Leave it to James Bond to show you exactly how to wear a shawl collar cardigan

Welcome to your fall uniform. Find a shawl collar that fits as well as Daniel Craig’s does here, pair it with dark jeans and a hearty leather belt like he does, wear the shit out of it all fall, then layer a coat over top to keep rocking it straight through winter.

Amazon – All Brands

Vincenzo Boretti | Chunky Knit Shawl Collar Cardigan 

Chambray/Denim Shirt

Need something to layer under that shawl collar sweater when it gets cold? The texture on a denim (or lighter weght and better-for-layering chambray) shirt is perfect for fall—with or without the sweater.

Goodthreads | Slim-Fit Long-Sleeve Solid Oxford Shirt

J.Crew | Indigo Japanese Chambray Shirt

Long-Sleeve Henley

The preferred shirt of Hollywood leading men and regular guys alike, a henley is a cross between a regular t-shirt and a polo. Something about those three or four buttons at the top just make it look masculine and stylish, and the long sleeve version will come in handy when the temperature starts to drop.

FLATSEVEN | Casual Henley Shirt with Button

H&M | Henley Shirt 

Old Navy | Thermal Henley for Men 

GAP | Long Sleeve Indigo Henley 

Rugby Shirts

A stylish alternative to a hoodie. Look for one with broad stripes, like this model from Land’s End, or a solid color with a contrasting (usually white) collar.

Front Row | Long Sleeve Sports Rugby Shirt

L.L. Bean | Lakewashed Rugby 

GAP | Chest Stripe Rugby Shirt

V-Neck Merino Wool Sweater

A classic men’s staple that looks as good layered under a blazer or topcoat as it does on its own. I’ve written at length about how the perfect v-neck should fit, but as a rule of thumb remember to keep it slim and look for a “V” that doesn’t dip down too low.

Uniqlo | Merino Wool V-Neck Sweater 

J.Crew | Merino Wool V-Neck Sweater 


Dark Green Jeans or Khakis

You can get away with pastels and lighter shades during the summer, but autumn is the time to break out darker, more masculine shades. A deep green like the one pictured above is a perfect hue for the fall.

Match | Slim-Tapered Flat-Front Casual Pants 

Dark Blue Jeans

Every shirt, sweater and piece of outerwear mentioned above looks great – and maybe even best – when paired with a dark pair of denim.

J.Crew Factory | Sutton Jeans in Dark Rinse

Levi’s | 513 Slim Straight Jean

J.Crew | 484 Slim-Fit Stretch Jean in Indigo

Thin   Waled   Corduroys

With corduroy pants, the key is to keep the wale – which is the name given to the ribbing that defines corduroy – nice and thin. The added texture gives cords a look that’s perfect for fall, while the added weight keeps your legs warm.

Levi’s | 511 Slim Fit Corduroy Jean 

J.Crew Factory | Driggs Cord

Dockers | Jean Cut Stretch Straight Fit Pant

Dark Beige Khakis

As the leaves on the trees start to turn darker and more rustic-colored, so should your khakis. Look for colors with hues of red, orange and brown – the color of rust, basically – and pair them with sweaters or jackets in deep shades of contrasting colors like blue or green.

J.Crew | 770 Straight-fit Pant in Stretch Chino

Match | Athletic Fit Straight Leg Casual Pants

Shoes & Boots

Leather Boots

Easily one of my favorite things about fall is the chance to break out the boots. A sleek pair of leather boots with a good toe shape can give you all the refinement of well-shaped shoes, while the extra leather on an ankle-length boot adds an extra dose of ass-kicking.

Johnston & Murphy | Karnes Cape Toe Boots (pictured above)

Kunsto | Leather Lace up Classic Brogue Boots

Levi’s | Lex II Lace-Up Boot

Bruno MARC | Classic Cap Toe Vintage Laced Up Boots

Hearty Brogues


Don’t want to rock a full boot? Opt for a brogue with strong rubber soles that will protect your feet from puddles and add a shit-kicking motif to your look.

Clarks | Men’s Montacute Wing Oxford Shoe 

Bostonian | Melshire Wing Lace Up Dress Oxford

Johnston & Murphy | Myles Wingtip

Suede Desert Boots

Also called Chukkas, desert boots were the preferred casual kicks of Steve McQueen and a host of other style icons. Perfect with jeans, khakis and just about every other type of fall-appropriate pant.

Timberland | EK Brook Park Chukka Boot 

Johnston & Murphy | Copeland Chukka 


A Substantive, Leather-Band Watch

While my love for the Timex Weekender is well known, I have to admit that come fall I’m ready to return to the feeling of leather wrapped around my wrist. Look for one that will pair well with the leather in your belt and shoes, and remember to always keep it in the same color family: if you mostly wear brown shoes, go for a brown watch and belt. If you mostly wear black… well, you get the idea.

Seiko | SNDC31 Classic Stainless Steel Chronograph Watch 

Tommy Hilfiger | ‘SPORT’ Quartz Gold and Leather Casual Watch

Ted Baker | ‘TRENT’ Quartz Stainless Steel and Leather Casual Watch

Knit Ties

Fall’s all about thicker, warmer textures, and a knit tie pairs perfectly with the tweeds, cottons and wools of your other clothes.

Tommy Hilfiger | Men’s Solid Knit Slim Tie 100% Silk

The Tie Bar | 100% Knitted Silk Tie

AngelShop | Vintage Smart Casual Mens Solid 2″ Skinny Knit Tie

Wool Socks

There are few better feelings in the world than sliding your cold feet into a warm – and seasonally stylish – pair of thick wool socks. (Although sliding said sock into a stylish leather pair of boots comes a close second.)

PureAthlete | Midweight Ski Socks

Ueither | Vintage Style Wool Warm Crew Socks

Maggie’s | Organic Wool Killington Mt. Hiker Socks

Leather Gloves

When the weather really starts to drop, wrap your hands up in style. Keep your gloves in the same family as your belt/shoes/watch, and remember to size down: you want gloves to fit snugly like the ones pictured here, not flap off your fingers.

CASF | Men’s Warm Lambskin Genuine Leather Gloves (pictured) 

Harrms | Best Touchscreen Nappa Genuine Leather Gloves

Anccion | Touchscreen Texting Winter Leather Gloves

Lighter Weight Scarf

Guys tend to shy away from scarves until the weather really requires them.

That’s a damn shame, because men you learn how guys can wear a scarf with style, you quickly find that it’s an easy way to add a roguish bit of flare to your look, while still looking masculine as hell. Take a cue from the picture above and pair one with a blazer or lighter weight jacket.

Bonobos | Lightweight Wool Scarf

FULLRON | Winter Cashmere Scarf

Alternative | Printed Oversized Bundle Up Scarf

Ray Ban Wayfarers

Step 1: Pick up a pair of Ray Ban Wayferers in black or tortoiseshell brown. Step 2: Wear them like Jake Gyllenhaal is here. Step 3: Do literally everything else Gyllenhaal is doing in this picture, which you can see in full here, because he’s killing it.

Ray-Ban | New Wayfarer Classic

Newsboy Cap

The preferred headgear of Ryan Reynolds (pictured here), Brad Pitt, Jon Hamm and countless other Hollywood leading men, the newsboy cap is a great way to look casual and cool (while, ironically, keeping your head warm).

Wonderful Fashion | Classic Herringbone Tweed Wool Blend Newsboy Ivy Hat

Epoch hats | Linen Flat Ivy Gatsby Summer Newsboy Hats

Gamble and Gunn | ‘Shelby’ Newsboy Grey Herringbone Cap

Facial Hair

Alright, fine: so facial hair isn’t an “accessory,” per se. But sporting a little scruff always makes you look more masculine, especially when paired with fall’s warmer and more rugged fabrics.


Consider keeping your razor in the medicine cabinet this season and switching to an electric razor instead. I’ve been using this one from Wahl for years and love the way it leaves the perfect amount of stubble after each shave.

A Longer Hair Style

Not only should you consider giving your razor a rest come fall, but your barber, too (although he or she will probably not be thrilled to hear me say that).

If you’ve ever thought about letting your hair grow out, now’s the time to experiment. Longer hair looks great both on its own, and under warm weather hats like the aforementioned newsboy cap or a knit winter hat (which here in Canada we call by its proper name, a toque).

Must Have Shoes for Men Want to Out-Dress the Other Guys?

The (handsome) devil is in the details.

Enter your email address below to discover the 9 Details You Need to Nail.

I will never send you spam. Unsubscribe at any time.

More Style Advice from Irreverent Gent: