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 that are as rugged as they are dashing.
The Full Guide to Men’s Fall Style
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 fall menswear pieces that every guy should add to his wardrobe come autumn.
Below you’ll find a mix of timeless fall staples and some newer fall fashion trends, each of which contributes to an overall look that’s masculine, stylish and confident.
Table of Contents
- Men’s Fall Coats & Outerwear
- Men’s Fall Sweaters & Shirts
- Men’s Fall Pants
- Men’s Fall Shoes & Boots
- Men’s Fall Accessories
Men’s Fall Fashion Guide for 2020 (and Beyond)
A Round Up of the Most Essential Men’s Fall Fashion Must-Haves
Men’s Fall Coats & Outerwear
Brown or Grey (or Brownish Grey) Blazer
Look for something in a heftier fabric – think tweed, herringbone or wool – and pair it with dark jeans or a darker khaki (learn more about both below).
This is a classic, masculine combination that’s a lot more put together than just throwing on a windbreaker, and gives you a casual look you can wear pretty much anywhere.
(Not sure why I chose “windbreaker” as my example there. This isn’t the 90s, and you’re not AC Slater. [Wait, you’re not, are you? Because it would be really cool if Mario Lopez read my blog…])
Where to Get Men’s Fall Blazers:
Need something heavier than a blazer?
The leather jacket is a classic men’s staple in either brown or black.
Keep your leather jacket fitting snug, like Bradley Cooper’s does here (and feel free to pair it with a slick pair of aviators to up the bad-ass quotient even further).
To be a little more specific, make sure that it fits nice and snugly in the shoulders, torso, and arms, like the guy pictured here.
Snug leather jackets make you look like a man; loose, baggy leather jackets make you look like a little boy who raided his dad’s closet.
Where to Get Men’s Leather Jackets:
Top Coat (aka Overcoat)
When the temperature starts feeling more “early winter” than “late summer” you’ll want something that covers not just your upper body, but part of your legs as well.
Enter the topcoat, one of the most dashingly handsome pieces of men’s outerwear of all time.
Even though an overcoat is outerwear, look for one that fits similarly to a blazer in order to maintain a sleeker, more sophisticated silhouette.
When buying a topcoat, ask yourself this one question: will you be wearing the coat overtop of a suit jacket or blazer, or in place of one?
If you intend to wear the coat over top of another jacket, opt for one that’s one or two inches bigger in the chest than your jacket size. (So if you normally wear a 40R jacket, try a 42 in the coat.)
But if you don’t wear a lot of blazers and you intend to wear the coat over top of a shirt or sweater (like in the picture above), get one in the same measurements as your jacket, so that it fits snug and cuts a strong silhouette.
Where to Get Men’s Topcoats:
The peacoat is a classic and an absolute must-own for winter, but it can also come in pretty hand in the fall (particularly if you live in a more northern locale, where the fall can get quite cold).
As with the other coats mentioned above, you want to keep the silhouette slim. And for the love of god fellas, if you only remember one thing from this post, please, remember this:
Unlike the topcoat, the peacoat is not meant to be worn over top of a blazer or suit! Instead, think of it more as a replacement for a blazer, albeit it a warmer one.
Opt for one in a classic color like navy, black or grey, which pairs well with all of the essential men’s pants colors and will help you elevate your fall casual style.
Where to Get Men’s Peacoats:
Trench coats are a more mature look, but an absolute classic one, worn by everyone from Humphrey Bogart to my stylish-as-hell Italian grandfather.
The classic move is to throw your trench over a suit to protect it from the rain.
Of course, most of us don’t wear suits very often anymore, but we can still leverage the “dressed up” reputation of the trench to make an otherwise mundane outfit look significantly more classic and gentlemanly.
Where to Get Men’s Trench Coats:
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Men’s Fall Sweaters & Shirts
Shawl Collar Cardigan Sweater
Welcome to your fall uniform.
Find a shawl collar sweater that fits as well as Daniel Craig’s does here.
Pairing it with dark jeans, a henley and a hearty leather belt like he does here is always a safe go-to look, and one you can wear the shit out of all fall.
When the weather starts to get cooler, layer one of the coats mentioned above over top to keep rocking the shawl collar straight through winter.
Where to Get Men’s Shawl Collar Sweaters:
Need something to layer under that shawl collar sweater when it gets cold?
The texture on a denim (or lighter weight and better-for-layering chambray) shirt is perfect for fall—with or without the sweater.
One word of warning when it comes to these shirts: if you’re wearing it with jeans, try to pick a shirt color (or at least a shade) that’s different from the denim you’re wearing down below.
Personally, one of my favorite go-to looks for fall is jet black jeans, a medium blue denim shirt, and a pair of grey chukkas.
Where to Get Men’s Chambray Shirts:
The preferred shirt of Hollywood leading men and stylish regular guys alike, a henley is sort of a cross between a regular t-shirt and a polo.
Like a tee, it has a regular crew neck, as opposed to the more formal collar of a polo shirt.
But like a polo, it has three or four buttons at the collar, allowing you to leave the top one or two undone for a look that’s a little more roguish than a regular tee.
I can’t quite put my finger on why, but there’s something about those three or four buttons at the top that just make henleys look more masculine and stylish then regular tees.
And the long sleeve version will come in handy when the temperature starts to drop.
Where to Get Long Sleeve Henleys:
Rugby shirts are one of the best ways to work athleticwear into your everyday wardrobe.
A rugby shirt makes for a more stylish – but just as comfortable – alternative to a hoodie.
In addition to evoking one of the most bad-ass sports on the planet, the rugby shirt’s collar and similarity to a long-sleeve polo give it a certain refinement that other athletic-inspired pieces usually lack.
The most classic version comes in navy blue with a plain white collar, but you can usually find them in a lot of other colors that work well with the rest of your fall wardrobe, including deep greens, burgundy and brown.
Where to Get Stylish Rugby Shirts:
Merino Wool Sweater
A classic men’s staple that looks as good layered under a blazer or topcoat as it does on its own.
Merino wool sweaters come in two main varieties: v-neck, which is self-explanatory, and crew neck, which many guys would basically call “normal.”
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.
You can find v-neck sweaters in a lot of fabrics, but I favor merino wool because it’s simultaneously lightweight (making it perfect for layering over shirts and under jackets), while still providing a lot of warmth.
To keep yours fitting trim, look for one that has a bit of stretch, and consider sizing down so that the sweater hugs your torso rather than bulging out around the stomach. (I don’t know about you, but I have enough stomach bulge without my sweater adding to it, thank you very much.)
Where to Get Mens Merino Wool Sweaters:
Men’s Fall Pants
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.
When I wrote my roundup of the best men’s pants colors, I included Forest Green as a Good-to-Have color, as opposed to a Must-Have.
But come fall, I think you should really consider dark green pants more of a “must.”
They not only evoke the darker colors that you see in nature throughout autumn, but also provide a great alternative to the standard blue and black that most guys favor in jeans.
Where to Get Dark Green Pants:
Dark Blue Jeans
And speaking of standard colors, a trim-fitting pair of dark blue jeans isn’t just a fall standard.
Come fall, it’s the gold standard.
Every shirt, sweater and piece of outerwear mentioned above looks great – and maybe even best – when paired with a dark pair of denim, as do each of the fall footwear items listed below.
Invest in a couple good pairs of dark blue jeans and you can (stylishly) wear the hell out of ’em all fall and winter long.
Where to Get Men’s Jeans:
Thin Waled Corduroys
Once upon a time, corduroy got a bad rap for being the favored fabric of stodgy old men.
But like a lot of things in the world of menswear, it was reimagined and reborn in the mid-00’s and given new life in the wardrobes of stylish-but-sophisticated guys who want to put a more modern spin on classic materials, patterns and styles.
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 well into winter.
Where to Get Men’s Corduroys:
Dark Beige Khakis
In the summer, light beige (and lightweight) khakis compliment the pastels and lighter shades of blue and green that you wear in your polos.
But 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 colors of fall leaves, basically – and pair them with sweaters or jackets in deep shades of contrasting colors like navy blue or forest green.
The “chestnut” color of the Bonobos khakis featured here is pretty much perfect because it’s more brown than beige, but still very much in the “khaki” family.
Where to Get Men’s Khakis:
Men’s Fall Shoes & 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.
There are multiple types of boots you could consider, which I’ve outlined at length in my roundup of the best casual boots to wear with jeans.
But no matter which style you opt for, having at least one go-to leather boot in your fall wardrobe is an absolute must.
Where to Get Leather Boots:
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.
Also known as wingtips, brogues come from the tradition of hunting parties in Britain, when men would leave their patent leather dress shoes at home to go slosh around in the woods, shotgun firmly in hand.
That’s both one of the most autumn and the most awesome origins I can think for a shoe, which is one of the reasons why brogues ranked high on my list of the best men’s casual shoes (and why you should absolutely add a pair to your wardrobe).
Where to Get Brogues:
Suede Desert Boots
And with good reason. Perfect with jeans, khakis and just about every other type of fall-appropriate pant, chukkas are an easy go-to boot that you can just about anywhere.
One of the reasons desert boots work so well for fall is that they’re relatively streamlined. It’s possibly to find chukkas with the a thick rubber sole and lots of tread, but most have a fairly thin sole that keeps them looking sleek and stylish.
Where to Get Suede Chukkas:
Men’s Fall Accessories
Leather Messenger Bag or Briefcase
The exact style of bag you choose will vary depending on your job, your budget and the look you’re going for.
But whether you wear a messenger bag, a briefcase or even a backpack, you can’t go wrong with a hearty, masculine and classic-looking leather bag.
And, ideally, you’d actually have not one, but two. Keep in mind that when it comes to leather accessories, the stylish man’s rule of thumb is to keep his leathers in the same color category.
If you’re wearing brown shoes, then your belt, watch strap and bag should all be brown as well. Wearing black shoes? Well, you get the idea.
Where to Get Men’s Leather Bags:
A Substantive, Leather-Band Watch
But even I have to admit that, come fall, I’m ready to return to the feeling of leather wrapped around my wrist.
As mentioned above, 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.
Where to Get Leather-Band Watches
There are few better feelings in the world than sliding your cold feet into a warm – and seasonally stylish – pair of thick wool socks.
(Subsequently sliding said sock into a stylish pair of leather boots comes a close second.)
Falls can be crisp and winters can be cold as shit, so stock up on warm socks in the fall and get ready to wear them for the next four to six months.
Socks are one part of a man’s wardrobe where you can throw caution to the wind have some fun, without worrying that your look is too “out there.” Stock up on the core fall colors, sure, but don’t be afraid to grab some bright colors and fun patterns, too. Remember: style doesn’t have to be stuffy!
Where to Get Wool Socks:
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 other leather accessories.
And if you’re ordering online, you may want to consider sizing down.
A lot of gloves tend to run larger, and ideally you want them to fit snugly like the ones pictured here, not flap off your fingers.
Where to Get Men’s Leather Gloves:
Lighter Weight Scarf
Guys tend to shy away from scarves until the weather really requires them.
(And even then, there’s a misinformed cohort who refuses to wear them on the grounds that they’re “for girls.”)
That’s a damn shame, because when you learn how to 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.
Try paring a lighter scarf with a blazer or lighter weight jacket for a layered look that’s warm, put together and sharp.
Where to Get Men’s Scarves:
Lighter Weight Scarf
While metallic sunglasses like aviators look sharp as hell, the metal frames can get kind of cold come fall.
Plus, acetate (the material used in most non-metal sunglasses) frames tend to come in chunkier styles that look better with your substantial fall layers.
You can check out my post about some of the best men’s sunglass brands to find out where to get well made shades that are worth your money.
If you’re less concerned about the brand name and more interested in the shape and style of the frames, you might want to skip right to my post about the most classic men’s sunglass styles to see a few of the most stylish options available.
Where to Get Men’s Sunglasses:
The preferred headgear of the Peaky Blinders, Statham’s Lee Christmas character in The Expendables and a host of real life style icons ranging from Brad Pitt and Jon Hamm to Daniel Craig, Ryan Reynolds and countless others, the newsboy cap is a great way to look casual and cool (while, ironically, keeping your head warm).
Pair it with a leather jacket and/or a chunky sweater like Statham does here, and you’ll be able to go pretty much anywhere in style and comfort.
Where to Get Newsboy Caps:
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.
Where to Get Facial Hair:
- In my personal experience? Irish and Italian ancestors.
You’ve Nailed Men’s Fall Fashion
Now Take the Next Step Toward Sharper Style
Understanding the most essential men’s fall fashion pieces is a great first step toward looking awesome come autumn.
But just as autumn is only one season, knowing what to wear in the fall is only one small part of putting your best face forward.
To really look sharp and stand out, you have to know how to nail the details—all the details.
Fortunately, you don’t have to struggle to figure out which details are the most important to optimize.
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More Men’s Style Advice from Irreverent Gent:
- Thursday Boots Review
- The 8 Most Stylish Men’s Shirts Colors
- Public Rec Pants Review
- How to Dress Better for Guys
- How to Wear a Suit: A (Ridiculously Comprehensive) Guide to Suiting Up in Style
More Men’s Fall Fashion Advice from Around Ye Olde Interwebs:
Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a (patient, if long-suffering) Toronto sports fan and the husband of a wonderful (and fortunately much more patient) wife.