Fall is a wonderful season, but I’m not making any groundbreaking revelations with that claim.
But is it the changing leaves, crisp air, and kickoff into the holiday season that makes us so fond of autumn, or is it our inner monkey brains yearning for safety?
Think about it—fall is as predictable as it is gratifying. Pumpkin spice everything right on September first, stuffing your face with buffalo chicken dip as the Sunday Night Football anthem lulls you into a food coma, and not having to think at all about what you wear. Jeans, hoodies, jackets—whatever keeps you warm.
I would argue there’s no better time of year to suppress our simian tendencies and try something new.
Something so ridiculously stylish that it sends shockwaves through the apple orchard. Looks that will have every other guy giving you snake eyes as his internal dialogue mutters “Look at Mr. Hollywood over here treating the pumpkin patch like a runway…dammit he looks good.”
Perhaps you’re set on tees, trousers, and trainers, and you simply need a statement jacket? I’ve got you covered by category.
Things move quickly in fashion, but I’m not one to recommend swagger that isn’t shelf-stable. Here’s what my crystal ball predicts will be the biggest hits and where they are in your wardrobe.
Mid-Layers
Roll Neck Sweater
I’m selling trade secrets here, but seriously, get you a roll neck sweater. You’ll be the most dapper gent at the pumpkin carving soiree, and I can almost guarantee nobody will be cramping your style as we’ve got a ways to go before this wave crests.
I love roll neck sweaters because they incorporate the best part of every fall sweater and omit the bad ones. The elevated neckline is dressier than a crew neck, it’s less claustrophobic than a turtle neck, and most roll neck sweaters feature a heavy-gage weave that screams holiday festivity—without the goofy santa embroidery.
Noragi Jackets
As far as fall layers go, a Noragi jacket is an underrated gem. They’re one of the more casual pieces on this list, and while cardigans common midweight layer with an open-front silhouette, few menswear pieces offer such a unique approach to layering.
Akashi-Kama’s Noragi Jacket is the one that’s piqued my attention the most recently. The look just clicks with all of the Japanese workwear in my closet, and I’m a huge proponent of its made-in-USA quality.
This Noragi Jacket shouldn't be overlooked for any guy who values the art of layering. Versatile, stylish, and believe it or not—made in the USA.
Johnny Collar Sweaters
The Johnny collar sweater is a nod to vintage style, and like roll neck sweaters, are an under-utilized sweater design for dashing layers of warmth.
It’s perfect for those early fall days when the weather hasn’t fully committed to being cold. If you want to take the handsomeness a step further, something like SuitSupply’s Sand Ribbed Long Sleeve features a ribbed fabric and a structured placket.
With a cozy mix of wool and cashmere, there's simply no better time of year to sport something this suave. The slim fit and buttonless placket give it a sleek look, while the ribbed fabric delivers a cable-knit look without the volume of the real thing.
Outerwear
Modern Quilted Jackets
Quilted jackets are a fall staple, but I’ve never been drawn to the heritage aesthetic of hunting jackets. Like trench coats and fedoras, one wrong move and it begins to look like a costume. In this case, a British aristocrat hunting fowl with his troupe of hounds.
Swapping out longer cuts for a quilted jacket that falls just below the belt (or even a slight crop) is the easiest way to usher the quilted jacket into the 21st century. For something even sleeker, Tom Beckbe’s Logan Quilted Bomber nails this look. It’s an inventive mix for sure, but something about the stitched geometry looks so good with fabric cuffs and a fold-over collar.
Corduroy Blazers
Corduroy blazers have have a certain vintage, 1970s appeal, yet they remain timeless in their style.
In rich chocolate, a corduroy blazer is especially fitting for the season, and the texture combination opportunities are a playground for decadence. Blazer, matching pants, and a denim shirt underneath? Fuhgettaboutit.
Shearling Coats
Shearling coats have always been a head scratcher to me. They’re functionally warm, luxuriously cozy, with a stark contrast between milky fur and golden leather is candy for the eyes.
So why aren’t they more popular? I think most guys feel they must fall under a certain archetype—the Tom Hardy or Paul Newman type—to pull them off.
Shearling jackets are paradoxical like that. Once both arms are through, your confidence rises to the level that former you thought was a prerequisite to rocking one. False. Fall 2024 is the year to let the fur fly.
Footwear
Engineer Boots
If there’s one piece of footwear that perfectly captures rugged sophistication with all of the durable substance to back it up, it’s the engineer boot.
Originally designed for—you guessed it—engineers and workers, this type of boot has an edgy personality to it akin to cowboy boots, but they’re much easier to incorporate into a fall outfit.
Pair it with the right jeans or chinos, and you’ll be stomping in style until the ground thaws.
Moccasin-Inspired Footwear
Clark’s Wallabies had a starring role in “Breaking Bad” thanks to Walter White, but don’t think the hype is over.
Moccasin-style shoes are still going strong, and for good reason. They have an easy-going vibe that’s hard to beat, and if you can score a nice pair made of high quality suede, they’ll see years of leaf-peeping expeditions to come.
Accessories
Printed Scarves
Fall wardrobes can get a bit drab with all those solids, which is why it’s essential to incorporate rich textures such as cable-knit wool sweaters and tenured denim.
Sometimes I’m still in need of some pizzazz, which is why I keep a printed scarf as a “break in case of emergency” resolution in my closet.
Drake’s has been at the forefront of this trend, turning what could be a simple accessory into a statement piece. Whether you’re draping it over a coat or knotting it under a blazer, a printed scarf is an easy way to inject some visual excitement into your look.
Statement Socks
If you’re the type who cloaks their socks under a long inseam in shame, that too can change with the season.
This doesn’t apply to your boot game, but with loafers, derbies, or German Army trainers, that subtle pop of color speaks to a man’s ability to dress himself with intention.
Having performed some deep e-comm recon, London Sock Company’s Shaken & Stirred 6-Pair Box is my #1 choice for fall undergarments. They’re made of Scottish Lisle Cotton, which sounds a whole lot fancier than “75% polyester, 20% acrylic, 5% spandex.” I’m willing to bet they feel just as nice as the patterns are cool.
This 6-pack of Shaken & Stirred socks puts a modern spin on traditional English Houndstooth featuring designs by award-winning Eleni Kyriacou. And if they weren't elegant enough, they're made of 74% Scottish Lisle cotton.
There’s no coincidence why fall is nicknamed “dressing season.”
It should be about embracing change and exploring new combinations. Whether it’s mixing patterns, trying different color palettes, or adding a new type of outerwear to your rotation, the options are endless.
This autumn, show the world you can sport anything—even if it’s just for that extra nod of approval at the tailgate. I won’t judge.
