As we transition into fall, it’s not just the weather that’s shifting—our wardrobes are, too. Autumn presents the perfect opportunity to refresh your closet by bringing out those jackets and sweaters that may have been tucked away for months, or by hitting the online stores and adding in some stylish new pieces.
I like to call my styling clients “kings” because, with a bit of fashion guidance, they can truly feel like royalty. Whether it’s an investment in a classic pair of chino pants or a sophisticated sweater polo, there are several key items that every man should consider incorporating into his fall wardrobe.
For this fall style guide, I worked with the Cool Material editors to explore a range of wardrobe essentials—catering to various budgets—that can enhance your style and comfort during the cooler months. Drawing from standout brands such as Todd Snyder, Percival, and Buck Mason, we scoured the web to curate a selection of Maddy G– and editor-approved items, including a range of versatile basics and statement pieces. We can ensure you’re well-prepared to embrace the season in style. —Maddy Gustini
Todd Snyder Premium Cashmere Montauk Polo
Kicking things off with a Maddy G favorite: Todd Snyder is a must-visit for sweater polos. An open-collar cashmere sweater polo from Todd Snyder is a timeless choice. —Maddy Gustini
Buy: $348
Tecovas The Earl Roper Boot
[PARTNER] If you're gearing up for fall, make sure to snag The Earl, the ultimate roper boot by Tecovas. As the fastest growing western brand, Tecovas is all about high-quality craftsmanship and unparalleled comfort. The Earl, their original best-seller, is crafted from luxurious goat leather that sports a vintage patina right from the get-go and only gets better with time. Tecovas' commitment to quality and inclusivity makes The Earl a must-have for any bold fall wardrobe.
Buy: $315
Zenni Surfwatch Sunglasses
[PARTNER] We’re not ready to give up on those bright summer days just yet. So as you’re gearing up for fall, embrace the sunshine with a pair of shades from Zenni Optical. Our pick is the Surfwatch frames from the Zenni x Chase Stokes collection. The tortoiseshell frames make for a stylish pair of sunglasses offering advanced protection and hand-crafted premium acetate. Plus, the durable construction means they’re ready for any adventure this autumn.
Buy: $50
Buck Mason Wornwell S/S Camp Shirt
Whether the temperature is dropping and you need a layer-able shirt, or the weather is still too warm to break out that sweater, you'll want a handsome short sleeve button down in your arsenal. Buck Mason is the king of menswear basics, and you can never go wrong with their classic camp-collar button-down. —M.G.
Buy: $138
G-SHOCK G-STEEL GM700G-9A
[PARTNER] A dynamic timepiece is the perfect accessory to upgrade your style game. Sure your outfit looks good right now, but with the right watch your fall ensemble will be complete. We’d recommend one of the latest releases from G-SHOCK: an impressive metal-covered watch that is sure to turn heads. The striking, textured timepiece includes a bevy of functions like world time, 5 daily alarms, super illuminator LED, and more. Complete your look this fall with the latest release from G-SHOCK, available in both gold and silver color options.
Buy: $240
LiveWire Mulholland Electric Motorcycle
[PARTNER] The only thing better than a motorcycle ride on the open road, is a motorcycle ride on the open road during peak fall. The crisp air and the beauty of leaves changing colors offers riders the perfect opportunity to take a break from the normal routine and embrace the great outdoors. There are few better options than LiveWire’s Mulholland motorcycle for a fall ride. Weighing 432 pounds, this electric beast rockets from 0 to 60 in 3.3 seconds with 84 horsepower and 194 ft-lbs of torque. Featuring a relaxed, upright rider position and Dunlop tires, it's built for both urban agility and open-road dominance so you can tackle those winding mountain roads in the height of autumn.
Buy: $15999
Asket The Overshirt
Fall is ideal for layering, with chilly mornings, warmer afternoons, and cool nights. An overshirt is the perfect solution, offering versatility for layering over tees, tanks, and sweaters. It’s a great addition to your wardrobe, seamlessly adapting to changing temperatures and enhancing your overall style. This particular example from Asket is simple, approachable, and stylish. —M.G.
Buy: $195
Arete Performance Quarter Zip Performance Jacket
[PARTNER] Born from the thrill for outdoor enthusiasts, the recently launched Quarter Zip Jacket from Arete Performance is the perfect garment for fall and winter outdoor pursuits. Arete was founded by dedicated explorer and adventurer Cliff Moss, who brings 35 years of extensive expertise in textile science, garment engineering, and clothing manufacturing. With Arete, Moss is blending adventure, comfort, and thoughtful design with each piece of clothing. The expertly designed Quarter Zip is a perfect distillation of Moss’ mission: made from 100% natural New Zealand merino wool, breathable, odor-resistant, and temperature-regulating and soon to be produced at Brooklyn’s Navy Yard. Arete’s aim is clear: to equip you for cold weather outdoor activities that keep your spirit moving. Arete prepares you for the journey ahead. Their heirloom-quality piece offers exceptional weight and craftsmanship that sets them apart from other well-known brands, ensuring you receive unparalleled value and a truly unique item crafted to last a lifetime.
Buy: $275
Percival Sardine Stripe Oversized Shirt
Lightweight and easy to wear but full of personality, Percival nails the return-to-office vibe for a summer that overstays its welcome. This subtly distinctive piece—yes, those are embroidered sardines—has a breezy fit and a vibe that says, that’s right, you did spend a long weekend in northern Portugal, but you had too nice of a time to post it on the grid. —Cooper Fleishman
Buy: $215
Levi's 505™ Regular Fit Selvedge Jeans
A pair of denim pants is a wardrobe essential. For the best fit, choose Levi’s, the undisputed king of denim. The Levi’s 505 Regular Fit offers unparalleled comfort and a classic silhouette that remains stylish year after year. Investing in these jeans ensures a timeless addition to your wardrobe season after season. —M.G.
Buy: $128
Nike Pegasus Trail 5 GORE-TEX
Make sure to prep for fall workouts with a rugged pair of running shoes. And with the winterized Nike Pegasus Trail 5, you can hit the trail in any weather. This beast sports a waterproof GORE-TEX upper and a 3-D print toe cap to keep your feet dry, while a rugged Nike Trail ATC outsole grips any terrain. The new ReactX foam midsole is 13% more responsive and eco-friendly, offering lightweight energy return and comfort. Reflective details enhance visibility, and a sturdy, high ankle cuff blocks debris. If you plan on tackling some trail running this autumn, scoop up the latest kicks from Nike.
Buy: $170
Buck Mason Parachute Poplin Ford Standard Carry-On Pant
When It comes to chinos, Buck Mason’s Parachute Poplin Pant is the gold standard. The straight leg fit is comfortable but not slouchy, and the straight leg fit looks good on so many different body types. If you are going to get one pair of pants this fall, make it this one. Another great way to jazz up a basic chino is to mix in different fabrics and materials—consider trying out this corduroy pair also from Buck Mason. —M.G.
Buy: $148
Astorflex Fastflex Suede Loafer
[PARTNER] The artisans at Astorflex have been handcrafting impeccable leather loafers for six generations and continue to produce some of the best footwear around. The Fastflex Suede edition is perfect for the changing seasons offering a cozy, buttery soft upper that will age beautifully over time. It’ll keep you warm and snug on cool evenings without overheating your feet on warmer days. If you are looking for a fashionable upgrade to your fall formalwear then snag a pair of these Italian suede loafers.
Buy: $168
Wax London Eldon Jacket Brown Suede
Suede, suede, and more suede, please! Suede was predicted to be one of the top trends men's fashion this fall, and I'm all about it! Wax London created a gorgeous brown suede jacket that is the perfect lifelong piece to have in your wardrobe. —M.G.
Buy: $520
Everlane The Cloud Crewneck Sweater
A crewneck sweater is really a must-have for everyone—in any season. But fall instantly brings sweater weather to mind! Enjoy a cozy coffee break in your Everlane Cloud crewneck or layer it over a button-down for a classic, timeless look. Embrace the season’s comfort and style with this essential piece. —M.G.
Buy: $67
Finisterre Shetland Fair Isle Jumper
I can already picture this sweater’s big debut. It’s the day before Thanksgiving in Vermont. I see board games on the table, whiskeys on the bar, pie in my stomach, and 100% Shetland wool—made in Scotland for the outdoorsy, B Corp–certified brand Finisterre—on my shoulders. Bring on the chill. —C.F.
Buy: $329
Oliver Cabell Low 1
If I could dream up the perfect white leather sneaker, It would be this one from Oliver Cabell. A classic white leather sneaker is a shoe that is enough versatile to be worn year round, not just in the fall. This beautiful shoe can even be dressed up with a suit pant and a blazer for more formal events. —M.G.
Buy: $199
Corridor New York New York Script Cap
A baseball cap adds a playful touch to any outfit. Whether you opt for a vibrant color or a classic New York design, it’s the perfect accessory to elevate a casual look and bring a bit of fun to a simple ensemble. —M.G.
Buy: $65
