There’s a lot more to men’s fall fashion than throwing on a shacket and some dark denim, though that’s certainly a good start. For a proper fall fashion reset, you’ll want to consider your entire wardrobe — all the way down to your socks. But don’t be intimidated.
We spoke to men’s style experts to come up with a comprehensive guide to what stylist and founder of Pivot Image Consulting Patrick Kenger calls “menswear’s favorite season.”
The key to men’s fall fashion? Layers and versatility.
“Fall gives you the opportunity to style more outfits by simply layering different pieces together,” says men’s stylist and content creator Najm Loyd. “This is the season to experiment with new outfits and color combinations and [to] stay cozy while doing so.” Kenger also thinks of fall as an opportunity, describing it as the “Goldilocks season of clothing.”
“We can start layering and have a lot of options when it comes to the items and fabrics we can wear, more than any other season,” Kenger says.
Building a balanced wardrobe is important too, which brings us to our second point: versatility. Dan Gilligan, vice president of men’s design at Abercrombie & Fitch, calls this the “key to a winning wardrobe.”
“From the endless summer of September to the temperature fluctuations right up to the holidays, you need a smart combination of pieces that can adapt,” he says. Jian DeLeon, the men’s fashion director at Nordstrom, agrees.
“A great transitional wardrobe is about having go-to versatile pieces that work with each other,” DeLeon says. “A shirt jacket can be worn over a knit sweater on temperate days, but also works underneath a topcoat for when the weather becomes more brisk”
More than anything, streamlining your wardrobe is the chance to showcase your individual style and feel proud of how you’re presenting yourself each and every day. “When I think of fall fashion, I get excited about new beginnings and the opportunity to express a new outlook,” says Ian Velardi, VP of product design at Bombas. “You don’t need to have a new wardrobe to make your look feel fresh — you can change up the way you’ve been wearing something the past few years.”
Ahead, we’ve consulted expert stylists, our in-the-know editors and everyday, fashion-loving guys to come up with a list of pieces and brands that embody these principles so you can start fall prepared to show off your new look.
J.Crew is an undeniably great place to shop year-round. The brand’s timeless and effortless styles are functional and high quality, and the breadth of options makes it a fun destination for spicing up your most essential pieces. When it comes to sweaters, there’s something about having a wide range of styles, colors, materials and designs to choose from that makes curating your fall wardrobe a little more fun.
You can’t go wrong with this versatile everyday crewneck sweater, which is available in sizes XS through XXL.
Snag the navy shade of this half-zip style and you’ll have a classic fall piece that will pair with most outfits.
If you’re looking for a warm, substantial sweater to take the place of outerwear this fall, this cashmere cable knit is a timeless choice.
“If you’re a fan of J.Crew, you’ll love Alex Mill,” says New York City-based fashion stylist and editor Audree Kate López. That’s because the brand was founded by the son of a former J.Crew CEO as well as past J.Crew and Madewell designer Somsack Sikhounmuong. And like those brands, Alex Mill kills it when it comes to basics like sweaters.
López recommends this cozy, relaxed cotton fleece sweatshirt, which comes in four colors inspired by vintage pieces.
Weighty, extra-soft and easy to pair with any outfit, this washed cashmere sweater would make an excellent addition to any fall wardrobe.
Since this knit is as breathable as it is warm, you can wear it when it’s blustery or toasty.
Whether it’s a fashion-forward cashmere crewneck or a lightweight cardigan, Banana Republic has your sweater needs covered. The timeless brand is a great retailer for year-round fashion, though its range of options and overall quality-to-price ratio make it an easy one-stop shop for all your wardrobe needs, from basics to statement pieces, outerwear, accessories and, of course, sweaters.
Want cashmere at non-cashmere prices? Try Banana Republic, Kenger says. “The quality at BR has felt higher recently, and their stores have undergone some great renovations.”
When it comes to fall staples, shackets are must-haves. But sweater polos (swolos?) deserve a shout-out too. This one takes inspiration from the past with its colorblocked retro pattern and is made from extra-soft mercerized cotton.
Elegant, comfy and perfect for sitting by the fire with a cup of tea, this stylish half-zip is great for a casual weekend ‘fit.
Beloved by outdoorsy and active guys since 2010, Huckberry specializes in high-quality clothing, gear and accessories that work equally well for everyday life and the outdoors. The brand’s design manager, Nick Kemp, says that when it comes to sweaters, you should be looking for pieces you “can layer and wear stand-alone” and that “fit in seamlessly to your wardrobe.”
Kemp calls this the perfect sweater for early fall. “Not too heavy and not too light,” he says. “It’s great as a jacket substitute for those nights when it’s just a little too chilly but not cold enough for a jacket.”
For over 100 years, Barbour has designed some of the most luxurious, buy-it-for-life menswear on the market. This incredibly well-made marbled lambswool and cotton half-zip is proof of that.
While this may look like your standard cardigan, it’s actually made from an itch-free combination of recycled cotton, acrylic and polyester. The material is soft, flattering and super comfortable.
When it comes to fall, versatile pieces are key. And that’s exactly what AYR specializes in. “You want to find something that’s going to get along with everything else you already own, that’s going to fit right into your day-to-day,” says Brice Pattison, VP of menswear at AYR. “High-quality, well-made, well-fitting things that you don’t have to overthink.” At AYR, that manifests in the “all year round” — hence the brand’s name — approach to dressing.
Though not quite a sweater, Pattison describes this piece as “versatile and as good a layer as any sweater.” It’s incredibly lightweight, machine-washable and made from 100% merino wool, which is three times more moisture-wicking than cotton, naturally wrinkle-resistant and antimicrobial. “Layer it over tees and under sweaters without getting overheated,” he says, “or wear it on its own. The quality of the wool’s so high it’ll never feel scratchy.”
Since fall is about layering, we can’t publish this guide without including a sweater vest. And AYR’s The Grad is one of the best. It’s sophisticated, subtle and made from extra-fine merino wool.
Over $200 is a lot to spend on this sweater. But what if we told you it was so well fitting and versatile that you could pair it with anything? That, combined with the fact that it’s made from Italian merino wool, should be enough to sell you.
Designer Todd Snyder’s eponymous brand, inspired by his love for New York City, is a go-to fall fashion destination for many of our experts. Specializing in well-tailored, beautifully designed and expertly crafted pieces across the board, the brand’s quality and attention to detail is particularly standout when it comes to one of our most often-worn pieces: sweaters.
Cardigans are a foolproof layering piece. Throw this luxe cashmere option over any of your go-to tees to stay warm and look super polished.
Kenger recommends this bestseller from the brand. The sweater’s fabric is a bit lighter than cashmere but just as comfortable and soft.
All the comfort of a sweatshirt, all the style of a tailored sweater. And it’s available in colors perfect for fall, including Bisque, Original Navy, Army Green and Antique Grey Mix.
López says that workwear brands like Carhartt, Wrangler and Dickies are gaining popularity, making their way into street-style outfits. Not only are pieces from these brands on-trend but they tend to be rugged, affordable and accommodating for men of all body types. That’s certainly true of Dickies pants, which offer some of the best value — and widest range of sizes — that you’ll find on our list.
If there’s one piece that put Dickies on the map, it’s the brand’s 874 work pants, which come in a huge array of colors and sizes. “They’re cooler than a chino, can be dressed up for a night out or styled casually for a weekend look,” López says.
Though they’re limited to three colors (for now), Dickies regular fit cords are another fall favorite. And like most pants from the workwear brand, you can mix and match the inseam and waist sizes.
Still clinging to your skinny jeans from 2010? Get out of your comfort zone and try something new with these heavyweight relaxed fit carpenter jeans, which are a steal.
If you’re in search of new pants that work equally well in a business-casual office and for apple-picking dates, Bonobos truly nails the sweet spot of polished yet still stylish. A favorite of our director of business development, Hunter Capobianco, the brand offers a range of incredible, high-quality pieces across the board, but we’re partial to some of its pant styles, which are comfortable, durable and, like many great fall staples, easy to incorporate into your wardrobe, no matter the season.
“These are my go-to pants throughout the year,” says Capobianco, who admits that he loves them for the fall as much as he does for every other season. “They are comfortable, look great and go with just about anything.
These selvedge jeans, made from a high-end Japanese fabric, feature just enough stretch for ultimate comfort without sacrificing style.
“Uniqlo is pretty much my go-to for anything,” says associate testing writer Joe Bloss. The Japanese casual wear brand has skyrocketed to global popularity with its affordable prices, durable construction and range of versatile pieces, which makes it no surprise that the brand comes recommended by various guys.
“I love corduroy pants in the fall and winter,” says LA-based menswear content creator Vince Lee. “They add a bit of richness to any outfit.”
We’re big fans of the return of cargo pants — comfortable, practical and effortless. What’s not to love?
We can’t get over the price of these selvedge jeans, which were co-produced with Japanese denim legends Kaihara. Wear them for years and you’re guaranteed a sick fade.
There’s nothing like a great pair of jeans to tie together an outfit, and there’s no brand that nails denim quite like Levi’s. The classic American brand has been a go-to for decades when it comes to all jean styles, and today it carries a comprehensive range of styles, sizes, fits and more. In short, if you’re in need of some new jeans for the fall, you can’t go wrong with Levi’s.
“There’s nothing quite like a pair of Levi’s 501s,” says Velardi, who wears his nearly everyday. “They’re part of my daily uniform.”
“These are giving old-money style, which is super popular right now,” Lee says. He calls the slouchy style a “classic, all-year-round denim” option.
“These relaxed jeans are such a classic staple for fall,” Lee says. They’re perfect for throwing on over chunkier boots for that effortless yet polished look.
The popular direct-to-consumer brand is one of our favorite places to stock up on staples without breaking the bank. By skipping the retailer and, in turn, the traditional retailer markup, Everlane is able to work with ethical factories, focus on quality materials and keep prices down. And it shows in its collection of pieces, which include stellar pant options and an impressive range of denim.
“Pleats are no longer your father’s or grandfather’s trousers,” says New York-based celebrity stylist Michael Fisher, whose clients include Sebastian Stan, Adam Driver, Michael Shannon, Kieran Culkin and Lee Pace. “This trend isn’t going anywhere,” he adds. “[It’s] back and cooler than before.”
A pair of well-fitting dark-wash jeans are the perfect transitional piece. They’re versatile, sleek and easy to dress up or down.
Whether you’re running errands, traveling or just looking for a pair of super-comfortable pants, this pull-on waistband option is sure to be a casual day go-to. The shade Beech just screams fall.
Abercrombie & Fitch
“Fall is synonymous with layers,” Gilligan says. “I personally love the cooler weather and the chance to get out the sweaters and jackets again. Layers provide an opportunity to introduce texture and dimension to outfits that maybe wouldn’t exist as much during warmer weather.” And when it comes to perfect-for-layering jackets in a range of styles, Abercrombie & Fitch boasts a super-impressive collection.
OK, so it’s not quite a jacket, but seeing as we don’t have a vest section, we’ve got to include this military-style utility vest in our head-to-toe guide. It’s a perfect piece for layering, especially when paired with a flannel shirt.
“You can’t go wrong with a black bomber jacket,” Gilligan says. “This one is made with super-soft faux suede, and the ottoman rib cuffs give a nod to varsity jackets.”
Abercrombie & Fitch has come a long way, replacing its brand-heavy, preppy clothes with more on-trend pieces like this cropped workwear jacket.
Outdoor apparel brand Kühl is the place to go if you’re looking for a practical jacket for the fall that is as high performance as it is stylish. One of the few privately owned and independent companies in the outdoor space, Kühl prioritizes the quality of its products and customer satisfaction over everything else, which has led to the performance-focused brand having a dedicated fan base.
This rugged trucker jacket is made from a super-durable, wind- and water-resistant wax-coated cotton canvas that softens over time and looks even better with wear.
“I bought this coat last fall, and it’s my favorite jacket for cool weather,” Capobianco says. “It’s light [and] water-resistant and looks sharp.”
This waterproof jacket is breathable, comfortable and super lightweight — perfect for packing up ahead of any unpredictable weather.
“We typically associate fall attire with outdoorsy types of items,” Kenger says, adding that, in general, the fabrics you’re looking for “should start getting a bit heavier and focus on being more robust.” Buck Mason, a brand that he recommends, is all about curating a collection of the very best basics in line with their commitment to craftsmanship and consistent high quality.
Kenger recommends this relaxed wool jacket, which has that outdoor, rugged and worn aesthetic he looks for in fall clothing.
This lightweight cotton twill jacket is the perfect polished layering piece.
If you’re looking to invest in a high-quality leather jacket that will last you years (and likely only look better over time), we can’t recommend this bestselling option enough.
Velardi calls a “navy wool topcoat the undisputed champ” of fall fashion. “There are lots of fit and style choices in this category, but it’s all about determining what works best for you personally,” he says. If you’re looking to invest in an option that will last you far longer than a single fall season, you can’t go wrong with Ralph Lauren, a brand that continues to create beautifully designed, well-constructed pieces beyond just polo shirts. We’ve selected pieces from the brand’s “blue label,” Polo Ralph Lauren, which strikes a balance between opulence and affordability.
This is Velardi’s top choice for a navy wool topcoat, and he recommends making sure to give yourself “enough room to comfortably layer under” and seeing a tailor to make sure your sleeve length is just right.
“What a great classic coat from Ralph Lauren,” says Lee, who loves that it’s a classic, minimal style that you can dress up or down.
This classic coat cut features a water-repellent taffeta and eye-catching accents like leather trim and a corduroy collar.
“There’s nothing like a new great outerwear piece,” says Fischer, who recommends adding a statement coat to your fall rotation. “This season, there are many oversized options to accommodate all the layers comfortably.” Tim Washington, an New York City-based music marketing manager, agrees, recommending the Swedish brand Weekday, which offers a ton of fashion-forward styles at an accessible price point.
An oversized wool coat always looks cool. This substantial option — which is lined and boasts multiple pockets — is perfect to take you right from fall into winter.
While it’s a jacket and not a coat, this classic puffer option is a great transitional outerwear option. We’re big fans of the mock neck and elastic hemline and cuffs.
“Everyone needs a good top coat,” Kenger says, “and Suit Supply has a lot of options with fabric from great mills.” The Dutch brand, which specializes in custom suits and menswear, is quickly rising in global popularity, in large part due to its Custom Made program that boasts personalized online advice, tools to help you customize your fit and expert in-store alterations.
Kenger recommends this light-gray Vicenza overcoat, an elegant outerwear option that’ll keep you warm even as the months get colder.
If the autumn weather in your area includes unpredictable weather or rain, trench coats like this one — made from water-repellent cotton — can be a stylish way to keep dry.
This classic, beautifully tailored raincoat is perfect for throwing on over any outfit to stay dry during fall showers.
A favorite among many of our experts, New York City-based brand Thursday was founded out of a frustration that founders Nolan Walsh and Connor Wilson had while shopping for their own boots in 2014. There weren’t a lot of stylish yet durable, unique yet practical options available at an accessible price point. Today, the brand is a staple for men across the world who love its range of fashionable styles that are equally comfortable and well constructed.
Kenger recommends this classic, sophisticated style from the brand. “Great boots without a ton of markup,” he says.
You get “such great quality and comfortable boots” from Thursday, says Lee, who’s a fan of this durable, slightly more rugged option.
It’s hard to find a boot that’s as versatile as this one. Dress it up, dress it down — they’ll complement just about any fall outfit.
“Nothing beats a pair of Red Wings,” says our senior travel and money editor Andrew Kunesh. The iconic brand is well known for its protective work boots, which are designed to keep feet safe. Its heritage styles boast similar durability but are a bit more comfortable and conducive to everyday wear. Regardless of the style you choose, there’s no doubt that they’ll hold up well over time and against the elements.
If you only buy one boot for the rest of your life, it’s hard not to recommend these. Incredibly durable, comfortable and stylish, they’ll last you forever.
“I bought a pair of these in 2019, and they’ve withstood multiple New York City winters without skipping a beat,” Kunesh says. “Just make sure to maintain them with regular polishing.”
This super-versatile style is perfect for just about any and every fall outfit.
“Blundstone boots are perfect for fall transitioning into those winter snowing months,” Fisher says. The Australian footwear brand is well known for its easy-to-slide-on, unbelievably comfortable shoes, which are now available in an impressive range of material and style options. No matter what your fall looks like — whether it’s stomping through puddles, piles of leaves or just the streets of a big city — you can’t go wrong with a pair of Blundstones.
Add a little contrast to your ‘fit with these eye-catching Chelsea boots. The boots come in four colors, but the Stout Brown and Olive colorway is perfect for fall.
You can also opt for classics like all-matte black, brown or olive colors, Fisher says. This option boasts Thinsulate technology, which keeps your feet warm, dry and comfortable, no matter the weather.
Prefer a vegan boot? Not a problem. Classic Blundstone styles like this one are also available in fully vegan materials.
When it comes to Velardi’s fall shoe of choice, he opts for a classic: Clarks Wallabees. But whether it’s that iconic style, the brand’s desert boots or one of its newer styles or collaborations, Clarks’ ongoing dedication to comfort and durability has made it one of the must-have brands for fall footwear.
“The gum sole is crazy comfortable, and they look great with almost any pants,” Velardi says. “You can dress ’em up or just keep it casual.”
This everyday boot features the brand’s signature uber-comfy footbed. Plus, it’s completely waterproof.
We’re obsessed with the brand’s iconic desert boot, which is now available in nine colors, giving you plenty of options for fall.
Since the 1970s and ’80s when Dr. Martens were staples of the punk and new wave scenes, the UK-based footwear company has been a perennial favorite among the youth. Fans’ zeal for the brand’s iconic chunky soles and yellow stitching continues today, especially among men who’ve embraced the workwear trend. With their rugged designs — perfect for trudging through the mud — they’re an excellent choice for the fall.
CNN Underscored associate writer Maxwell Shukuya says he’s been wearing Dr. Martens Crazy Horse leather shoes for nearly a decade — a testament to their enduring appeal. “I love the contrast between the deep brown and bright yellow and that you can dress them up or down,” Shukuya says, though he prefers the oxfords.
Dr. Martens usually last a long time. But if you’re looking for a buy-it-for-life pair, spend a little extra on the Made In England series. Dr. Martens still produces these boots in their original English factory and uses Goodyear-welted lines.
The smooth leather 1460s have been one of the brand’s most popular boots since its debut in 1960. Get them in a classic Black or White, or go for a funkier color like Cherry Red, Green or Muted Purple.
“Fall is such a great time to mess around with different shoes — chukkas, loafers or sneakers,” Velardi says. And what is a must-have when you’re experimenting with different shoes? Different socks, of course! Bombas is a long-time CNN Underscored staff favorite and also where many of our experts go to when they’re looking for comfortable socks, especially warm ones that will pair well with boots throughout the chillier months.
“If you could only own one pair of socks, this is it,” Velardi says. “These socks were engineered to work with everything and anything … You get a refined-looking rib construction paired with the comfort of an active sock.”
Velardi describes these socks as ideal for any level of performance. “You get cushion and support in all the right places, and the yarn is the perfect combination of technical and natural feeling,” he says.
For no-show socks that actually stay on, snag this four-pack of Bombas. Even if you wear sneakers, they’re cut low enough that you won’t be able to see them.
Sometimes refreshing the pieces that aren’t necessarily on display but are crucial to your comfort is an easy way to start building a wardrobe you’re proud of. And what better place to start than with socks? “Gold Toe socks are my favorites,” Lee says. “They’re great quality and comfortable any time of the year.”
Perfect for your favorite fashion sneakers, these invisible socks are just what you need for those days where socks aren’t a part of the ‘fit.
Nothing screams fall quite like argyle socks. Gold Toe offers nine different color variations in its three-pack.
A fan fave, these classic crew socks boast a 4.5-star rating from over 18,000 reviewers.
“London Sock Company is my go-to for dress socks,” Fisher says. “Socks are a great way to show you have style, game and character.” He adds that he’s a big fan of the brand’s variety of colors and styles. The options are endless, and each is a perfect way to add that bit of elegant detail to any outfit.
Fisher’s collaboration with the brand is based on color theory and features six bold colorblock combos that are sure to catch people’s attention for all the right reasons.
The rich colors and fun dots on these socks add a bit of playfulness to any formal outfit.
Regardless of the season, this set of six will serve you well. That said, the red and yellow are perfect for the fall.
When it comes to a one-stop shop for all your fall accessories, Loyd recommends Madewell. From men’s wallets to sunglasses and belts, the brand carries a ton of styles and variety — all perfect for sprucing up your seasonal wardrobe. But that’s not all the apparel brand does. It’s worth noting their incredible denim selection, which is one of the best on the market.
“There will still be sunny days during the fall,” Loyd says. “These sunglasses really complete an outfit.”
“Madewell beanies should be in every man’s arsenal,” Washington says. This one is made with recycled cotton and polyester.
Elevate your fall ‘fit with this practical canvas tote, which you can carry with an integrated shoulder strap.
There are an endless number of watch brands to choose from. So when we come across one that’s truly unique, we can’t resist sharing. London-based brand Mr Jones Watches specializes in conversation-starting pieces that people can’t resist complimenting. Whether they make you think or just make you smile, the designs — many of which are created in partnership with artists — are the perfect accessory to any outfit.
Hand painted by designer and printmaker Fanny Shorter, this 20-jewel automatic mechanical watch features a lush jungle scene with the time hidden in the moon and the tiger’s stripes.
If you’re into the idea of a watch that’s also like an ever-changing work of art, this option features three colored discs to show you the hours, minutes and seconds as they pass by.
Powered by Swiss-made automatic mechanical movement, this unique watch was designed by Kristof Devos as a “gentle reminder to take it easy and spend time enjoying the moment.”
When you’re not sure exactly what you’re looking for — whether that’s a length of scarf or a type of cool-weather hat — it can be useful to browse a retail site like Bloomingdale’s, which Bruno recommends. Not only will they carry a range of product styles and types but you can discover different brands and better learn what types of products you gravitate toward. You might also find discounted products from some of your favorite high-end brands.
Belts are a year-round essential, but you’ll want to be sure you have enough color options to keep up with your different outfits. A perfect-for-fall tan shade like this option is a must-have when wearing similar colored boots or dress shoes.
Useful transitional pieces to have on hand, scarves are a great way to accessorize an otherwise simple outfit and keep you warm without having to add more layers.
For those sunnier days, switch out your summery baseball cap for a more muted color that’ll match with your jackets and sweaters all fall long.
While heading back into the office isn’t exactly back-to-school season, the fall might be a great time to refresh your office attire. “If you’re looking for a tie or a pocket square, my go-to is Tie Bar,” Lee says. “They have a great selection at great prices.”
If you’re going for that stylish academic look, this hunter-green tartan tie is perfect for pairing with a navy suit.
Pocket squares are an easy way to add a splash of color to any neutral suit, especially in this Burgundy color, which is fall embodied in a single shade.
With burgundy flowers and a reversible herringbone design, this versatile bow tie’s color palette is perfect for any autumn weddings or special events.
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