Let’s face it: The past decade in men’s style has been a roller coaster ride filled with unexpected surprises. And in the era of fast fashion, hypebeast fashion culture, and blink-and-you-miss-it fads, it can be hard to come up with a reliable wardrobe that won’t leave you feeling outdated by the end of next season.
Luckily, we’ve consulted some of the best stylists and fashion experts in the industry to fill us in on the men’s style trends that you should actually try in 2020 that will have you looking your best all the way through the year—and beyond. And if you’re looking for more ways to upgrade your look, check out The 20 Best Winter Coats for Men.
Best Life's editors have scoured the internet to bring you the best products out there, and we're hoping you'll love them as much as we do. Full disclosure: we may earn a commission for anything you purchase through links on this page, but that doesn't mean you'll pay more for them (we'd never do that to you!). Pricing and availability are accurate as of the piece's initial publication date, but it's the internet and we can't guarantee that these sweet, sweet deals will last forever, so scoop them up before someone else does!
1 | Vintage baseball caps
Ebbets Field FlannelsThrowing on a baseball cap used to be the kind of fashion move used to cover up a messy hairdo in a pinch or to hide in plain sight from paparazzi. But according to some style experts, they’re actually a casual, effortless way to elevate your look this year.
“A good cap can take a basic outfit to the next level,” says Nicholas Bailey, stylist and founder of NICKSAYSGO.COM. “These vintage caps from Ebbets Field Flannels are 100 percent wool and 100 percent timeless. Personally, I prefer their wool caps because they dress up just a tad bit better.” And if you’re looking for ways to make your home look as good as your new outfit, check out these 15 Easy Home Upgrades That Will Make Over Any Space in 2020.
2 | Nike Air Force Ones
NikeMake no doubt about it: Footwear can absolutely make or break any outfit. But that doesn't mean boring brown and black leather shoes are your only option if you want to look put together.
“Nike Air Force Ones are the definition of being both trendy and classic at the same time,” Bailey says. “They’re best sellers for a reason and go with absolutely anything you can think of.” He feels that the versatility of the style is also a huge plus. “If you don’t own the all-white version, grab a pair. If you [already] do, explore and snag a pair with some flair.”
3 | Comfy beanies
J. Crew
While rocking a perfectly coiffed hairdo will always be in style, on those days you just can't bother to blow dry, a stylish beanie will serve you well.
“A perfectly cuffed beanie is one of my most highly recommended essentials: They’re trendy, but also timeless,” says Bailey. “Cashmere, wool, or anything that feels right to you—it’s your choice. Just get one!” And if you’re looking for more ways to get through the colder months, check out these 10 Must-Have Technical Jackets for Men and Women.
4 | Updated joggers
Daily PaperOne of the most pervasive style themes of the past decade has been taking casual elements of fashion and making them look as chic as possible.
“Joggers are another trend that have stood the test of time,” says Bailey, “but if you really want to stand out, look for a pair with taped sides like these ones from Daily Paper.” This simple element adds a pop to the shaped fit of the pants, making them more unique and eye-catching.
5 | Knit sneakers
GreatsLooking for a wearable accessory that can instantly dress up or dress down any outfit? Try a knit sneaker.
“Everyone needs a sneaker that can take them from the office to happy hour and then on to date night,” says Bailey. For him, the trendiness of knit sneakers is only made better by their functionality and how easy they are to care for—and he says the Greats Royale Knit sneaker is a particularly solid investment. "They’re breathable, machine washable, and pretty much go with anything possible." And if you’re looking for something sturdier to get you through blizzard season, check out these 20 Pairs of Men's Winter Boots That Go With Everything.
6 | Graphic tees
End Clothing
Tapping into some of 2020's biggest trends doesn’t have to mean investing in expensive new suits or pricey statement pieces that might look outdated by next winter.
“No matter your style, don’t be afraid of a solid graphic tee to throw in the rotation,” says Bailey. “They can be simple, flashy, or anywhere in-between. Pair them with denim and sneakers or chinos and an overcoat. Endless possibilities!”
7 | Relaxed fit pants
Need SupplySkinny jeans and slim-cut pants may have dominated style trends for the past ten years, but according to experts, 2020 has something completely different in store.
“After being in hiding for over a decade, relaxed-fit pants are slowly creeping back into the forefront of style,” says Bailey. “Brands are recognizing that and they’re delivering some solid styles." Looking for a good place to start? He recommends these tech pants from Need Supply as a starter piece.
8 | Statement rings
MiansaiLet’s face it: When it comes to accessorizing, it can be hard for lots of guys to find pieces that actually work with their look. But according to style experts, 2020’s trends are all about embracing statement pieces like bold jewelry. “It can be hard to find the perfect accessory, but rings are never a bad choice,” says Bailey. “Miansai has plenty of great options at great prices, including this unique Cigar Band ring.”
9 | Minimalist wallets
PaperwalletLike it or not, the look and functionality of your billfold factors into your look. Style experts say that for 2020, thin is in—at least when it comes to your wallet.
“Minimalist wallets have been booming in popularity over the last few years, but it's still routine to see men and women lugging around hefty leather wallets packed to the max with things they don't need,” says Elad Burko, the founder and CEO of Paperwallet. Luckily, paring down your wallet with a slimmer billfold like this one does more than give you incentive to ditch those old receipts—it can also help streamline your look when you're wearing a slim-cut suit or jeans.
10 | Streamlined messenger bags
Nordstrom RackFor decades, men’s style trends dictated that the only options available for carrying belongings were briefcases, pockets, or backpacks. Luckily for everyone, 2020 has more in store for stylish guys.
“Hands-free daily commuting isn't just a necessity for women,” says Jaime Diehl, stylist and founder of Jaime Diehl Style. “Guys, there's a crossbody or messenger bag for you, whether your personal style is more refined and classic or you like urban street style." This leather messenger bag from Nordstrom Rack is the perfect bag for 2020, and will look just as good with your preferred office wear as it will with your favorite t-shirts and jeans on the weekend.
11 | Tropical prints
Bonobos“Whether your personal style is bold, high street, or classic there's a tropical shirt for you. If you prefer to live the island life in subtly — think suburban neighborhood pool party — your best bet is a muted neutral print that you can pair back to navy or tan shorts," explains Diehl.
“For 2020, I'm excited that Bonobos is a one-stop shop if you have a personal taste for both bold options and classic. They also have great prints for the big and tall guys."
12 | Gray hair
Unite HairWe’ve come a long way since the days of covering your salt and pepper to stay fashionable. Today, the Silver Fox look is hotter than ever.
“Everyone loves this look and 2020 is the year to try it if you haven't already,” says Savannah Fincher, hairstylist and corporate educator for Blo Blow Dry Bar. So how do you embrace your inner Anderson Cooper? “Take your strands from grey to silver and maintain the tone by washing weekly with a purple shampoo. My personal favorite is Blonda by Unite," she says.
13 | Runner shoes
AdidasIt’s not often the case that style meets function when it comes to fashion trends. But in 2020, one of the hottest looks involves the growing popularity of chic shoes that also happen to be great for actual physical activity.
“The popularity of runners shot to the moon in 2019 and they haven’t slowed down,” says Bailey, who recommends the Adidas Ozweego. "Not only are they well-priced, but they’re also just the right amount of sporty without going overboard.”
14 | Sustainable fashion
Gaucho Buenos AiresFast fashion may have reigned supreme for the past decade, but growing awareness about its harmful impact on the environment is beginning to shape the trends we’re seeing in 2020.
“In today’s market, fashion is no longer just a product, price point, or trend. It’s more about the entire brand experience and how you make people feel,” says Lautaro Amadeo Tambutto, creative director of emerging luxury sportswear and leather accessories brand Gaucho – Buenos Aires. "We expect to see smaller production with less waste [and] more upcycled and renewable materials," like this sweatshirt inspired by the artisan weaves on gaucho blankets.
15 | Woodsy fragrances
DiptyqueIn 2020, it's time to dazzle people with a woodsy scent that’s as captivating as your look.
“Diptyque makes some of my favorite fragrances out there,” says Bailey. “With Tam Dao, you’re looking at the perfect blend of sandalwood, cedar, and cypress—a blend that’s really made to impress.”
16 | Western-style accessories
AriatIt's not just Lil Nas X bringing country western wear into the mainstream.
“Western style is showing up all over the runways and red carpets alike,” says Shane Holman, Senior Director of Global Western Trend and Market Development at Ariat. “It is a great time to lean into the iconic and truly Americana shoe style—the cowboy boot.” The surprising versatile footwear style can be tailor-fitted to work with practically any outfit and makes for a comfortable-yet-rugged option for anyone on the go. But why stop there? Other cowboy-style accents like bolo ties and brimmed hats are just as fashionable this year.
17 | Trunks as undergarments
AmazonAs it turns out, one of 2020’s biggest accessories is one that few people will see.
“Trunks are the next step" in the fashion world, says Jack Epsimos, Brand Owner of KRONIS Trunks. “They’re the middle ground—the goldilocks zone, if you will—and the perfect way to combine support and comfort." Besides: You can’t look fantastic if you don’t feel comfortable! And if you’re looking to get a head start on updating your underwear game, use the discount code 20BestLifeat check out to get 20 percent off your first purchase of these trunks on Amazon!
