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17 Style Essentials Every Man Needs for Fall, According to Stylists

Change your look as the leaves change color with these easy wardrobe upgrades you'll love.

Even though it may feel like shorts and sandals only worked their way back into your wardrobe rotation weeks ago, it's almost time to say goodbye to summer. But just because the seasons are changing doesn't mean you need to lose all hope for your look. So embrace that crisp feeling in the air and prepare to look your best with these men's fall fashion essentials stylists love.

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!

A denim jacket

young black man in denim jacket

Instead of trying some flash-in-the-pan trend, stick with something that's both in style and timeless when it comes to your outerwear this season.

"The Gap Icon Denim Jacket has its name for a reason," says Nicholas Bailey, stylist and founder of NICKSAYSGO.COM. "The non-stretch medium indigo denim is flawless and perfect for those cooler nights in the fall."

$80 at Gap
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A knit beanie

tan beanie hat
Bricks & Wood

Even though your hairstylist may finally be back in business again, it can sometimes be hard to sneak a touch-up haircut in as often as you'd like. This is where a stylish beanie can play a huge role.

"Knit beanies are truly a wardrobe staple," says Bailey. "They can take your outfit to the next level with minimal effort." Bailey says this one from Bricks & Wood is a particular favorite: "They're built to last, great for all seasons, and always make a statement."

$40 at Bricks & Wood
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brown suede loafers
Blackstock & Weber

It doesn't matter what you're wearing: If what you put on your feet doesn't look good, your outfit will fall flat. Level up your footwear rotation with some classic styles that are back on-trend.

"You'll never regret having a pair of quality loafers in your arsenal once fall hits," says Bailey. "My personal choice is the Ellis Penny Loafer from Blackstock & Weber. Beautiful acorn suede, Vibram sole, and natural tan calfskin? Buy now and thank me later."

$225 at Blackstock & Weber
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A lightweight crewneck sweater

tan crewneck sweater
J. Crew

One of the best parts about transitioning from summer into autumn weather is that layers become a style option again. And when it comes to adding a little something to your look, is there anything more versatile than a good crewneck?

"A solid sweater continues to be a mainstay of fall fashion," says Brittany Diego, celebrity stylist and founder of Fashion Mentor. "It's a transitional piece that will serve you all throughout the year, so it's worth it to invest in a good one."

$50 at J. Crew
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A graphic hoodie

black hoodie

Some people look forward to the return of autumn for the crisp weather and readily available pumpkin spice. Others are just excited to be able to wear their favorite piece of comfy clothing again.

"To spice up your wardrobe on those cooler days, swap out your solid hoodies for a graphic one, like those offered by Circulate," suggests Bailey. "Pair these up with your favorite sneakers and you're on your way."

$85 at Circulate
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Cargo trousers

white guy in gray cargo pants

According to style experts, fall 2020 style is all about borrowing a few looks from the past.

"Yes, the utilitarian look is back," says Diego. "Cargo pants are praised for being practical with more than enough pockets to hold your phone, keys, wallet, and other necessities while still being comfortable."

$140 at G-STAR RAW
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Crew socks

gray uniqlo socks

Take the arrival of a new season as an opportunity to spruce up your dresser drawers and give your feet a little flair.

If you're on the lookout for something that will stand out, try these handsome socks for a change of pace, "Uniqlo's crew socks come in over 40 colors," says Bailey. "With the perfect calf-length fit, these are a true staple for anyone's fall attire."

$4 at Uniqlo
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A check overcoat

white guy in checked overcoat
7 For All Mankind

Need an easy outfit topper? Fall is the perfect time to break out a stylish overcoat.

"Think of this as the classic trench coat's cooler cousin," says Diego, who calls it the "perfect finishing piece."

$695$519 at 7 For All Mankind
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A stylish face mask

blue face mask

Unless you were way ahead of trends, there's a good chance you didn't have a face mask in your wardrobe last fall. Keep yourself and others safe while looking great by picking a few of the fashionable PPE options out there.

"Get matching masks!" says stylist, art director, and model Michael Freeby. "Coordinated masks will keep you looking chic." This Mavi mask in particular is perfect for pairing with your favorite jeans for a dressed-down look.

$15 at Mavi
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A flannel shirt

young man in blue flannel plaid shirt

As the leaves begin to change color and the air becomes crisp, it's important to ask: Would it really be fall without a little flannel? Elevate your button-up rotation with the print that's as functional as it is fashionable.

"It's absolutely essential to have some cozy, fuzzy flannels thrown into the mix come fall," says celebrity stylist Eric Santiago. "Pick your favorite patterns and colors and you can wear them right through winter."

$72 at Everlane
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Casual suede sneakers

gray new balance sneakers
New Balance

When it comes to footwear, it's important to remember that style and comfort aren't mutually exclusive.

"A timeless pair of casual suede sneakers will take you a long way—especially in the fall," says Bailey. "The New Balance 993 is multifaceted and will treat you well for many fall seasons to come. They're classics for a reason."

$175 at New Balance
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A structured blazer

white guy in blue blazer
J. Crew Factory

If you're dressing up your look, it's hard to find a piece of clothing that gets the job done better than a well-fitted jacket.

Finding the perfect iteration of this look is all about proportions. In this case, "The shoulder pad sits just past the sleeve head, giving the jacket a crisp silhouette that complements the body's natural shape," explains Santiago.

$99 at J. Crew Factory
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A cross-body sling

white guy in gray shirt with black cross body bag

Let's be honest: You have too many devices and not enough pockets to carry them in—so opt for an accessory that will look good and make porting around your everyday items a breeze.

"As our required essentials have increased—and the likes of hand sanitizer and masks have become essential carry—small bags and slings are becoming indispensable," says stylist, trend expert, and designer James Jeffrey, who recommends this Bellroy Sling and its mini counterpart.

$99 at Bellroy
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A roll neck sweater

maroon turtleneck

Crewneck sweaters are as timeless as it gets. But you can also pull off a sophisticated look with minimal effort just by changing up the cut of your favorite fall top.

"Stock up on a few in neutral colors like black, navy, and grey, but if you want to experiment with color without committing to something too bold, this burgundy sweater will do the trick," says Diego.

$545$218 at Macy's
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A tie-dye shirt

blue and white tie-dye shirt
Holyland Civilians

When it comes to sprucing up your t-shirt drawer for fall, you might want to consider adding some tie-dye to your style arsenal. No, seriously.

Fashion stylist Michael Cook says he's "obsessed" with Israel-based Holyland Civilians' fall lineup."They ship worldwide and have really great unique pieces that will set you apart from the crowd, like this tie-dye from them that I love."

$62 at Holyland Civilians
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Sturdy leather boots

brown leather boots

To make a piece a true style essential, it has to be fashionable and practical. That's why stylists recommend getting your feet ready for the fall weather with a comfortable pair of sturdy leather boots.

"A great pair of leather boots, like these Florsheim Lodge Cap Toe Boots, will never go out of style," says fashion editor and stylist Corey Kelly, who notes the prevalence of leather in many designers' Fall 2020 runway collections. "Just picture it," he says. "You'll be on-trend, your feet will be comfortable, and (most importantly) you won't break the bank."

$125 at Florsheim
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Work pants

young black guy in blue cropped pants
Urban Outfitters

Remember: Just because you're dressing casually doesn't mean you have to sacrifice style. Traditional work pants can be a great way to make a statement while keeping things comfy.

"Dickies work pants have a naturally high waist and are super comfortable—they are work pants after all!" says Cook. "I would suggest a great pre-cropped style that ensures you have a fashionable edge."

$49 at Urban Outfitters
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Zachary Mack
Zach is a freelance writer specializing in beer, wine, food, spirits, and travel. He is based in Manhattan. Read more
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