When the weather drops and the air is crisp, nothing finishes off a fit for fall quite like the best jackets. (Ditto fall coats.) They not only insulate, but, more importantly, impart a sense of self. Take, for example, James Dean in Rebel Without Cause. The iconic cherry-red windbreaker he wore in the angst-fueled teen flick conveyed a lot about his character. He was an outsider, standing out amongst the sea of black, brown, and blue that his peers wore. He outwardly spoke—even cried—about yearning for acceptance, but his id and his impulses, as demonstrated by his eye-catching jacket, proved otherwise.
Yes, I am waxing philosophic in a round-up of the best fall jackets. I tend to do that sometimes, but, dear reader, no lies were told. The type of topper you wear lets people know the kind of guy you are—or might want to be—from the jump. It’s the first impression and, oftentimes, the lasting one. So, before you reach for any ol’ thing, make sure to pick the style that is right for you. Because, as you can imagine, the options abound.
From bombers in every conceivable fabric and anoraks in a spectrum of colors to field and motorcycle jackets with the same scope, you have the ability to tell your own story concisely with a single item. If you’re a rebel, take a page from Jimmy Dean and opt for a bright windbreaker. Are you artistically inclined? There are a slew of jackets with eye-catching prints or appliqués. But if you’re more laid-back dude, denim or a classic coach’s jacket will do nicely. To help narrow down your search, we corralled some choices—all of them great, all of them perfect for fall, and all of them telling.
Fluffy Yarn Fleece Full-Zip Jacket
If comfort is what you’re after, look no further than a fleece jacket. In the hands of Uniqlo, a purveyor of sleek fits, the style is as cozy as it is polished.
Unlined Eisenhower Jacket
The work jacket is a hard-wearing, no-frills style that just gets the job done, no matter what that job is. And after all these years, Dickies still makes a great option—and for less than fifty bucks, no less.
Trail Model Water Repellent Jacket
L.L.Bean
nordstrom.com
$74.25
Sporty adventurers, rejoice! You’ve found the perfect topper for all the weekends you’ll spend trekking.
Journeyman Shirt Jacket
Legendary Whitetails
amazon.com
$79.99
A fan of the great outdoors? The rugged style is for you. And this durable, lightweight shirt jacket by Legendary Whitetails, made of sueded cotton with flannel lining, certainly fits the bill.
The Bomber Jacket
Everlane
everlane.com
$98.00
Ah, the bomber jacket. Like many toppers, it traces its history back to the military, and has since been worn by every man about town worth their salt. And if you’re looking to join the club (if you haven’t already), perennial fave Everlane has one that you will most likely wear to exhaustion.
Trucker Jacket
Levi’s
nordstrom.com
$98.00
The denim jacket is just about the trustiest lightweight outerwear option on the market, and in the form of this one from Levi’s—an actual originator of the style—it’s never looked so good.
Brunswick Rain Jacket
If sunny skies aren’t in the forecast, it’s best to have a rain jacket handy. And this no-frills option from J. Crew is just what dependable dudes need to have a bright day.
Cinder Cone Printed Recycled Nylon Jacket
NIKE ACG
mrporter.com
$140.00
Organic Cotton Zip Jacket
SCOTCH & SODA
nordstrom.com
$198.00
Tie-dye is a whole lot of look. In fact, it often comes across as trippy. Scotch & Soda, however, is much more subtle than that. With this twill blouson jacket, for example, the print is streamlined, making it easier for naysayers of the now-ubiquitous style to try.
Flannel-Lined Waxed Hudson Jacket
Flint and Tinder
huckberry.com
$298.00
The field jacket riffs on an iconic military silhouette with functional details galore, including more than enough pockets. Flint and Tinder’s waxed, flannel-lined version packs all the punch of the vintage styles that inspired it.
Camo Finlay Shirt Jacket
Rag & Bone
saksfifthavenue.com
$395.00
Speaking of the military, camouflage jackets are now dime a dozen. But Rag & Bone, a brand that made its name for giving an edge to tried-and-true styles, has raised the bar, adding a camp collar and blurring the print to a pretty cool effect.
G9 Jacket
Baracuta
jcrew.com
$425.00
You pretty much got the gist of James Dean’s iconic red windbreaker (see intro). So, if you’re looking for the right one that captures the essence of Old Holywood, look no further than Baracuta. The brand’s G9 jacket is equally iconic, gracing the shoulders of Steve McQueen, Frank Sinatra, and Gregory Peck.
Airbrushed Workwear Jacket
Marni
saksfifthavenue.com
$990.00
The dependable work jacket takes a walk down the runway thanks to Marni. From the subtle white top-stitching to the high-impact airbrush detail, this topper is for those that like to strut with gusto at their 9 to 5.
Leather Cafe Racer Jacket
Billy Reid
billyreid.com
$1,198.00
Do you constantly feel the need for speed? Look no further than a leather cafe racer. This one by Billy Reid, made of plush lambskin, will kick your fit into high gear.
Leather-Collar Distressed Cotton-Canvas Jacket
Fear of God
matchesfashion.com
$1,395.00
In a relatively short time, Fear of God’s Jeremy Lorenzo has cornered the market on elevated basics. He has punched up the hoodie, made sweats office-appropriate, and offered sports coats that are simply timeless. Of course, his jackets, like this stone-washed and distressed guy, follow the same credo.
Patchwork Denim Jacket
Bethany Williams x The Magpie Project
farfetch.com
$1,430.00
If fun textiles are your thing, Bethany Williams is the name to know. The burgeoning designer has received fanfare for creating collections that repurpose deadstock fabrics, transforming them in a way that feels fresh and cool.
Buttoned Leather Jacket
Bianca Saunders x Future Icons
farfetch.com
$2,341.00
Don’t sleep on Bianca Saunders. The London designer is steadily becoming a resounding voice in fashion. This roomy leather jacket with an oversized collar and cinched cuffs speaks volumes about her design aesthetic.
Herringbone Light Jacket
Bottega Veneta
mytheresa.com
$2,250.00
Oftentimes, it is the simple things that make the most impact. It’s an ethos that Bottega Veneta’s Daniel Lee lives and breathes, and concisely demonstrates with this fitted herringbone jacket.
Barry Samaha
Barry Samaha is the style commerce editor at Esquire, where he covers all things fashion and grooming.
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