The Men’s Jackets to Upgrade Your Autumn Wardrobe
Choosing the right jacket is a strategic decision that says more than you might think.
There was a time when “fall jacket” meant you were either dressing like your dad or your old RA: oversized windbreakers, sad trenches, maybe a fleece vest if you were feeling bold. But those days are gone. Today’s outerwear landscape reads more like a design lab: chore coats laced with military-grade fabrics, cashmere overshirts cut like blazers, fleeces embroidered like couture. It’s less about warmth and more about signaling—are you the guy who layers Loro over technical cargos, or the one who shows up in a Miu Miu zip-up like it’s 1998 all over again?
The category has expanded far beyond utility. Jackets are now style shorthand. They tell people how you see yourself: low-key luxury loyalist, vintage-sourced purist, streetwear maximalist, or maybe just someone who refuses to look cold or clueless. And while the world of men’s fall outerwear is riddled with brand landmines—too much Gore-Tex and you’re glamping-adjacent, too much leather and you’re channeling “divorced dad joins a band”—there’s a middle ground deserving your attention.
That’s where this lineup comes in. It’s a cross-section of what fall 2025 looks like from the front lines: high-design bombers, off-duty luxury fleeces and jackets you’ll wear from subway to summit. Some are investments, others are next-level upgrades. But all of them are engineered to help you sidestep the worst offense in fall style: looking like you didn’t think about it. Let’s get into it.
There’s a particular kind of day—when it’s too crisp for a tee and too mild for a coat—for which this overshirt proves its worth. Cashmere and mohair lend it warmth without bulk, while the check pattern reads more Milanese espresso bar than pumpkin patch cliché. Toss it on over a hoodie or under a trench, and it adapts. The texture is what gets noticed, not the label (though you’ll still want to name-drop it).
The Relwen Windzip is for those transitional days when it’s 55 at sunrise and 72 by lunch, and you just don’t have time to change twice. It’s cut like your favorite midweight jacket but built like technical gear, with down-alternative fill, a water-resistant shell and enough stretch to handle everything from morning commutes to trail detours. The tall stand collar keeps your neck warm when the breeze picks up on the walk back from the dog park, while hidden tricot-lined pockets save your hands when you forget gloves (again).
You could call this your off-the-grid jacket, but that would undersell how good it looks in a city with cell service. The Clark Bomber takes the WWI aviator silhouette and filters it through a moleskin lens—soft, brushed, and tailored with just enough drape. It’s unlined, which means it wears like a fall shirt jacket but still holds its own when the sun dips.
Imagine an heirloom sweater engineered into outerwear. The handfeel here is absurd, like someone spun a campfire in silk. It’s structured but plush, elegant but unfussy. Wears like something your better-dressed friend would loan you “just for the weekend,” and then conveniently forgets to ask back.
Let’s say you’re ducking out for a corner-store run, but there’s a 40 percent chance of a friend texting “drinks?” halfway there. This fleece is your buffer. It’s cut with enough finesse to make it fashion-adjacent, but cozy enough to sleep in. The logo’s there, but it’s not glaring. Picture it as your off-duty armor, best paired with jetlag, espresso and a swipe of pomade.
For the days when your plans (and your weather app) can’t seem to commit. This double-weave jacket feels like a vintage army surplus find—if that surplus had better tailoring and Belgian design sensibility. The twill trim adds edge without overthinking it. It’s the kind of outer layer that looks just as at home in a Brooklyn bookstore as it does under a Paris café heater.
This one’s for when fall starts really getting photogenic. Maybe it’s the leaves, maybe it’s your playlist. The cropped boxy cut adds posture, while the embroidered anagram at the chest whispers luxury. It’s sharp but playful, like your friend who gets stopped at parties not for what he’s wearing, but how he wears it.
Call it the unpredictable weather jacket. The technical fabric shrugs off drizzle, while the checked pattern brings just enough irreverence to contrast your most grown-up pants. Functional drawstrings keep the silhouette flexible, whether you’re riding the subway or hopping a budget flight to Lisbon with zero checked bags.
Designed for actual weather, not just vibes. This one’s for those 47-degree mornings when your car’s windshield fogs, your phone is at three percent, and you still haven’t had coffee. The water-resistant shell, corduroy collar and padded insulation are the right mix of Americana and practicality. It’s fall-coded, sure, but without going full leaf-peeper.
This is the jacket version of the Uber XL you didn’t know you needed. Oversized without feeling clownish, black without being boring and weirdly flattering on everyone. The vibe? You’re coming from somewhere important, even if it’s just the gym. Best styled with confidence, headphones and a tight schedule.
This overshirt is like a minimalist reset button for your wardrobe. It’s what you reach for when everything else feels too designed. The wool-linen blend regulates body temperature like a passive house, and the silhouette flatters without trying. Clean, cool and slightly androgynous, this overshirt says “editorial” without saying much at all.
Think “vintage chore jacket” but built for the kind of gear-carrying lifer who needs a fabric that refuses to quit. This isn’t your run-of-the-mill denim—it’s 12 oz Kaihara Japanese slub, woven with Cordura nylon, meaning it takes every knock, brush and abrasion like a champ. Wear it over a tee on laid-back Wednesday afternoons, or pull it on over a heavyweight hoody when you’re assembling camp chairs on the tailgate.
Straight outta Seoul, with a nod to military heritage, FrizmWorks M65 is a rebel with a cause. This shape-shifting wonder plays both sides of the men’s fashion field—outerwear star and mid-layer maven. Reinforced elbows and a fortified placket make it tougher than a drill sergeant, while ribbed cuffs and sneaky snap closures keep the elements at bay.
Meet the polymath of outerwear. Loro Piana’s Icer Jacket, part of the brand’s C.O.L.D. line, has been tested as rigorously as Olympic athletes to protect the wearer from cold weather. The Storm System-treated cashmere exterior offers an unbeatable combo of softness and weather resistance. Interchangeable collars let you pivot from alpine to urban without missing a beat.
Moncler’s two-faced, full-zipper jacket is for the chronically indecisive with deep pockets. Can’t choose between two looks? No problem, just flip it inside out. At this price, you’re not just buying a jacket; you’re buying the right to complain about being cold while looking like you have a membership to the Yellowstone Club.
Chameleon-like in its versatility, this Eleventy Milano overshirt-style masterpiece morphs from casual to classy faster than you can say “brunch reservation.” Its off-white hue is a blank canvas for style mavens, while the spread collar stands ready to frame your face or flip up against the wind.
Buck Mason created a coat for guys who want to look rugged but have never changed a tire. This twice-boiled blazer-inspired wool number is like wrapping yourself in a really fancy blanket. Those horn buttons are real, unlike your plans to actually learn woodworking. Pair it with raw denim and boots for peak city lumberjack vibes.
Drake’s managed to make a jacket that says “I enjoy the outdoors” without actually requiring you to go outside. The olive green waxed cotton will age better than your jokes on X, while the corduroy collar adds a scholarly touch. That hidden pocket? Perfect for stashing your phone when you pretend to be “one with nature” on social media.
Theory took the blue-collar trucker jacket and sent it to business school. It’s stretchier than your excuses for skipping the gym and more versatile than your dating profile. Ideal for casual Fridays when you still need to look like you might fire someone.
Mack Weldon’s reversible puffer is like having two jackets in one. Thinsulate technology ensures you’re snug as a bug, while the choice between a sleek herringbone or a rugged quilted exterior keeps your style game strong. Water-resistant and ready for action, this full-zip jacket is a true chameleon of the wardrobe, and is ideal for that pre-down jacket weather.
Overland pays homage to the iconic WWII sherpa shearling jackets with their classic bomber. The genuine British Merino sheepskin and durable Nappa finish exterior are a match made in heaven, ensuring you’re cocooned in comfort and timeless style.
This hoodie is a fortress against the elements, crafted from premium materials to ensure you stay warm and dry. The adjustable drawstrings and sleek hood provide adaptable protection, while the invisible zip pocket is so useful, for the ultimate in versatility within your wardrobe.
Valstar always showcases Italian craftsmanship at its finest. Made from luxe pure cashmere fabric bonded with a waterproof membrane and lightly padded for extra warmth, this navy jacket blends style and functionality. The design stays true to the original A-2 flight jacket, providing a timeless look.
Made of Martexin 10-ounce sailcloth, this timeless work jacket, via Huckberry, is designed to fend off cold and wet weather, while developing a handsome patina over time. The quilted, flannel-lined interior and insulation of this American-made workwear waxed jacket provide heaps of warmth, and offer a great alternative to the usual denim jacket.
Barbour updates a classic: Based on the popular Chelsea Sportsquilt jacket, this version features a lighter weight construction, classic equestrian styling and a quilted funnel collar, providing a stylish and comfortable option for the warmer months.
The Best Men’s Jackets for Fall
Loro Piana Ambrose Checked Overshirt
Relwen Windzip Jacket
Taylor Stitch The Clark Bomber
Gabriela Hearst Cashmere-Alpaca-Silk Jacket
Celine Homme Logo-Embroidered Fleece Jacket
Dries Van Noten Cotton Jacket with Twill Trim
Loewe Anagram Wool-Cashmere Jacket
Miu Miu Checked Technical Jacket
Polo Ralph Lauren Quilted Shell Field Jacket
Entire Studios Oversized Bomber Jacket
Jil Sander Wool-Linen Overshirt
Gramicci Japanese Slub Denim Jacket
FrizmWorks M65 Field Liner Jacket
Loro Piana Icer Jacket
Moncler Vallorch Reversible Down Jacket
Eleventy Milano Boiled Wool Shirt Jacket
Buck Mason Felted Chore Coat
Drake’s Corduroy-Trimmed Waxed-Cotton Jacket
Theory River Trucker Jacket
Mack Weldon Warmknit 2-Way Puffer Jacket
Overland Classic Sheepskin B-3 Bomber Jacket
Nobis Hedge Men’s Performance Hoodie
Valstar Valstarino 2 Layers Soft Cashmere Jacket
Flint and Tinder Flannel-Lined Quilted Waxed Rancher
Barbour Flyweight Chelsea Quilted Jacket
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