The 16 Jackets That Will Define Fall 2025, According to Menswear Experts

Spring may bring light jacket season, but fall arguably delivers an even more covetable outerwear occasion: the fateful time of year when two standout silhouettes— bold, oversized topcoats and sharp, cropped jackets—resume their age-old battle for pre-puffer-weather supremacy. The best-dressed guys, of course, are the ones who seamlessly navigate both styles, switching between ‘em without breaking a sweat.

As we approach the crisper months, however, you may be wondering exactly which overcoats and cropped jackets are worth your investment this season. To determine the latest and greatest in men’s outerwear, we asked a handful of menswear pros to share their picks and predictions for fall 2025.

Josh Peskowitz, fashion consultant and creative director

“The big-ass overcoat isn’t going anywhere,” says menswear legend Josh Peskowitz. “Particularly statement overcoats with some texture.” At the moment, his two personal favorites come from Drake’s and Massimo Alba: “It’s gotten relatively easy to find a hefty overcoat, but both brands do them with character and are worth the investment.”

But Peskowitz, as becoming a man of his taste level, is also drawn to plenty of shorter jackets this season. In particular, he’s been coveting Harrington jackets with slouchy, oversized fits—especially the ones from San Francisco designer Evan Kinori and the cult Japanese labels Blurhms and A.Presse. “I think guys are gravitating toward that mix of technical inspiration with workwear or tailored details,” he says. “It’s the juxtaposition of a silhouette that might traditionally be in a technical fabric but made in a textured wool, or vice versa.”

Marcus Allen, stylist and founder of The Society Archive

Marcus Allen is perhaps best known as the sharp eye behind the appointment-only showroom The Society Archive, a vast vintage collection that spans everything from 1960s Abercrombie & Fitch hunting jackets to Tom Ford–era Gucci. As such, his outerwear rotation is riddled with hall-of-fame classics like The North Face’s iconic Nuptse jacket, Ralph Lauren’s sumptuous camel polo coat, and the hardy Barbour Bedale.

Recently, Allen has noticed a slew of style-conscious men layering sporty, technical jackets over more elevated ensembles. “Suiting or trousers with a puffer jacket or a nylon jacket,” he says. That contrast feels modern, relaxed, and—when done correctly—still looks supremely sharp. Allen, for his part, tends to go the opposite route when mixing high-low: “Personally, I look forward to pulling out my overcoats with a gym fit or sweatpants just to grab coffee,” he says.

Jackie McKeown, stylist and design director of Literary Sport

Jackie McKeown, who heads up design for the red-hot athleisure label Literary Sport, didn’t hesitate when I asked for her favorite jacket from the current collections: a sleek and showy blouson with an oversized fit by Auralee. “Specifically in green,” she says. “It’s a sporty silhouette with a cinched waist, but still comes off really clean.” Her styling advice? Wear it without the detachable hood to emphasize the stand collar.

McKeown’s other go-to outerwear brands at the moment are The Row—she especially recommends the quiet label’s takes on the military jacket and denim trucker—and Carter Young, the London-based menswear line by designer Carter Altman. “He’s great at making things that feel familiar, but with subtle details that shift the whole tone,” she says of Altman.

Jasmine Benjamin, stylist and author

“Bombers are coming back again,” says Jasmine Benjamin. “Not that they ever left.” The LA-based author and stylist was especially taken with the vintage Emporio Armani bomber worn by Dominic Fike in his latest video, which was well-worn and rugged but still endlessly elegant.

Beyond bombers, Benjamin sees a broader embrace of utilitarian outerwear on the horizon—think windbreaker-style nylon jackets and minimalist, single-zipper blousons. Some of her top picks this season come from A.Presse, Ernest W. Baker, and Tremaine Emory’s Denim Tears, all of which specialize in classic silhouettes updated with fresh, contemporary details.