Every well-intentioned style-obsessed menswear nerd feels a rush of excitement when the weather cools down. You can find yourself refreshing the weather app like a madman, waiting for the next 70-degree day. Well, my friends, I’m happy to say that day has finally arrived. From crack-out runway looks to packing for summer getaways, we can finally put those warm-weather clothes in the rearview and really start dressing.
With some of our early 2026 trend predictions bleeding into the early fall season—plaid shirts, denim (slimming down), and chore coats—this is the time of year when layering starts to take shape. Although you may not have your cold-weather playbook mapped out just yet, we’re here to help you decipher which indie brands are worth your time, the Swedish label launching its new menswear line, and the slightly dressier approach shoe that could work just as well at a campsite as it could at a dinner table.
While creating a checklist of shops to stop by or signing up for alerts about weekly drops is one way to keep tabs on the latest fall/winter collections, there’s an easier, one-stop-shop for discovering new threads: Mr Porter. We got knee-deep in the newest seasonal arrivals, pulling together seven of our favorite investment pieces. Even the kind your dad, who doesn’t give a shit about fashion, might actually be impressed by.
The Reworked Desert Boots: John Lobb Field Full-Grain Leather Desert Boots
John Lobb
Field Full-Grain Leather Desert Boots
Chelsea boots, work boots, and three-eyelet moc-style shoes, have been what fellas reach for whenever they see the foliage start turning. But when it comes to a footwear category that’s always there for you—like that long lost friend that drops into your life once again—it’s the chukka boot. It’s more unassuming than its counterparts, but when a 177-year-old shoe brand like John Lobb flips the traditional silhouette on its head, it makes the chukka feel even more exciting. From the pebbled-grain leather to the rubber outsole and beautiful dark-brown color, this can seamlessly work its way into your fall wardrobe. Throw on a denim shirt, ecru pants, a camel-colored shawl-collar cardigan, and channel Marvin Gaye in the red beanie for a much-needed pop of color.
