7 Fall Menswear Upgrades That Live up to Their Pedigree

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 BootsJohn LobbField Full-Grain Leather Desert BootsChelsea 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.Mr. PRibbed Wool and Cashmere-Blend CardiganMargaret Howell MHLMHL. Naval Straight-Leg Cotton-Drill TrousersApproach Shoes Good Enough for Aperitivo: Diemme Bardolino Suede and Leather SneakersDiemmeBardolino Suede and Leather SneakersCapital-F fashion brands have adopted the approach-shoe, but it’s always nice to see an outdoor shoe brand riff on what a dressed-up approach shoe could look like. Diemme takes the guesswork out of it with its version, which kind of reminds me of a low-top Air Jordan 12, just with Vibram outsoles and the ability to handle a scramble over some rocks. Playing off the black shoes, we paired them with faded black denim (shoutout to charcoal-jeans god Richard Gere), a thermal, and a hit of green from every menswear circle’s favorite label, A.Presse, for added texture.A.PresseVintage Cotton-Jersey Zip-Up HoodieAaron LevineWaffle-Knit Cotton SweaterJeanericaVega Straight-Leg Recycled Cotton-Blend JeansCorridorNew York New York Embroidered Cotton-Canvas CapA Toasty Cardigan: Casey Casey Panno Wool-Knitted CardiganCasey CaseyPanno Wool-Knitted CardiganNo autumn clothing rotation is complete without at least a tinge of pumpkin-cinnamon-nutmeg-hued knitwear. This one from Casey Casey is cut from virgin wool, which means it’s untreated and naturally antimicrobial, so you don’t need to wash it so often. I like going with a pale-blue corporate button-down underneath, tucked into a relaxed-fitting pair of jeans and brown derbies. It’s a kit that can be worn while leading a roundtable on moodboards or while sitting in a number-crunching cubicle.MfpenGenerous Cotton-Poplin ShirtGraphpaperSelvage Straight-Leg JeansGeorge Cleverly3cm Suede BeltMorjasThe Split Toe Full-Grain Leather Derby ShoesFull-Grain Leather Flyness: Valstar Smith Shearling-Trimmed Full-Grain Leather JacketValstarSmith Shearling-Trimmed Full-Grain Leather JacketEveryone needs an Ahh Shit leather piece. I would fully expect you to cue up Lil Wayne’s "My Leather So Soft" as you get dressed. Throw on a long-sleeved polo shirt, blacked-out corduroys, and a chunky moto boot to help swag up the shearling-trimmed leather jacket. And to really commit to flight mode, you obviously need a pair of aviator shades.John SmedleyCaverhill Knitted Merino Wool Polo ShirtThe RowRamil Straight-Leg Cotton Corduroy TrousersVinny'sMoto Leather BootsCutler and GrossGR14 Aviator-Style Acetate SunglassesThe Cord and Cashmere Combo: Dries Van Noten Straight-Leg Cotton-Corduroy TrousersDries Van NotenStraight-Leg Cotton-Corduroy TrousersDries is a brand you lean on for interesting colors and patterns, but there are also plenty of more subdued pieces from the label, where the craftsmanship is still there but the clothes blend into your everyday wardrobe effortlessly. You can wear these cords with a soft cashmere sweater, quilted army-green gilet, and a pair of trusty 993s, which your impending plantar fasciitis will thank you for.Ghiaia CashmereCashmere SweaterBlue Blue JapanCotton-Jersey T-ShirtRRLCooper Quilted Shell GiletNew BalanceMIUSA 993 Suede, Mesh and Leather SneakersThe Damn Good Denim Jacket: Visvim Denim JacketThere’s a batch of exciting Japanese labels sprouting through the cracks of menswear, but Visvim still remains one of the best thanks to its steadfast approach to menswear. Take a gander at the brand's Type I denim jacket, which is on par with the OG, with one pocket and the back buckle for adjusting the fit. The difference is in Visvim’s whiskering and fading process, which is where the investment starts to show. Throw on a V-neck sweater underneath, along with olive-colored cargo pants and a pair of Common Projects—not the Achilles Low, but their buttery-suede driving sneakies.AtonCotton and Yak-Blend SweaterNN07Jett 30026 Embroidered Organic Cotton-Jersey T-shirtFrizmworksWide-Leg Cotton-Twill Drawstring Cargo TrousersCommon ProjectsWinter Driving Suede SneakersThe Shadow-Plaid Swerve: Our Legacy Moss Checked Cotton-Flannel ShirtOur LegacyMoss Checked Cotton-Flannel ShirtNot sure where to freshen up your fall rotation? A soft-ass shadow-plaid flannel will do the trick. Our Legacy makes much more than its beloved Camion boots and Third Cut jeans. Lean all the way into the workwear tip with this one: throw on a suede chore coat, straight-leg jeans, and a pair of Engineer boots. The best thing about this flannel is its versatility. You can wear it now over a T-shirt or waffle-knit thermal, or use it as a mid-layer under a bomber jacket.Drake'sWelder Suede Chore JacketOrslow101 Straight-Leg JeansRed Wing2996 Engineer Buckled Leather BootsLe Gramme19g Punched Ribbon Recycled Sterling Silver Cuff