What kind of shoes should you wear for Fall/Winter 2026? With no clear, major trend like the sneaker boom of the past in sight, many men are likely feeling unsure about what shoes to choose. To help you stay one step ahead when selecting shoes this season, we’ve carefully selected five pairs.
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What Signs of Change Are Visible on the Fall/Winter 2026 Runways?”Sharp, Slim Shoes” vs. ‘Round, Chunky Shoes’: How These Opposing Silhouettes Signal a Shift in Trends
In the Fall/Winter 2026 men’s collections, boots with sharp toes and dress shoes with thin soles made an appearance, signaling a shift in footwear trends toward a slimmer aesthetic.That said, this season’s runways weren’t dominated by just one style. Proposals for shoes that boldly emphasized roundness and volume also stood out, with sharp, slim shoes and round, chunky shoes coexisting side by side.
MEN FW 26-27 / PARIS / CLOSE UP / DRIES VAN NOTEN CLP /
MEN FW 26-27 / PARIS / CLOSE UP / DRIES VAN NOTEN CLP /
MEN FW 26-27 / PARIS / CLOSE UP / SACAI CLP /
MEN FW 26-27 / PARIS / CLOSE UP / SACAI CLP /
Although the sneaker boom has already subsided, there are likely many men who have relied primarily on sneakers for everyday wear since the 2010s. The bulk, cushioning, and casual comfort they’ve grown accustomed to over the years are surely not easy to give up.If such a man were to suddenly switch to sharp, slim dress shoes, he might feel a disconnect in terms of visual balance and comfort. With that in mind, we’ve carefully selected five pairs of shoes that bridge that gap, taking into account the sensibilities of men accustomed to sneakers.
Fall/Winter 2026: Shoes for the Man Who’s Ahead of the Curve, Part 1Paraboot “MICHAEL”
Many men who are used to wearing chunky sneakers may find slim-fitting leather shoes lacking in substance.That’s why we recommend Paraboot’s “MICHAEL.” With its rounded toe, three-dimensional U-shaped moccasin stitching, and thick rubber sole, this shoe’s substantial silhouette allows you to enjoy the understated elegance unique to leather shoes without drastically altering the balance of your familiar footwear.
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Fall/Winter 2026: Shoes for the Man Who’s Ahead of the Curve, Part 2JOHN LOBB “TENBY NEW STANDARD”
For men accustomed to the comfort of sneakers, cushioning and ease of walking are non-negotiable factors when choosing leather shoes.John Lobb’s new Fall/Winter 2026 release, the “Tenby New Standard,” meets these needs. This shoe features a simple, open-laced plain-toe design crafted from high-quality calf leather, paired with a thick yet lightweight rubber sole.The “Hilly Sole” used in this design offers excellent cushioning and grip, supporting a comfortable walking experience. Its rounded silhouette adds just the right amount of volume to the foot while striking a balance between the elegance expected of authentic men’s dress shoes and modern comfort—a truly appealing feature.
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3 Shoes for the Man Who’s Ahead of the Curve: Fall/Winter 2026J.M. WESTON & sacai “Derby Golf”
The Fall/Winter 2026 men’s collection featured designs that boldly exaggerated the proportions of derby shoes.Perfectly capturing this season’s mood is the “Derby Golf” collaboration between J.M. Weston and sacai.Based on the brand’s classic “Golf” model, it features a midsole that protrudes significantly around the heel, boldly redefining the shoe’s silhouette. While retaining the traditional moccasin stitching on the upper, it creates a volume that sets it apart from conventional dress shoes.This shoe strikes a balance between a striking presence—one that even men accustomed to chunky sneakers are unlikely to find lacking—and the refined look unique to authentic leather shoes.
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4 Shoes for the Man Who’s Ahead of the Curve: Fall/Winter 2026BOTTEGA VENETA “Haddock Lace-Up Shoes”
Bottega Veneta’s “Haddock Lace-Up Shoes” are a pair that fuses delicate leather craftsmanship with bold volume. The calf leather upper, entirely covered in the brand’s signature intrecciato weave, is paired with a 4.5 cm-thick flatform and a rubber outsole.The contrast between the rich texture created by the intrecciato weave and the thick sole is striking. The appeal lies in its ability to add elegance to an outfit through the craftsmanship unique to a luxury brand, all while maintaining the voluminous look of a well-worn pair of shoes.
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5 Shoes for Men Who Want to Get a Head Start on Fall/Winter 2026New Balance ‘1906L’
With leather shoes gaining prominence, it’s interesting to choose a sneaker that subverts that trend.New Balance’s “1906L” is a model that fuses the “1906”—which has its roots in 2000s running shoes—with a loafer design. While incorporating the classic penny loafer aesthetic, the sole features N-ergy and ABZORB SBS for superior shock absorption.Another appealing feature is the convenience of not having to tie laces.If you want to enjoy the look of leather shoes but can’t bear to give up the comfort of sneakers, this is the perfect pair to satisfy those demanding needs.
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