MILAN – The fall 2026 shoe game at Milan Fashion Week mirrored menswear’s broader return to polish classicism. From reworked heritage styles such as derbies and loafers to outdoors-inflected styles and sharpened Chelsea boots, footwear grounded the season’s heritage roots while adding contemporary twists.
Classics Reinvented
Menswear classics were back in fashion on the Milan runways for fall 2026. The tailored topcoat was the star of the season, but what’s the ultimate footwear to pair it with, next fall?
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Heritage designs from polish lace-ups to loafers were ubiquitous, reinvented with modern twists. These ranged from Prada’s colorful laces on derby styles to match the utility capes over standard trenchcoats to Brunello Cucinelli’s subtly distressed suede iterations and Giorgio Armani’s chunkier version with a laid-back and casual allure. A men’s staple since the ‘90s, they were often unveiled under sartorial pants but would work handsomely with denim, too.
Loafers emerged as strong alternatives, seen on the Ralph Lauren catwalk under Purple Label looks in traditional iterations – from bowed, patent styles under a tuxedo to tassel-bearing cognac suede ones under said topcoat. Etro updated them with thicker soles, Paul Smith using distressed leather and adding a buckle, while Giorgio Armani had novelty interpretations featuring an oversized Velcro strap enveloping the feet.
Hiking Boots
The Winter Olympics’ craze that is sure to hit Milan next month trickled down to runway collections and fall 2026 presentations, with a lot of sport references, and, most importantly, nods to an active lifestyle in the great outdoors.
If Dsquared2’s Dean and Dan Caten went all in, parading a winter sports-inspired collection and bringing heat to the slopes with their futuristic wedge ski boots for women and Western boots layered with detachable covers nodding to ski boots for men, others played a safer game tapping into the mountaineering aesthetics.
At Ralph Lauren suede hiking boots with colorful laces and higher, mixed-media version inspired by snowboard boots abounded, accessorizing many of the Polo looks that opened the show. Brunello Cucinelli went for more subdued iterations, offering distressed leather versions with tonal laces, while Giorgio Armani’s versions befitted après-ski attire.
Chelsea Boots
Chelsea Boots were having a moment in Milan, updated with slightly pointier toes as seen on the Paul Smith catwalk done in polished leather to accessorize flannel business suits or velvety suede and black leather at Brunello Cucinelli, the latter worn under straight-leg jeans. The design appeared also in the Saul Nash fall collection, the result of a partnership with Manolo Blahnik.