Milan Fall 2026 Menswear Superlatives

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Remember in high school when the yearbook would come out and there would be all those peer awards like “Most Likely to Succeed,” “Best Smile,” “Cutest Couple,” all that stuff? Well, this is just like that, except there’s no voting and the awards are way more fun than anything those dweebs in yearbook club ever came up with.

Most Camp Use of Faux Fur: Dolce & Gabbana
There are bold fashion statements and then there’s opening your menswear show with a five foot wide faux fur chubby. And that diagonal stripe faux fur pullover (?) with the enormous furry collar/scarf: pure camp. Also, there’s something about that final look with the long gray faux fur coat that feels very reminiscent of Jeff Goldblum as the Big Bad Wolf in Shelley Duvall’s Faerie Tale Theatre. And that’s about as camp as you can get.

Dolce & Gabbana Fall 2026

Dolce & Gabbana Fall 2026

Dolce & Gabbana Fall 2026

Most Likely to Survive a Polar Vortex (in Style): Ralph Lauren Purple Label
No one piles it on quite like Ralph Lauren and this season was no exception. So many luxe layers! One has to feel for those poor models, though. They must have been sweating bullets backstage.

Ralph Lauren Purple Label Fall 2026

Ralph Lauren Purple Label Fall 2026

Ralph Lauren Purple Label Fall 2026

Ralph Lauren Purple Label Fall 2026

Most Surprising Sweater Styling: Etro
A sweater around the waist is one thing, but on top of a suit? We do love a bold styling choice.

Etro Fall 2026

Etro Fall 2026

Of course, Etro also wins the award for Liveliest Prints, but they win that one every season. That said, the intricate pattern they created on that one vest with the delicately placed feathers (below, left) is really something special and deserved a closeup shot without the jacket on top, if you ask me.

Etro Fall 2026

Etro Fall 2026

Etro Fall 2026

Most Voluminous Trousers: Giorgio Armani
“Harem? I hardly know him!” Seriously though, there are few things the house of Armani loves more than a billowy pant, and this season they really went all out. In fact, there’s so much fabric in these trousers you could buy a pair this fall and have your tailor turn them into two pairs of normal pants next spring.

Cuffiest Cuff: Prada
While the suits and coats at Prada got small this season, the cuffs became almost cartoonishly huge. It’s not a look I’m personally prepared to embrace just yet, but I appreciate the foppishness of such a bold sartorial gesture.

Prada Menswear Fall 2026 (Courtesy Prada)

Prada Menswear Fall 2026 (Courtesy Prada)

Prada Menswear Fall 2026 (Courtesy Prada)

Prada also wins the award for the Most Flagrant Use of the Color Purple. That might not seem like a big deal, but Armani has held a vice-like grip on that award for the last 20 years, so it’s actually quite the upset.

Prada Menswear Fall 2026 (Courtesy Prada)

Prada Menswear Fall 2026 (Courtesy Prada)

Prada Menswear Fall 2026 (Courtesy Prada)

Prada Menswear Fall 2026 (Courtesy Prada)

Best Yuletide Dracula: Polo Ralph Lauren
“I vant to suck your blood egg nog!” Admittedly, not the most competitive category, but they definitely won it.

Polo Ralph Lauren Menswear Fall 2026

Polo Ralph Lauren Menswear Fall 2026

Best Casting Get: DSquared2
Securing Heated Rivalry star Hudson Williams to open their show was a stroke of perfectly-timed genius from Canadian fashion provocateurs Dean and Dan Caten.

Hudson Williams for Dsquared2 (Courtesy Dsquared2)

Best Throwback Styling Trick: again, Dsquared2
Are we sagging our pants again? I guess we’re sagging our pants again. True, this feels like one styling trick the Catens never really fell out of love with in the first place, but using suspender holsters threaded through belt loops to sag a pair of puffy shorts over one’s already sagging jeans feels next level.

Dsquared2 Fall 2026

Dsquared2 Fall 2026

Also next level: the volume Dsquared2 is playing with for fall 2026. The fashion world may be all about the Ozempic, but these puffer coats are BULKED UP!

Dsquared2 Fall 2026

Dsquared2 Fall 2026

Dsquared2 Fall 2026

Best Non-Traditional Use of a Tie: MSGM
People barely wear suits anymore, let alone ties. So you gotta give it to MSGM for finding ways to make these fashion relics feel fun again.

MSGM Fall 2026

MSGM Fall 2026

MSGM Fall 2026

Most Likely to Sell: Brunello Cucinelli 
While many luxury brands have seen a steady decline in sales in recent years, Brunello Cucinelli seems to just keep doing better and better. Maybe that’s why so many of the shows this season (not to name names) looked like they were borrowing from Cucinelli’s playbook: tonal outfits, relaxed silhouettes, and a luxurious abundance of layers and cozy textures. For Cucinelli, it’s never really about trends. Their customer doesn’t know or care about those. They just want luxurious clothes that feel good and look great no matter how your style them and that’s exactly what Cucinelli is giving them. This season and every season before. It might not be as exciting as a flattened hat stuck to the back of your coat, but in trying times, classic clothes can be a comfort. And these times they certainly are a-tryin’.

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