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DSquared2 Resort 2026 Menswear: Preppy Rebels Rewrite the Fashion Rulebook

by Demos

Forget the rugged wilderness and survivalist tropes of past collections—DSquared2’s Resort 2026 menswear lineup takes a sharp turn away from the Canadian woods and marches confidently into prep school rebellion. Founders Dean and Dan Caten, known for channeling their Toronto roots into rugged and outdoorsy themes, pivot this season to a polished-yet-subversive aesthetic. As they put it, this season is all about “proper, polished rebels”—not rebels with a cause, unless, of course, that cause is impeccable style.

The collection taps into classic Americana filtered through a modern lens. Sharply tailored linen suits are paired with crocheted polos, evoking the golden age of Hollywood with Gene Kelly-like charm. In contrast, distressed denim bombers and casual silhouettes offer a nod to James Dean’s iconic cool, giving the collection an old-school foundation with a Gen-Z twist. These visual cues speak to a deeper narrative of duality: rebellion and refinement, nostalgia and novelty.

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DSquared2 doesn’t stop with the men. The women’s looks echo the same irreverence and bold confidence. Ultra-mini denim skirts cut from utilitarian workwear fabrics barely graze the thighs, while bursts of lace and sheer fabrics inject a raw sensuality. Bralettes and lingerie tops peek from under sharply structured blazers, while zippered denim bodysuits hug the figure like a second skin. These contrasts blur the lines between masculine and feminine, reinforcing the designers’ broader message of self-expression. For Dean and Dan, this gender-fluid mix is more than a fashion statement—it’s a declaration of personal freedom. “The most rebellious act is to dress exactly how you want,” they affirm.

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That message of authenticity reaches new levels with a striking visual tribute: T-shirts, hoodies, and swimwear printed with vintage Polaroids from the 1970s and ’80s by photographer Tom Bianchi. His images—documenting Fire Island’s gay community in its sun-soaked, hedonistic heyday—offer more than retro aesthetics. They reflect a once-radical queer culture defined by openness, art, and resistance. DSquared2 uses these visuals not just as fashion motifs but as cultural touchstones, celebrating freedom of identity in all its forms.

With Resort 2026, DSquared2 reframes rebellion—not through loud statements or utilitarian grit, but through confidence, contradiction, and creative freedom. It’s a stylish revolt where the rules are optional, and the only requirement is authenticity.

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