PAUSE Highlights: The Tailors Redefining Classicism in the Age of Streetwear

The Renaissance.

With the Met Gala just around the corner and this year’s theme, “Tailored for You,” aligning with the Costume Institute’s new exhibition “Superfine: Tailoring Black Style,” it’s an ideal moment to reflect—not just on fashion’s past and present, but also its evolving future. Tailoring, once the symbol of rigid tradition, is being reimagined by a generation of designers who are rewriting the rules and reshaping what it means to dress with purpose and flair today.

The lines between classic tailoring and streetwear are no longer just blurring—they’re being redrawn entirely. A new wave of designers is bridging heritage and contemporary culture, crafting garments that honour precision and craftsmanship while embracing bold silhouettes, comfort, and cultural expression. At PAUSE, we dive into the visionaries who are transforming tailoring into something personal, powerful, and unmistakably modern.

Dapper Dan

Any conversation about this shift begins with Dapper Dan. In 1980s Harlem, Daniel Day broke barriers by remixing luxury logos onto street-ready silhouettes, long before fashion houses embraced the idea. Shut out of the high-fashion system, he created his own—screen-printing Gucci and Louis Vuitton motifs on custom pieces for hip-hop legends, athletes, and local tastemakers. Though his work faced legal pushback, it sparked a movement. Today, his official partnership with Gucci stands as proof of how far his vision has come. Dapper Dan laid the foundation for today’s high-low aesthetic, where streetwear and luxury are no longer opposites but collaborators.

PHOTO CREDIT: Gabriela Celeste for GQ

Kerby Jean-Raymond

Building on that legacy, Kerby Jean-Raymond of Pyer Moss takes tailoring and streetwear into deeply personal and political territory. His designs weave in Black history, identity, and resistance, using fashion as a platform for storytelling. From sharply cut blazers to relaxed tracksuits layered with meaning, his collections challenge viewers to see clothes not just as style, but as statement. Jean-Raymond proves that tailoring can carry both elegance and urgency—and that streetwear can speak truth to power.

PHOTO CREDIT: Canada Goose

Grace Wales Bonner

Grace Wales Bonner brings a quiet poetry to the mix. Her work is a refined dialogue between European tailoring and Afro-Atlantic heritage, crafting garments that are at once scholarly and sensual. Whether through her romantic Adidas collaborations or her use of rich fabrics and delicate embroidery, she invites wearers into a world where identity and style intertwine. Her designs speak to those who appreciate detail, depth, and a layered cultural narrative in what they wear, that’s why we can’t get over her.

Virgil Abloh

No list of transformative voices would be complete without Virgil Abloh. As the mind behind Off-White and the first Black artistic director at Louis Vuitton menswear, Abloh didn’t just cross boundaries—he erased them. His designs combined architecture, irony, and street codes to challenge luxury’s exclusivity. Whether using quotation marks or collaborating across disciplines, Abloh made fashion a conversation—one that welcomed everyone in. His legacy lives on in the way designers now think about accessibility, art, and what a tailored piece can mean.

PHOTO CREDIT: WWD Media

Demna Gvasalia

Then there’s Demna Gvasalia, whose work at Vetements and Balenciaga turned fashion on its head. Known for oversized silhouettes, irony-laced graphics, and provocative runway moments, Gvasalia fuses streetwear’s attitude with couture-level execution. His tailoring may be deconstructed and exaggerated, but it’s meticulously crafted. At Balenciaga, a boxy suit with football-sized shoulders or a trench that drags to the floor isn’t just fashion—it’s commentary, and despite the controversy he might be surrounded by he has been a trailblazer designer in the modern era.

PHOTO CREDIT: Juergen Teller

Together, these designers are rewriting the language of menswear—and fashion at large. They show that tailoring isn’t about adhering to the past, but evolving with intention. By fusing heritage with innovation, tradition with rebellion, and elegance with ease, they are reshaping what it means to be well-dressed in a world where style is personal, political, and ever-changing.

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