Men's Guide To Styling Oversized Formals: Take Cues From Timothée Chalamet, Jake Gyllenhaal, Jacob Elordi

Among all menswear trends, oversized or baggy fashion remains one of the most debated. The reason is simple: men rarely agree on whether they truly like it or not.

In the 1970s and 1980s, shirts fit close to the body, and people usually tucked them into high-waisted jeans. During the 1990s and early 2000s, styles turned dramatically oversized. When the 2010s Tumblr era arrived, shirts became so tight and buttoned-up that they felt uncomfortable. Today, the cycle has come full circle, with baggy silhouettes making a strong return across shirts and three-piece looks.

If you want to embrace the trend but feel unsure about where to start, take inspiration from celebrities who wear it well.

Jake Gyllenhaal

During the Road House press tour, Jake Gyllenhaal clearly enjoyed experimenting with his looks. At the London premiere, he chose an oversized shirt and layered it with a Prada coat. To keep the outfit relaxed rather than stiff, he finished it with green suede Birkenstock 1774 mules. Why not?

Timothée Chalamet

In early 2025, Timothée Chalamet also appeared on the set of his Bob Dylan biopic, dressed in the singer’s well-worn leather jackets and western boots. He has now moved on to his next major Hollywood role with an entirely different wardrobe. His sharp, polished, retro-inspired suits are pure oversized fashion reference.

Jacob Elordi

When it comes to men’s tailoring, Jacob Elordi champions going bigger. While promoting his lead role in Guillermo del Toro’s Frankenstein, he strongly backs oversized, loose-fitting suits.

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