It’s time for 'Fit of the Day', where Esquire breaks down the best celebrity street style happening right now.


Preppy fashion is enjoying a renaissance. Not only is it popping up on the catwalks – peep the fall/winter '23 Dior, Etro and Kenzo shows for proof – but the ‘dress down to dress up’ aesthetic has trickled down to streetwear stalwarts through Noah and Aime Leon Dore, too. Whether you’re a fan or not, it’s everywhere. And one piece that has returned to the delight of barrel-chested Twickenham dads is the rugby shirt.

Of course, there are ways to wear it that don't involve getting brutally taken out by a full-back. And you don’t even need a blue passport to harness its power, as shown by the all-American A-lister here.

Who?

Jake Gyllenhaal, a man who, admittedly, can make just about anything look good. He’s known for his fuss-free style, often donning classic tailoring, chunky knits and earth-toned hues.

Where?

Heading into the Jimmy Kimmel Live! Studios, where he spoke about his role in Guy Ritchie’s The Covenant. (No, those italics aren't a mistake. It's actually called Guy Ritchie's The Covenant).

What’s he wearing?

Gyllenhaal has taken cues from traditional prep and incorporated them into a Magliano look that’ll get him from A to B. It's a slightly outsized (read: cosy) and contemporary take on a rugby top, which he has paired with black trousers (spot the drawstring waistband) and classic white trainers. While a Cartier Santos – of which he is the face of – and orange square-frame sunnies add some prestige.

How do I recreate it?

Keep things simple and invest in quality. GANT held a four day exhibition at the beginning of the month, celebrating the American brand’s sportswear heritage and proving its place within prep history. Peruse its website and you’ll find plenty of rugby pieces to snap up.

Mistakes to avoid?

If you’re the type that prefers to not to be spotted in the crowd, stick to Gyllenhaal’s approach and avoid any overt colours. The key is to look like you watch the Six Nations, rather than fancy your chances of playing in it.

YMC
YMC
£250 at MR PORTER
Wax
Wax
Credit: Wax