On March 19, 2024, Jake Gyllenhaal stepped out of a car and into a fashion flashback.
He was clad in a loose-fitting grey blazer layered over a baby blue shirt that barely concealed the tight-white vest beneath it, itself struggling to contain a profusion of chest hair bursting proudly forth. On his legs were a pair of light blue jeans, neither tight nor baggy. And on his feet were a pair of well-shined burgundy Oxfords.
Gyllenhaal was in New York City for an appearance on Good Morning America. From where he’d come, however, only he and his driver know.
It could have been the eighties, where his double-breasted jacket's looser fit would have felt perfectly at home amongst the broad shoulders and bold silhouettes that defined power dressing of that era.
It could have been the nineties, where the unbuttoned shirt, hint of a white vest and blue jeans whispered of grunge icons, de-emphasised silhouettes and a general sense of studied nonchalance.
The Oxfords, of course, gave little away having been a staple of men’s fashion for easily a century, though they wouldn't have felt out of place in the noughties when sleek, lace-up dress shoes found favour for a more polished take on casual wear.
But the key here was the update. The blazer's relaxed silhouette avoided the shoulder pad excesses of the eighties, and the jeans were neither the acid wash of the nighties nor the skinny fit of the tens.
The look is, in fact, a masterful blend of past trends, brought current with a modern understanding of fit and proportion. It's a look that says, “I know my fashion history, but I'm also comfortable in my own skin (and decade).”
Looks like this are what have thrust Jake Gyllenhaal into style stardom. He's no longer just your run-of-the-mill multimillionaire actor; he's a multimillionaire actor who knows not only how to play a part, but how to look the part whilst doing it.
And with the Amazon spring sale now on, this is the perfect time to pull this look together at a fraction of its usual cost.
