For a while there, it felt like men’s denim came in two fits: very slim and baggy as hell. Relaxed fits fell out of favor in the early aughts for not being opinionated enough. They were relegated to suburban dads who were okay not standing out for their jeans. Now, though, things have shifted. Not only has dad style become a cult obsession in its own right, but designers are embracing laid-back fits that are just slightly roomier than what you'd get from a straight-leg cut. The latter has become an increasingly popular alternative to too-tight jeans, and designers presumably saw an opportunity to push the envelope a bit.
So how does a modern guy pull the look off without veering into Jerry Seinfeld territory? Daniel Corrigan, co–creative director of Simon Miller—a small brand that's been putting its money on the fit for several seasons—thinks it’s all about the inseam. “We hem all of our M004 jeans at 32 inches to give them more style and edge”, he explains. “I'd say, as a rule of thumb, have it hit at your ankle.”
Jonathan Cheung, head of design at Levi's, also points out that the length of the rise is shorter than it was in the ’90s, and the size of the leg is a little narrower as well. The brand’s newly tweaked 501 CT jean—a tapered version of the iconic 501 fit—is just that. “People had been tailoring their 501s for years,” he told us. “It was one of the most requested alterations at our Levi’s tailor shops, so we simply asked ourselves, ‘Why don’t we do that for them?’ ”
And then there’s the question of how to style them. Cheung points out that, as long as you aren’t rocking a middle-part bowl haircut and a hemp necklace, you’re probably in the clear. “The '90s shirts and haircuts is really what makes relaxed-fit jeans look so dated today,” he explains. “You can wear our classic 501 and 541 fits in a contemporary way, and they look completely different.”
That said, if you're still worried about landing on the wrong side of normcore, try Corrigan’s current uniform: “Light, vintage-wash wide-leg jeans with rips, styled with a pair of Vans and a white T-shirt.” It sounds about right to us (especially in this heat). Because Jerry Seinfeld, as much as we love the man, would never wear Vans.