Men’s baggy jeans are no longer a thing of the ‘90s and 2000s or reserved solely for skaters. If you haven’t heard, those decades are trending hard right now which means that the fashion pendulum has swung back toward wide-leg territory with every designer trotting out bigger, baggier silhouettes on the runway and stars like Justin Bieber and Shai Gilgeous-Alexander strutting the streets and NBA tunnels in leg-swallowing jeans. And before you chalk up the trend as just a sliver of the conversation relegated to high-fashion, major brands like J.Crew and Gap are riding the wide-leg wave to sell-out results.
Apart from a classic straight leg, a la the almighty Levi’s 501, baggy jeans might just be the most versatile silhouette there is. High-waisted with a crisp white tee tucked in, or worn low on the hips with an oversized button-up, the right pair can play multiple roles. Worn with a gentle break, a pair of baggy jeans can drape over your shoes in the most rakish way, adding a refreshing relaxedness to your silhouette. You can pair them with some equally beefy shoes for a certified Big Fit or play with contrasting proportions with a pair of low-profile sneakers or loafers. But don’t confuse baggy with sloppy—done well, a pair of baggy jeans can look more elegant than you’d think. If you crop them just so, they can take on a crispy clean aesthetic on par with a well-tailored suit, while giving your shoes the space to shine. In other words, there’s a whole universe of men’s baggy jeans out there, and we’ve cherry picked the stars right below.
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