You know Levi’s. It’s the San-Francisco-born brand that made denim a global phenomenon. The reason everyone from your artsy aunt to the deli guy to US presidents wears jeans. If all you know of Levi’s is its 501 jeans and its trucker jacket, you’d be just fine. But dig a little deeper into the racks and you’ll find that the 150-year-old label hasn’t been sitting on its riveted pockets.

I say “dig into the racks” and not “scroll a little further” because recently I, GQ’s (self-)anointed denim guy, stopped by Levi’s SoHo location here in New York City. Partly because it’s a nice way to spend part of a workday. But mostly because I wanted to be surprised and intrigued. The internet has pushed brick and mortar stores to the back burner for most people, but when going explore mode, it’s the equivalent of watching Interstellar on the 24-inch LCD TV in your dentist’s waiting room.

At the Levi’s store I found workwear staples and a few surprises hidden in the shadows of the 501—including the just-launched 578 Baggy Jeans, a brand-new silhouette that already feels like an instant classic for the TikTok generation. Inspired (and happy to eat up a few more hours on a Thursday), I threw together four fits.

Look #1: Grand Theft Autumn

In my mind I’m a forlorn indie boy in a rom-com, which goes a long way to explaining my kinship with Rivers Cuomo and everything Joseph Gordon Levitt wears in 500 Days of Summer. Plaid button-ups, graphic tees, jeans—that whole slacker aughts thing just hits for me. This outfit is all of that, helped along by my scene-stealing co-star, a pair of mocha-hued 578 Baggy Jeans. I could’ve layered the flannel over the hoodie for bonus grunge points, but that would be too easy. Besides, the zip-hoodie is back. And also, this is how I actually wear my flannels.

Authentic Full-Zip Sweatshirt

Long-Sleeve Relaxed Thermal T-Shirt

Look #2: Double-Take Double Denim

Pulling off double denim isn’t as difficult as it seems (even for non-self-appointed denim guys and gals). Nail the fit of the pants and the jacket—and there’s all sorts of ways to go, from cowboy slim to skater baggy—and you’re set. As great and irreplaceable as the 501 jean is, I find myself being drawn to the baggier end of the Levi’s spectrum, so I opted for the 568 Loose Straight cut, which fit me like a glove (though not literally).

Matching rinses is a tried-and-true path to double denim dominance, but I think contrasting blues makes the denim two-step a little livelier. Similarly, boots are the obvious footwear choice but might feel like “Yellowstone” cosplay if you’re city folk like me, which is why I went with sneakers. The only canyons here in NYC are filled with Cavas and Blank Streets.

Look #3: Workwear That’s Done the Job

Just about every fashion designer has workwear references on their moodboards, but Levi’s, a blue collar brand deep into its second century, gets to work off of real-deal, ripped-and-stained originals from its archives. As a result, it’s got the goods. This fit—a plaid western shirt tucked into some brawny double-knee work pants, plus an old-school chambray work shirt sized up to wear as an outer layer—still brings its job site credentials, even if your only functioning tool is a laptop covered in band stickers.

Classic Western Standard Fit Shirt

568 Loose Straight Double-Knee Carpenter Pants

Look #4: He Was a Sk8er Boi

This outfit is me healing my inner ’90s child, channeling the days when I mainlined Tony Hawk’s Pro Skater and made questionable decisions on the path to a career that’s fulfilling and also lets me get paid to shop. Levi’s rugby shirt, that grade-school staple, hits the important notes: thick cotton, horizontal stripes. And these self-belted, supremely baggy capri jeans are exactly why it’s worth walking into a store: without trying them on, how would you know that the hem hits at just the right height, delivering primo placement for a white crew sock and roughed-up sneakers?

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