Picture this glamorous sight: I’m walking to grab a salad during my work lunch break last week, and the hemline of my baggy jeans are dragging across the dirty New York streets. Across my shoulder is a giant Peter Do bag, which could easily fit a corgi or a beagle. My outfit is hard to miss—it literally takes up space—and I can feel the stares of strangers from all angles. Of course, they don’t know that I’m test-driving the oversized style trend that’s been taking over the runways and being embraced by stars like Justin Bieber, Hailey Bieber, and Bella Hadid. To them, I am simply someone who is swimming—perhaps drowning—in supersized fashion.

On the runways, brands like Balenciaga, Peter Do, and Marc Jacobs have all shown XXL shapes in pieces like denim, dresses, and suiting. It didn’t take long for the look to catch on among A-listers. Justin Bieber went viral at this year’s Grammy Awards when he showed up in a huge Balenciaga suit complete with Crocs. Celebrity stylists have been seeing an uptick in their clients coming on board with the spacious look, too. “We’re seeing a return of ‘90s trends in general, and we really love to see the reemergence of hugely oversized pieces—they can be so fun to play with,” says Zadrian Smith of the stylist duo Zadrian + Sarah, who currently dress stars such as Ariana DeBose. 

Intrigued by these commanding silhouettes, I wondered if I—a non-celebrity—could pull off the bold look. As someone who was a devoted skinny jean wearer during the 2010s, a humongous pair of jeans is extremely out of my comfort zone—but my fashion resolution this year was to experiment more. So, armed with my jumbo clothes and bags, and with the help of advice from three pro stylists, I embraced going baggy for a week below. Turns out, there are tips and tricks to nailing the look—including knowing which pieces to invest in, nailing layers, and considering proportion. “All of these styling choices keep someone from drowning in the clothes,” says Smith.

Jeans are the perfect entry point.

Skinny jeans were officially declared over by Gen Z in 2020, and this summer it’s all about the baggy fit. Bella Hadid wore an impeccable pair after the Balenciaga couture show in Paris this month. If you think about it, big denim is the perfect entry point into the oversized trend: It’s a versatile, wear-with-everything piece. Pair it with a tighter-fitting white tee (or a cropped one like Bella’s), and you’ve got a strong look. “The key to oversized jeans is they need to be really big throughout, except for the waist,” says Thomas Christos Kikis, who styles Gabrielle Union. “If you’re feeling overwhelmed by the proportion, throw on a heel—a little bit of height and glamour help to offset the volume.” While test-driving a pair of widened Closed x Michael Philouze jeans, I found them giving my work button-ups an instantly cool, effortless feel. They’re slightly more current and edgy than your standard straight-leg or skinny jean.

A huge bag is, above all, very practical.

Carting around a giant Peter Do Dumpling bag for the day, I was worried the hefty crossbody might make my back give out. But, surprisingly, the jumbo style (while a tad heavy) was not only comfortable to carry, but it could also fit anything I could possibly need for a busy work day. Too often, I’ve sported cute mini bags that only fit my keys and lip gloss. Now, I could actually cart around a laptop, all my chargers, water, and even a change of clothes to work out after with ease! You don’t have to go that big, though: A smaller hobo bag, like the tan style that Zoë Kravitz wore back in April, nails the feel of the supersize trend in a more manageable way. “Small bag fatigue is starting to settle in,” agrees Kikis. “People are out again and they have stuff! The Fendi Spy bag era is upon us, and I’m ready.” 

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