An Easy Guide To Styling Baggy Clothes For An Effortless Look

Think beyond the ‘90s.

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Pernille Teisbaek in baggy pants

The baggy clothes trend is not new to the scene. In the ‘90s, the insouciant attitude of grunge and hip hop culture introduced the now-iconic oversized look. Sagging pants and misfitted flannels and hoodies were imprinted in the era’s rebellious DNA and that influence can be traced in today’s revival. But you might be wondering how to style baggy clothes in a way that keeps you from feeling like you’re swimming in a sea of fabric, and the answer is: proportion.

“Whenever I wear baggy pants, I always make sure that the top that I am wearing is body hugging and usually cropped,” The Folklore founder Amira Rasool tells TZR. Her inspiration? Aaliyah. “She would always wear these baggy cargo pants with a tight crop top. I do it because I like being able to show off my figure a bit even when I’m concealing my bottom half.”

Rasool’s rule of thumb for accessorizing a baggy outfit is to pare it back. “I like to keep the look as minimal as possible because the pants are really the draw and already have so much volume,” she says. “I’ll typically wear a basic flat sandal like a Teva and match it with a tiny bag, like the Telfar mini.”

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Another piece of advice for when styling loose fits may feel counterintuitive: make it fit. "Oversize should be a style choice or the way the garment is cut to fit. Often times we see people in store — especially more petite customers — feeling like they look lost in oversized items,” Shop Le Point Founder Pauline Montupet tells TZR. "The key is to make sure they look intentionally big. So, pants might be loose in the hip and leg, but make sure the waist fits. Or, an oversized jacket — taking up the sleeve or hem a few inches can make a huge difference in something looking intentionally oversized versus just too big.”

Both experts agree that styling multiple baggy pieces in one outfit is not the easiest feat. “Pairing oversized tops with baggy pants isn’t really my thing. The only time that I will do it is when I pair an oversized dress that finishes a bit above the ankle with oversized wide leg pants that peak out a bit beneath the dress,” Rasool says. “The trick is that the pants can’t be so baggy that they look bulky under the dress you’re wearing. The pants usually need to be more of a wide or straight leg fit at the bottom to pull it off.”

Bottega Veneta Spring/Summer 2022
Balenciaga Spring/Summer 2022

As for Montupet, a successful oversized layering moment also ties back to this idea of fit and proportion. “It's a bit harder to do baggy on baggy to create that juxtaposition of proportion, but it is doable if you keep these two main things in mind to make it work. First, keep it polished — so make sure items are big but tailored correctly and second, add a touch of skin — a little collarbone, leg or ankle can help break up all the fabric.” Ahead, a handful of recent baggy looks that are worth a repeat and where to shop the best oversized pieces.

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With A Cropped Cardigan

As Rasool pointed out, an easy way to quickly style a pair of baggy pants is with a form-fitting top (bonus points if it’s a bit cropped).

Monochrome Moment

Winter whites are made slightly cooler when worn in a voluminous silhouette, as illustrated above with this puffer and pants duo.

Play On Texture

Incorporating multiple textures into one outfit takes things up a notch, and the contrast between a leather bomber jacket and nylon cargo pants is oh-so-good.

Paired With Something Sweet

Once temperatures thaw a bit and spring’s arrival is closer (almost there!), a lovely way to transition your floral dresses from winter to the new season is by layering an oversized jacket on top.

Statement Outerwear

If baggy pants or a jumbo size top just doesn’t feel right for your personal taste, an oversized jacket will always do the trick (and tends to feel easier to style).

Oversized Tee, Please

A baggy graphic tee worn with your favorite separates (a leather jacket and pleated skirt, perhaps?) is a fresh and stylish way to approach the oversized trend.

Going-Out Staple

Going-out tops and baggy jeans is the new outfit formula du jour, and that’s sure to only pick up momentum in the coming months.