Baggy Jeans and Sweaters Are My Winter Fashion Staples

Teeny-tiny tops and hot pants may have been celebrities’ go-to summer style, but cooler weather is ushering in an opposite, new fall uniform. Baggy bottoms and loose-fitting sweaters are street style icons like Hailey Bieber and Dua Lipa’s preferred on and off-duty outfits, and the stars make the oversized pieces look surprisingly stylish. 

I knew I wanted to recreate their outfits when I went upstate New York, because while no one wants to look like they’re trying too hard while antique shopping, I didn’t want to stick out among Hudson Valley folks, who have a stealth way of always looking polished even in relatively simple outfits. Not to mention, the formula yields a supremely comfortable, cozy attire that’s perfect for performatively walking around with a coffee in hand and leaf peeping. Ahead, shop my go-to pieces to master this cool girl-inspired outfit. 

5 Cool-Girl Fall Outfit Pieces Inspired by Celebrities

Madewell Perfect Vintage Wide Leg in Harvey Wash

These wide-leg pants are practically the only jeans I’ve worn for the past three months. Aside from being comfortable enough to nap in, they’re loose in all the right places, while remaining fitting in the waist and upper thighs for a still-flattering look. I also like how the darker wash makes them feel more elevated when I wear the jeans with a simple gray crewneck sweatshirt. 

DKNY Fleece Pull-Over Crewneck Sweatshirt

The key difference between this sweatshirt and other versions is its slightly cropped length. The DKNY crewneck sweatshirt has a hem that curves below the waistline, so you’re still showing off your silhouette without ruining the laid-back look by wearing something too short. Opt for the green or white color to make the outfit stand out against a neutral backdrop. 

J.Crew Classic Rugby Shirt

Whether worn alone or layered under an oversized sweater, the multicolored J.Crew Rugby shirt has enough personality to make even my most re-worn outfits seem interesting again.  Since it’s long and a bit boxy, you can style it similar to Dua Lipa, paired untucked with black baggy jeans, or fold the bottom into your bralette for a cropped look.

Cole Haan Yara Soft Ballet Flat

Complementing every oversized, cool-girl uniform are equally comfortable shoes—it could be clogs or even sandals—but the key is to choose something flat with a round toe. I like the Cole Haan ballet flats because their velvet texture meshes beautifully with denim, and looks interesting peeking out beneath a wide-leg pant. Plus, the rich Bordeaux shade helps break up a mostly neutral outfit.

Eddie Bauer Barn Coat

To tie everything together, you need an accessory with a different texture, such as a leather handbag or transitional topper. I usually leave this Eddie Bauer Barn Coat open to show off my sweater underneath, especially since the heavyweight canvas pairs well with other materials like wool and cashmere to create a visually interesting look. Coming in a neutral, dark olive color that matches every wardrobe, it also has a slightly boxy fit that layers easily over anything underneath.

The very best part is that once you’ve nailed down this easy formula, there’s so much opportunity to diversify your outfits simply by mixing and matching a few accessories or opting for a different jean wash. Shop more of my favorite pieces to master a foolproof, It Girl-approved outfit without even trying. 

Levi’s Baggy Jeans

Gap Mid Rise UltraSoft Baggy Jeans

Quay Square Sunglasses

Mavi Jeans Crewneck Sweatshirt