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Everyone has their own personal style preferences, of course. But sometimes our self-imposed rules are meant to be broken. Take Caleigh, a merch master on Team Madewell and light-wash denim devotee. She’d always been hesitant to wear darker denim hues. “I struggle with styling black denim. It ends up feeling a little ‘serious’ for my taste,” Caleigh told us. Well, our styling experts are always down for a challenge—so they put together three outfits that they were convinced would shake up Caleigh’s denim tendencies, without losing her fun, carefree sensibility.


Caleigh wears the Cameron Ribbed Cardigan Sweater, Balloon Jeans and Backcountry Belt.

“The combo of this more relaxed fit with a cardigan for a top felt, easy, playful and great for work.”


Caleigh wears the Bonded Flannel Shirt-Jacket, Men’s Athletic Slim Jeans and the Citywalk Lugsole Lace-Up Boot.

“I was really into the shirt jacket, very fall forward—and the saturated black wash made me feel like I was in slacks rather than jeans. I loved it.”


Caleigh wears the Flannel Oversized Ex-Boyfriend Shirt, Tomboy Straight Jeans and The Kellie Lace-Up Boot.

“I wouldn’t have personally picked this flannel so it was cool to wear something different. Pairing it with washed denim seemed like the perfect balance.”

Thanks for trying something new with us, Caleigh (!). And for the record, our experiment totally worked. Caleigh told us she ended up buying a pair of the black Balloon Jeansright after our shoot. Wanna get in on the obsession? Shop right here.

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