A Week of Outfits: Piper Gray

Piper Gray, a copywriter at Warby Parker, lives on the Upper East Side of Manhattan and has awesome style. “I think I have a magpie tendency,” she told us. “If it’s colorful or bright or shiny, I’m automatically intrigued.” Here, she shows us five fun outfits she wore in a week…

A Week of Outfits: Piper Gray

Denim halter dress: Gap. Scarf: travel souvenir. Sunglasses: Warby Parker. Tote: Loeffler Randall. Helmet: Bobbin. Shoes: Anthropologie.

“Every fall, I toy with the idea of getting a uniform. I think, maybe this is the year! But I know I’d get bored with that. Still, there are pieces that repeat frequently — like this denim wrap dress. It’s backless, so I cover up with a scarf at work.”

A Week of Outfits: Piper Gray

Shirt: COS. Skirt: Old Navy. Sandals: similar. Bag: ban.do. Sunglasses: Warby Parker.

“I wear a lot of bright colors, and I joke that the day that I start to wear all black is the day I should leave New York. I’m from the south, so I don’t have that urbane approach to dressing. I do love black-and-white graphic stuff, though, because it looks great mixed together. The skirt is from Old Navy, which, by the way, has been killing it recently. I was looking through their sale rack, and it was a $9 find. It has that Mad-Men-esque vibe to it. The silver bag is actually a lunchbox!”


A Week of Outfits: Piper Gray

Shirt: similar. Pants: similar. Pink shoes: Nasty Gal. Backpack: Herschel, with a Pucci scarf. Sunglasses: Warby Parker.

“On my bike, I always feel like such a goober with my backpack and helmet on. Obviously, I’m all about safety, but it’s hard to feel that cool when you’re loaded up with everything. So, a gold helmet was one way to add my flair. I catch glimpses of my reflection passing by building windows, and I’m like, oh, yeah, that’s definitely vibrant. Since my backpack is super utilitarian, I tied on a Pucci scarf to dress it up. It was on sale at a boutique in Memphis, and I thought, this is my chance to get one.”


Chambray blouse: similar. Black pants: Loft. Sunglasses: Warby Parker. Tassel earrings: Hart Hagerty. Tote: Loeffler Randall. Sneakers: similar.

“My running shoes are black and white polka dot. I hate hate hate the phrase ‘classic with a twist,’ but they are classic with a twist. Since I bike to work, I wear Nikes or ratty white Supergas with the grand hope of changing into nicer shoes when I get to the office. But, I have to admit, more often than not I end up leaving them on all day.”


Dress: vintage DVF. Moto jacket: simliar. Bag: ban.do. Sandals: similar.

“After my grandmother died, we discovered a never-been-worn floor-length Diane Von Furstenberg dress from the 70s in her closet. The tags were still on. I’m the only grandchild in my family, so no one else was clamoring for it. I took it to a tailor and got it hemmed shorter. My college roommate used to call the print ‘TV static.’ It’s a special piece to me, and I like that it doesn’t feel frozen in time.”

Thank you so much, Piper! Your style is wonderful.

P.S. Five more outfits we’d love to copy, and a trick for making mornings easier.

(Photos by Ana Schechter for Cup of Jo.)