Ashley Olsen Wore the Jeans-and-Flats Outfit Every Cool New Yorker Swears By
Leave it to Ashley Olsen to show up to her birthday party, held at The Grill in NYC, in the most low-key jeans-and-flats combo and still manage to look like the coolest one in the room. To celebrate her 36th birthday, the designer of The Row casually paired a longline black blazer with a white T-shirt, distressed denim, and a pair of suede mocassin loafers—a four-piece combo that every stylish New Yorker just so happens to wear on repeat. Then again, you'd be hard-pressed to find a New Yorker who doesn't, albeit unconsciously, want to dress like an Olsen twin.
But get this: The best part about Olsen's jeans-and-flats outfit isn't just that she's wearing it. Rather, it's how easy it is to copy. Keep on scrolling to add every last piece of the birthday girl's look, from her oversize blazer to her just-distressed-enough jeans, to your year-round wardrobe. As a New Yorker who already owns all four ingredients, I can say with certainty that you won't regret it.
Shop Ashley Olsen's effortless birthday look:
Ripped jeans:
Loafers:
Black blazer:
White tee:
Coming up: Flats and Jeans Work Well Together—These Outfits Are Worth a Try

Eliza Huber is currently the Associate Editorial Director at Who What Wear. She joined the company in 2021 as a fashion editor after starting her career as a writer at Refinery29, where she worked for four years. During her time at WWW, she launched Go Sports, the publication's sports vertical, and published four (and counting) quarterly issues tied to the WNBA, Formula One, and more. She also created two franchises, Let's Get a Room and Ways to Wear; profiled Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter for WWW's monthly cover features; and reported on new seasonal trends, up-and-coming designers, and celebrity style.