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 a New York-based senior fashion editor who specializes in trend reporting, brand discovery, and the intersection of sports and fashion. She joined Who What Wear in 2021 after almost four years on the fashion team at Refinery29, the job she took after graduating with a marketing degree from the University of Iowa. She has since launched two monthly columns, Let's Get a Room and Ways to Wear; profiled the likes of Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter for WWW's monthly cover features; and reported on everything from the relationship between Formula One and fashion to the top trends from fashion month, season after season. Eliza lives on the Upper West Side and spends her free time researching F1 fashion imagery for her side Instagram accounts @thepinnacleoffashion and @f1paddockfits, running in Central Park, and scouring The RealReal for discounted Prada.
-
No Offense to Trousers, But Gwyneth Paltrow Just Made This "Dated" Denim Trend Look Way More Elegant
I'm sold.
By Nikki Chwatt
-
I'm a Fashion Editor—I Reach For This Effortless Wardrobe Essential When I Don't Know What to Wear
Here are nine easy ways to style the piece.
By Jennifer Camp Forbes
-
Celebs in Their 40s and 50s Are Styling Jeans With This One Sneaker Color Trend
It's probably not what you think.
By Nikki Chwatt
-
Trust Me—This Is the Most Elevated Denim Style There Is
I found the perfect pair.
By Eliza Huber
-
5 Days Into 2025, Kendall and Hailey Already Appointed This the Year's Top Flat Shoe
It makes jeans look so elegant.
By Nikki Chwatt
-
Nicole Kidman's Non-Skinny, Non-Baggy Jeans Are the Ideal Airport Denim Trend
No need to pack any other pairs.
By Allyson Payer
-
Get a Head Start on the Top 2025 Trends With These Key Pieces From the Nordstrom Half-Yearly Sale
You'll actually wear these forever.
By Jennifer Camp Forbes
-
These 4 Winter Trends Look So Chic With Jeans
Perfect pairings.
By Caitlin Burnett