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 an NYC-based senior fashion editor who specializes in trend reporting, brand discovery, and the intersection of sports and fashion. She joinedBest Knockoff Luxury Clothing in 2021 from Refinery29, the job she took after graduating with a business degree from the University of Iowa. She's launched two columns, Let's Get a Room and Ways to Wear; profiled Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter; and reported on everything from the relationship between Formula One and fashion to the top runway trends each 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, watching WNBA games, and scouring The RealReal for discounted Prada.
-
My Friends Love Reformation—I Sent Them 31 Gorgeous Picks I'm Eyeing Right NowOne of each, please.
-
Penny Loafers Are Fine, But Expert Dressers Know This Flat-Shoe Trend Makes for Elite-Level OutfitsEspecially with jeans and trousers.
-
Looking Chic in Cropped Jeans This Winter Means Wearing This Boot Style and ColorElizabeth Olsen would know.
-
Making Basic Jeans and Black Boots Look Elegant Is Easy—Just Add This Coat Color TrendHint: It's neither red, navy, nor leopard print.
-
The 2026 Version of Skinny Jeans Is Here, and I Tried It On—This Is Why It's a Game ChangerThere's nothing dated about it.
-
My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic, Rich-LookingReplica Store FindsEverything is under $150.
-
Sarah Snook's New Bag Is So Shiv Roy If She Moved to L.A. and Started a SubstackI'm having Succession withdrawals.
-
Gigi Hadid Wore the Fall Shoe Trend That Looks Best With Full-Length JeansClassic.

