Ashley Olsen is so private and allergic to paparazzi, she's rarely photographed outside more than once per business quarter. But when the elusive designer does venture into public, her outfits function like mini masterclasses in stacking runway trends.
Take, for instance, the ensemble she put together for work at The Row's New York office on Mar. 18. Although the luxury brand is known for its elevated minimalist aesthetic, her outfit was decidedly maximalist in nature. Her all-black base layer consisted of wide-legged trousers layered with what appeared to be a trendy black barn jacket. The front patch pockets on her outerwear looked exactly like those found on The Row's Frank Jacket. Around her neck, the street style muse added a lightweight black scarf.
That's pretty much where the simplicity begins and ends. Because on the 38-year-old's arm were not one but two bags from The Row's covetable lineup: a black bowling bag known as the Ingrid and the Ben tote bag in a woven brown leather colorway. This basketweave version of the Ben is sold-out practically everywhere, but the style is still around in smooth black calf leather at several retailers.
The Olsen twins practically invented the idea of stylishly carrying too much in your hands. So it doesn't really surprise me that Ashley Olsen sees the value of the double bag trend. Dua Lipa was also spotted schlepping multiple bags—specifically, a black Chanel maxi hobo bag and a black Hermès Birkin 35—at the airport in January. That said, the trend's roots really trace back to runway shows like Bottega Veneta's Fall 2023 presentation, Miu Miu's Spring 2024 catwalk, and Coach's Fall 2025 exhibition—all where models carried the house's signature bags one on top of the other.
But somehow, the dueling designer handbags aren't even the most controversial element of Olsen's office-bound outfit. Just in time for spring and summer, the fashion mogul has pulled her beloved black City Leather Flip Flops out of storage. Without a doubt, these thong sandals are one of the most polarizing pieces The Row has ever released, in large thanks to their astronomical $890 price tag. Of course, that hasn't deterred celebrity patrons like Kendall Jenner and Zoë Kravitz from copping a pair.
Olsen completed her transitional spring look with a matching black pedicure and a sporty set of black biker sunglasses. Maybe the devout minimalist is finally coming around to the notion that less isn't always more, especially when it comes to accessories.
