Ashley Olsen Pairs the Double Bag Trend With The Row's Polarizing $890 Flip Flops

The elusive designer made a rare foray into maximalist styling with an accessory-laden work outfit.

Ashley Olsen in New York City carrying the double bag trend with a pair of her The Row flip flops
(Image credit: Elder Ordonez/INSTARimages)

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.

A photo of Ashley Olsen styling two bags from The Row with the brand's black leather flip flops.

Ashley Olsen styles two bags from The Row with the brand's black leather flip flops.

(Image credit: Elder Ordonez/INSTARimages)

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.

a model carrying two bottega veneta bags on the runway to illustrate the double bag trend

Bottega Veneta's Fall 2023 show featured women carrying two bags instead of one.

(Image credit: Getty Images)

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.

Hanna Lustig
Staff Writer

Hanna Lustig is a staff writer at Marie Claire, where she gets to gab every day about the topics she holds most dear: fashion, beauty, and celebrity. Hanna’s editorial journey began with formative internships at Elle and InStyle, where she was lucky enough to work for some of the smartest women in media while she was still in college at the University of Tennessee. Hanna then accepted a digital culture reporting fellowship at Insider, where she helped carve out a new beat dedicated to covering influencers. Those experiences later served her well as a staff writer at Glamour, where she developed a knack for spinning quick turnaround celebrity news and trend reporting into juicy feature stories. Some of her greatest hits include an earnest ode to the no-pants trend, this meticulously reported feature exploring the rise of endoscopic facelifts, this snappy take on the Chanel-designed fantasy of Sofia Richie’s wedding, this tribute to WAGs past and present, and this timeline of Katie Holmes’s life and career as told through her denim collection.

Diane Keaton once hung up on Hanna during an interview, but thankfully that mishap did not derail what has otherwise been a deeply fulfilling career writing for and about women. As one of Marie Claire's resident experts on style and culture, her current coverage ranges from exploring TikTok's contrast makeup theory and the return of the boat shoe trend to interviews with costume designers for hit shows like Nobody Wants This and The Penguin. When she’s not at work, Hanna can probably be found listening to pop music, talking to her dog, and gossiping with her best friends. For more of Hanna’s perfect opinions on pop culture, you can follow her on Instagram and X.