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Inside the Coolest Upper East Side Atelier

Claire Olshan and her luxe design showcase are ready to break higher ground in New York City

No one ever said building a store from the ground up would be easy—especially in 2010, when Claire Olshan first had the idea for Fivestory. “Oh, honey,” the 30-year-old recalls in a low, conspiratorial tone. “When we signed this lease, there was no Celine, there was no Lanvin, there was no Dolce. After the recession, Madison was such a sad, sad place to be. I wanted to breathe some life into it.”

The boutique’s shoe salon

Olshan leans forward on a plush bench on Fivestory’s ground floor as she speaks, her long, dusky blonde hair falling over her shoulder. Despite the flatlined economy and her lack of retail experience, Olshan—the daughter of a wealthy animal skins importer and a former gallery girl—dreamed of transcending garden-variety luxury. She made it her business to infuse traditional Madison Avenue with some personality by providing a curated selection of cult and couture brands like Off-White and Proenza Schouler. Thanks to her father’s patronage and a go-go attitude (she stuck with the name “Fivestory” despite being forced to settle for two floors after an initial lease fell through), Olshan’s dream prevailed: Amid a flurry of Mylar balloons and pre-Instagram “It girls,” Fivestory opened its doors in 2012.

Ground floor shopping parlor

This year marks the store’s fifth in business, but don’t expect another celebratory bash: Olshan says she now considers such expenditures to be a “waste of money.” In lieu of a party, Olshan is investing in the future. In June, she will unveil two new floors, making room for an atelier, an expanded shoe wall and space for wellness pop-ups. “In the last few years,” she says, “I realized that it has to be all about our clients. I’ve shifted most of my attention from products to people.” Just then, as if to prove her point, Olshan stopped to reassure a customer about the size of a long-backed jacket from her own line, Fivestory New York. 

The past few years have been groundbreaking for Olshan in more ways than one: Last summer she married her longtime boyfriend, financier Michael Olshan. “We had a lot of breakups while I was building this store,” she says. “It was not part of my five-year-plan. . . [but] marriage makes you feel more grown up.” And Fivestory seems to be growing up with her, with a few new stories to prove it.