David Moses (center), and vintage fashions sold through his company Winning and Losing

David Moses is the rare fashion creative with nine lives. Moses, who goes by they/them/theirs pronouns, emerged from New York’s downtown scene, a fixture in various underground movements, to codesign some of the city’s more avant-garde labels. Now following a respite from the scene, they are leaving the pressures of the design world’s churn behind to launch Winning and Losing — a vintage clothing company dealing in special items that pass their eye.

Moses, formerly a designer for Vaquera and Gauntlett Cheng (neé Moses Gauntlett Cheng), has long been seen as something of a style auteur. Along with some of their Vaquera codesigners, Moses worked part-time as a buyer for the New York thrift store Beacon’s Closet as a source of steady income. It gave them first access to discarded goods to emerge deep from people’s closets, which they leveraged for access to ironic logo designer bags and miniskirts from the early Aughts. These, along with many other of Moses’ earlier fancies, went on to become nostalgic trends in the mainstream.

Following a break from the fashion world for mental health and personal recovery, Moses accepted that the industry’s cycle was at odds with their own creative cadence.

“It just got too fast for me, making two collections a year doesn’t seem like a lot, but it just got to be too crazy. I think my experience had to do with not being able to cope with that,” Moses said of their decision to step away from design and reevaluate options.

They returned to Beacon’s with a new appreciation for clothes of the past — particularly hand-sewn vintage items, rather than designer castaways. In a short time, Moses amassed an archive of more than 1,000 items — first as a hobby more than a commercial pursuit.

“Being a buyer gave me so much insight into how emotional clothes are. Being face-to-face with people and evaluating their clothes on whether or not to buy it for the store was an incredibly intense process. Clothes are so personal,” Moses said of their enduring attraction to material goods.

In the last two months they have begun slowly introducing items for sale on Winning and Losing’s Instagram page. Moses derived the name from a book they happened upon in high school that read, “Winning and losing, both are confusing,” the title and author of which Moses has long forgotten.

Moses’ vintage finds encapsulate this same intuitive spontaneity. Rare midcentury graphic sweatshirts are posted next to Sixties tinsel shift dresses, Depression-era calico jackets, Edwardian summer linen gowns and Seventies debutante tulle frocks. The only similarity they share is Moses’ keen eye for unique, wearable vintage pieces that exude personal details and nuanced history.

Their company is still in nascent stages, but has already gathered interest from the same kind of fashion plates that had enjoyed Moses’ contemporary designs.

In selling direct online, Winning and Losing is a member of a community of dealers that have fashioned themselves as Instagram vintage connoisseurs. Their social media feeds, with each post advertising a new item for sale as well as its story and provenance, also function as fashion history archives — creating a sense of trust with shoppers who have an appreciation for old clothes. Moses also lists vintage wares on Etsy, but has plans to launch their own e-commerce site once the company accumulates a big enough following.

“Now more than ever, extending the life of clothes is really important,” Moses added of vintage’s one-off charm and environmental factor. “I have been mending a lot and am really interested in extending the life of clothes as long as possible. I’m really attracted to super-thrashed clothing or super-old denim that’s messed up and putting work into it. To buy really tattered pieces, fix them and resell them,” Moses said.

Moses next intends to bring Winning and Losing on the road for premium vintage shows like Brimfield, when it reopens following the coronavirus crisis. They will also begin loaning clothes and objets d’art to set designers and costumers.

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