Details and community make Sienna Ray’s perfect hats

One time when Natalie Kathleen, the one-woman dynamo behind Sienna Ray, was working on handbags for a summer collection, she was using perforated leathers. She had given all the specs, worked out all the details, and when she opened the bags she expected to see perforated circles in all of the bags. Instead, she saw perforated hexagons. Not knowing what to do, she got on Twitter and told the world, “I love hexagons!

It’s a small anecdote that’s endemic of Kathleen’s style: obsessed with the details and ready to roll with the punches. Sienna Ray, founded on a kitchen counter top when she was working for Vancouver Magazine, started with an eagerness and a kick: Kathleen made a bag, then showed it to an editor of her’s and said it should be featured in the magazine. The editor replied that she should have more than one bag. Kathleen took it to heart and one-upped her, making five different styles and getting them into five stores.  While the bags are all different, they all share Kathleen’s signature lining, a brightly colored feminine design that juts out as soon as one is opened. It’s a bag that shows its personal touch in ways both loud and quiet.

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Kathleen has been an athlete for as long she can remember: before Sienna Ray, before writing at Vancouver, she was both a SCUBA and ski instructor. Since starting Ray, she’s been looking for the chance to incorporate that sporty side into her designs. This called for a new product, and she looked at hats as a “chance to get back to her roots”. These leather hats, which include a startling gold, are meant to invoke athleticism coming from the wearer, as opposed to a team. “I wanted something in between a baseball cap and flat top hat”, she says. This is enforced by the lack of logo: you’d have to ask the wearer where they got that hat if you wanted to know. That’s intentional on Kathleen’s part: she prefers to pique people’s curiosity, to “get that desire for someone to want to know what it is”, she says, rather than push her brand into people’s faces.

While Sienna Ray is clearly her creation, it takes a village to raise a handbag or a hat. Kathleen has worked with both American and Chinese manufacturers, and while she is currently working with American ones, it wasn’t always that way. It took the financial crisis of 2009 to open doors to smaller manufacturers for Sienna, before that they simply weren’t interested in the fifty-bag runs. “Even in New York now, it’s tough, it’s harder to sell in small quantities because it’s expensive”, she says. Once she was in, she was determined to stay in that market by making herself as needed as possible. A strong believer in “pay it forward”, Kathleen as clued in fellow quality small brands — the type that pay on time — to her strong connections.

At the WeWork holiday market, Kathleen plans on expanding on her “business ethic of sharing things” by supported a few other companies, including 41 Winks, a bedding company in which she has helped with branding work, and Red Head Cookies, the cookie brand of a fellow bagmaker who makes treats on the side to support her mother’s retirement. “This is their first big holiday market,” Kathleen notes, “so I told them ‘Hey, I’ll put some cookies on my table!’”

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Photographs by Lauren Kallen.

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