Street Style: Tote-ally Chic

Kiefer Roberts carries himself (and his bag) with style.

I photographed this stylish man on the street, only to realize he was the fabulous Kiefer Roberts, one of my friends from high school whom I haven’t seen for 6+ years (!). I was thrilled to see him because he’s a warm, lovely, smart guy. And well-dressed, to boot (pun intended). After catching up, I asked Kiefer a few questions about Boston style, what he listens to, and what blogs he reads.

What are you wearing?

A J.Crew puffer coat, Rugby chinos, Cole Haan desert boots, and an East-West bag by Holly Caldwell, a handbag designer who started locally. My scarf is from a street vendor in SoHo.

Tell me what you think about Boston style.

I think Boston gets a completely bad rap when it comes to style. As a city with so much history, we’re very proud of that and have developed a very particular style and look which can often be seen as stuffy or boring. I think Bostonians would do a bit better with being less judgmental when people try and break out of the typical New England prep style, though, and that way we’d be viewed more positively and be able to be more daring.

Where do you shop and what style blogs do you read?

I enjoy the J.Crew Men’s Shop, and Sault and Uniform on Tremont Street. As for style blogs, I’m obsessed with the snarkiness of New York Magazine’s ‘The Cut.’ I love Fashionista, The GQ Eye, and Por Homme.

What are you listening to?

I’m having a serious moment with Mumford and Sons and I’ve been listening to their live stuff a lot, as well as CSS’s La Liberación and for working out, strictly Avicii and Swedish House Mafia.