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Aspirational Attire

BY The Editors | April 22, 2019 | Feature Features

For Skippy Mesirow, dressing up is a sign of respect.

Skippy Mesirow is aware that his sartorial choices draw attention, but that’s on purpose. “A lot of people look at my aesthetic and the way I dress and carry myself, and get the impression that I am a nonworking rich kid, and it’s quite the opposite,” he says. He credits this to his bootstrapping grandparents, with whom he grew up. “They were always very stylish, and they taught me that the way you dress is a sign of respect for the person across from you. You also dress for the job you want—it’s aspirational.” Mesirow is a property manager and entrepreneur, but the job he wants most now is a seat on Aspen City Council.* Regardless of the outcome, he’ll keep dressing up, sourcing inspiration from his travels—he’s been to 43 countries—to create a style he calls “mix and match. I relish the challenge of looking like I spent a lot, when sometimes I didn’t.”

* Mesirow was elected to Aspen City Council in a March election, after this article was published in Aspen Magazine.


“A tux is a staple. I have more tuxes than actual suits, and like to wear them as separates.” $499, Suit Supply,

“I don’t trust anyone with my hair besides Ana BelĂ©n at Salon Tullio.” Salon Tullio, 525 E. Cooper, Ste. 207,

“I love accessories. I get a lot of them during travels. These necklaces are from South Africa, and the ring from Morocco. That makes them truly unique.”

“You can’t go wrong by pairing tux pants with anything, like a T-shirt, to dress it up.” $199, Bonobos,

“I like 3DM Lifestyle for shoes. They’re superstylish and handmade in small batches in India.” Black wingtips, $160,

Photography Courtesy Of: