Talking with A snazzy fashion coach for men


Name: Evan Wolkenstein
Age: 40
City: San Francisco
Position: Teacher, Style for Dorks owner and “chief fashionisto”


J.: You are the director of experiential learning and Jewish studies at the Jewish Community High School of the Bay in San Francisco. How long have you taught there and what subjects do you teach?

Evan Wolkenstein: This was my ninth year at JCHS. I teach Tanach [Bible], but I also coach student council and run holidays and assemblies.

Evan Wolkenstein

J.: You also own Style for Dorks, where you promote fashion and style ideas. How did you get interested in fashion?

EW: I had always been curious about it, but as an outsider, wondering how these mysterious rules worked and that certain people seemed to know how everything operated, especially when I was a teenager. I didn’t feel equipped to understand that style could be a form of expression, except I knew how to put a costume together.

I created a hippie persona and wore a lot of African dashikis, but the only way I knew how to play it was to go with a subculture.  I didn’t know it could be part of your daily life. At JCHS, I met [fellow teacher] Iggy [Igaël Gurin-Malous], who’s a tastemaker and master stylist of sorts, and started taking tips from him. He offered a constructive critique but never made me feel silly, which is exactly how a good teacher should be.

J.: Why did you decide to start a business doing this?

EW: Though my interest in style has been going on for the past six years, I launched last fall. My girlfriend, [food blogger] Gabi [Moskowitz], noticed that my passion for education is probably matched only by my passion for ties. She said, “People want support and guidance from someone they can trust. You can offer that,” and I loved the idea. When I helped a childhood friend discover his own style, I put it on a blog, and the next client to come to me was someone I didn’t know, and that’s how it started.

J.: Usually, men’s fashion is considered a gay man’s domain.

EW: If someone assumes I’m gay because I’m such a great dresser, my response is that I’m honored, but no. I’m all for straight men not saying, “I’m a dude and I don’t care about such things,” but rather, “We want to look great, too.”

J.: Who is your style or fashion icon?

EW: I have four. While I do not appreciate his relationship with women, [“Mad Men” character] Don Draper is brilliant. His look is simple and well-fitting and classic. He’s perfect. The second is Thom Browne, who both designs for his own label and for the Black Fleece label with Brooks Brothers. Brooks Brothers is stodgy old bankers’ clothes, but Black Fleece draws from vintage styles but with a bold, edgy aesthetic. The third is the West Coast heritage hipster thing. Last is my grandfather. He had these photos of himself as a dapper old man around the house, which probably first planted the idea, that that’s what a gentleman does: He puts on good gear when he goes out.

J.: If a man is on a budget, what changes can he make to improve his look?

EW: Clothes have to fit properly. Most men think that what’s off the rack is good to go, but they should take all their shirts to a tailor and make sure the seams are hitting their shoulders. Pants should be tailored properly so they’re not dragging. The second thing is a nice pair of shoes. Invest in a proper pair or something trendy that inspires you, as shoes are often the first thing a woman notices.

Third, if your ties are all shiny silk from a department store, it’s time to give them to someone and get three or four really beautiful ties. Cotton, knit and skinny ones are great. Don’t wear them only at weddings. Wear them when you go out to eat, wear them with your tailored shirt and shoes, and you’ll see how people start to notice.

“Talking with …” focuses on local Jews who are doing things we find interesting. Send suggestions to [email protected]

Alix Wall
Alix Wall

Alix Wall is a contributing editor to J. She is also the founder of the Illuminoshi: The Not-So-Secret Society of Bay Area Jewish Food Professionals and is writer/producer of a documentary-in-progress called "The Lonely Child."