BB Man: How would you describe your personal style? Any overlap with Bob Benson's office prep look?
Wolk: My style is classic. You probably won’t find me wearing anything that doesn't look like it could have been worn in the ‘60s. So in that respect, it is not dissimilar from Bob Benson's. Jeans, T-shirts, sport coats, Sperry's…
BB Man: Which Mad Men character's style do you like most?
Wolk: I most admire Sterling's style. It's classic, but it's also got some funk to it.
BB Man: What's an article of clothing that every man should own in your opinion?
Wolk: Every man should own a good pair of boots.
BB Man: What's an article of clothing a man should never wear?
Wolk: To each his own, but I usually don't wear T-shirts with lots of noise on them. I like to keep it simple.
BB Man: Any tips for being a grown-up in the workplace? Always buy two coffees because you never know when the boss might want one?
Wolk: Bob Benson would most certainly tell you to bring two coffees. But I disagree. You don't want to kiss too much ass, because people get turned off by that. I say hold your own, be respectful, and work hard.
BB Man: Do you remember a moment in your life when you first felt like a true adult?
Wolk: The period of time in my life when my nephew was born. Just knowing there was a generation younger than me out there in the same bloodline—that made me feel like a real adult.
BB Man: Who was your style icon hero when you were a kid?
Wolk: Elvis. I thought he was as cool as it gets. Probably my father's doing as he made me listen to all of his records. And Danny Zuko. I even tried to slick my hair back and do the curl thing. Then I matured and it was Norman Rockwell in middle school.
BB Man: What's one skill every grown man should have?
Wolk: Every man should know how to parallel park.
BB Man: Growing up, your family owned and operated a shoe store. How did that affect the way you buy, wear, and think about footwear?
Wolk: I learned that shoes make an outfit. As soon as I was old enough not to ruin shoes right away, my father never let me out of the house wearing a crummy pair of shoes. He always said that people notice shoes, and they are very telling of someone. I think this is absolutely true. I am a huge shoe nut now. My closet is full of them—most which are still sent to me by my dad from his shop Sundance Shoes, in Michigan.