BB Man: What does it mean to dress like a grown-up?
Moskowitz: I'm reminded of the Hardy Amies aphorism, that "a man should look as if he has bought his clothes with intelligence, put them on with care, and then forgotten all about them." Hardly specific. For a more actionable checklist, I'd add a pair of oxfords, a timepiece that predates your birth year, and any manner of clothing that conforms kindly to your silhouette. Like speech: never too loose, never too tight.
BB Man: What's the most important thing to consider when buying a vintage watch?
Moskowitz: You ought to start in your grandfather's closet and see what you can find. Nostalgia trumps logo or brand. But if heirlooms aren't an option, it's worth investing in a classic and servicing the watch yearly. A watch is the only piece of jewelry (other than a wedding band) that a man ever ought to wear, unless he's a diabetic/epileptic and needs a wristband.
BB Man: What's one specific style practice or staple that should make a comeback?
Moskowitz: Hand-signed thank-you notes. Too few men ever go to the trouble of properly expressing thanks with a pen.
BB Man: Who was your hero (or style icon) when you were a kid?
Moskowitz: I always gravitated towards Salvador Dali; the photo of him strolling around Paris with a pair of anteaters (in lieu of poodles) on-leash. It always struck me as a more lyrical substitute for the middle finger.
BB Man: What's one skill should every grown man should have?
Moskowitz: Cursive writing. You never know when you're going to need to stipend your income by tattooing baby names or biblical verses on people’s necks.
BB Man: What article of clothing should every man own?
Moskowitz: Just find a decent tailor. Nobody needs a 72-piece wardrobe hand-stitched by Gieves & Hawkes. But you need a trusted pair of eyes and hands to ensure that what we do buy fits as it rightfully should.
BB Man: What article of clothing should a man never wear?
Moskowitz: Shorts. There ought to be a stiff penalty levied for wearing cutoffs anywhere in the Lower 48, with three exceptions: the beach, the gym, and the tennis court.
Read our entire Birchbox Man Grown-Up Interview series here.