My parents raised me in defiance of the saying clothes make the man, and as photos from high school and college attest, I may have taken their teachings too close to heart. I forced my academic and musical accomplishments to stand for themselves, unaided by my pyramid-shaped outfits. In almost every teenage photo of me, a skin-tight t-shirt flares into baggy cargo shorts and boot-cut jeans, with stretched-out crew socks bunched around my ankles. When internships forced me to update my wardrobe, I scoured Goodwill for sales on shirts that fit well enough, by which I mean any small or medium that still had most of its buttons. Less money for clothing meant more money for hiking, traveling, and booze.
I eventually learned that clothes do make the man, at least for casual dating and first impressions, and that a professional ensemble legitimizes a freelancer’s prices as much as his portfolio does. To the horror of my anti-appearance past, I now research styles, brands, fits, and combinations. I own a jacket that cost as much as a plane ticket and underwear that didn’t come bundled in shrinkwrap. I pay a tailor to fit shirts to a nine-inch drop. I’ve bought a pair of dress boots custom-made for my feet; the bootfitter measured not just length, but width, foot circumference in three places, and leg width all the way up my calf like stripes on a sock.