In high school in Dallas, I wore khaki shorts and a T-shirt every day. In college in Norman, Oklahoma, I wore khaki shorts and a T-shirt every day. Pleats chopped up the shorts; the solid-color T-shirts billowed. I wore Adidas Supernova running shoes like this: I would by a new pair, put 300 miles on it running, start wearing that pair as my walkaround shoes, and buy a new pair again. I thought the Supernovas were a pretty good look for me. I made exceptions for formal events and rented a tuxedo. Neckties choked; dress shoes pinched. Jeans overheated me, so I owned one pair of Levi’s 550s, which I never wore. I parted my hair down the middle with a comb and left it to its own devices. There are pictures on Facebook. It’s as bad as it sounds.
Slowly, things changed. I lost a bit of weight. Eight girls in my “Shakespeare’s Tragedies” class staged an intervention and took me to a real stylist, who got me using hair product. Combined, that was more women at once than had ever taken an interest in me. I dated a girl who was a Gap aficionado. I dated a girl who appreciated designer denim and took me to my first Filene’s Basement. My pleated khakis wore out. I replaced them with flat-front Gap shorts. I discovered Paper Denim & Cloth and the fact that I have an ass. I bought a white pair of Chuck Taylors. I bought a pair of brown Lucchese boots at the Western Warehouse on Central Expressway in Dallas. They felt good. They felt right. During law school, I clerked for a law firm whose attorneys wore suits every day. I discovered shirt.woot.com.
My tale, ladies and gentlemen, is one of redemption earned slowly. There were setbacks, of course. I tried growing my hair out once. I tried growing a beard. I bought a pair of blocky Steve Maddens. There were a few unfortunate neckties.
The other day, though, I rose early. I pulled on an undershirt and under-trunk. Next came the over-the-calf brown argyle socks to match the brown textured suit pants with chalk-stripe windowpane. The white grid of the pants melted into a crisp white dress shirt, spread collar, chrome-fastened French cuffs. I knotted a richly textured reddish tie with blue-and-white houndstooth and a note of brown that anchored both the suit and the shirt. Brown leather-sole loafers, suit jacket, and a white silk pocket square, casually stuffed, and I was out the door.
In the fall of 2008, I started dapperdistrict.blogspot.com because I kept finding myself thinking about men’s style, reading men’s-style magazines and blogs, and wanting to help my fellow male dressers in Washington.
Whether you’re a schlub or a style maven, Anacostian or Arlingtonian, Hill staffer or hipster, I’m here to help. Style touches everything—grooming, gender politics, feelings, savoir faire, you name it. And most of all, it’s a symbol of respect for yourself and the people around you. I’ll give us a topic every week, and you can go off in the comments. Ask questions there if you have them. Help me find Washington’s stylish men. And because I went first, let’s kick off this discussion with your most embarrassing style moment.