Q: I'm new to the official MB philosophy (though not my own unofficial one), having only recently discovered this site. I could use your insight into a matter I face. I plan to attend the Kentucky Derby this year. What is the best way to dress for this occasion? Can I go the MB Gregory Peck route and wear a seersucker suit or has this look be taken over by too many toolbags in recent years? Also, is the boaters straw hat TTH or just too barber shop quartet?
A: Jon, welcome aboard. "Classic with a twist" is our general aesthetic philosophy, and in the case of something like a 135 year-old horse race in a slave state, a fair amount of middle-finger-fully-extended irreverence is definitely in order. Go for the seersucker, but make sure it's excessively rumpled, like you weren't sure there was a race that day and had to pull it out of the back of your closet last-minute. Instead of the traditional white bucks, go with the white Chucks. And when you order a mint julep, have the bartender make it a double and hold the mint, sugar, water, and ice.
Regarding the boaters straw hat, wear it only if you're bald or sing a cappella, or both.
(The 135th running of the Kentucky Derby is on Saturday, May 2, 2009.)