Looks like my new Esquire Magazine subscription at 55 cents an issue is paying off with the following advice for dressing for a Kentucky Derby Party:
The Suit: A Seersucker One
They used to say that only rich men could afford to wear such a cheap fabric, but, seriously, seersucker may never have been this affordable. You can find a full Haspel suit not unlike Gregory Peck's in To Kill a Mockingbird at your local Macy's or Nordstrom, or shop online for a similar option by J. Crew. Even a new jacket is guaranteed to wrinkle, and that's a good thing.
The Shirt: A Clean One
Because nothing looks better with a seersucker jacket than a crisp white shirt, and nothing could be worse than your old pastel thing from the last serious Derby party you attended. Better to trust a U.S.-made, family-owned business like Hamilton, which has been manufacturing shirts since 1883 in Houston, Texas, from where this soft pinpoint ($245) can get to you in nary a furlong thanks to Hamilton's made-to-measure program.
The Tie: A Festive One
Perhaps not until Christmas — or her birthday — will you be this encouraged to get your neck in the spirit. And ties don't get much more festively appropriate than those crafted by the belles Emmie Henderson Howard and Reagan Hardy Howell down at Southern Proper in Atlanta. For the Derby, this julep-themed cravate ($75) is about as close as you'll come to a sure thing.
The Belt: A Heavily Sewn One
Needlepoint belts — ideally made by your mother or, more ideal still, by her mother, and preferably without the maiden name Pulitzer — have been a preppy tradition for decades. But there's grandma-quality labor (about 50 hours each) going into belts made by the official collegiate accessory-makers at Smathers & Branson. (As in, get a flask while you're at it.) Show your Wildcat spirit for a weekend with this UK belt ($165), or check smathersandbranson.com for your own alma mater.
The Pants: A Simple Pair
It's the jockeys who have to ride the horse, so leave the chaps, socks, and especially shorts back up North where you came from. What with everything else you've got going on, just stick to the casual basics — something the twenty something designer Allen Stephenson is growing to master at his two-year-old Southern Tide out of Greenville, South Carolina. His Channel Marker II nautical-themed cotton pants ($99.50) feature red and green button stitching to help you remember right from left when, like we said, you've got a lot of flask going on.
The Shoes: A Two-Tone Twist
There's office wing-tip two-tone, and there's Big Bad Voodoo Daddy two-tone, and then there's this: Southern-daddy haberdasher Ben Silver asking legendary Yankee boot maker Alden to craft a special shoe, and you getting a two–tone slip–on treat suitable for sipping bourbon on any veranda. These split-toe Alden tassel loafers ($475) are an exclusive to Silver's lavish, Charleston-based company; order at bensilver.com, and be sure to request their catalog while you're at it.
Allen Edmonds Neumok - Olive Leather
Tip: If technicolor's definitely not your thing — and may never be — olive green leather is a strong entry point. Especially when it's paired with the blue laces that come with these, but can be easily replaced if it throws your conservatism off too much.
Unlined lace-up leather wingtip ($260) by Allen Edmonds, allenedmonds.com.