Gentleman Scholar

The Perfect Suit, Hat, and Drink for Derby Day

Seersucker? Sure! A trilby? True! But you may skip the julep if you like.

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I am hosting a Kentucky Derby party at my apartment, and I’m trying to plan a cocktail list that goes beyond the mint julep. (I haven’t been able to touch mint since drinking nothing but juleps last year.) I try to celebrate as much in the spirit of Hunter S. as possible, so whatever you can suggest that is decadent and/or depraved would be most welcome. Also, clothing: Seersucker? Hats?

Cambridge, Mass.

Troy Patterson.
Troy Patterson.

Photo by Christina Paige

Thank you for your email, Matthew. Would you mind if, starting to answer it, I adjust my posture to address people whose knowledge of horse racing derives solely from an in-flight screening of Seabiscuit?

The Kentucky Derby, America’s most prominent thoroughbred race, will be run this coming Saturday at Churchill Downs in Louisville. Post time: 6:24 p.m. Turf authorities tell us that California Chrome is the overwhelming favorite. Meanwhile, we hunch bettors find ourselves confounded that no horse in the field (which will be finalized Wednesday at 5 p.m.) has a transcendentally awesome name. This year, the nomenclatural heights are modest: Vicar’s in Trouble, Commanding Curve, Big Bazinga. (For the record the most gentlemanly quinella finish in Derby history came in 1965 when Lucky Debonair held off Dapper Dan to win by a neck.)

The iconic quaff of the Derby is indeed the julep. Given Matthew’s mint fatigue, I won’t linger on the fine points of julepology, other than to endorse Virginia Gentleman as perfectly adequate bourbon for this occasion: The price is nice, and the fact of its extra-Kentuckian origins makes it a good conversation starter. Just be aware that some misguided natives of the Bluegrass State, rubbed in the face with the truth that their home has no exclusive claim on the name bourbon, will want to continue that conversation outside.

Despite the sport of it, despite the $2 million purse and the sweetness of the winner’s stud-farm future, this event is foremost a party and pageant. I’m glad that in this understanding you’re seeing eye-to-glazed-eye with Louisville native Hunter S. Thompson who, preparing to report “The Kentucky Derby Is Decadent and Depraved” in 1970, told his editor, “The story, as I see it, is mainly in the vicious-drunk Southern bourbon horseshit mentality that surrounds the Derby.” Dr. Thompson’s narrative rewards close study, yet it must be said that, at this late date, the story’s reputation exceeds its power. Oh, sure, because it marked the advent of the gonzo voice, it remains a milestone, a touchstone, a kidney stone irritating the urethra that is “objective journalism,” but it is hardly a keystone text of the author’s heyday. For voice experiments more compelling than this one, page through the published collections of Thompson’s letters. For evidence that his Derby piece, going on too much about rowdy atmosphere and rancid brain chemistry, has been a bad influence, try sifting through the slush pile at Vice.

Still, the piece ranks as a classic, and looking to it for classic cocktail ideas, we need only check the second paragraph, where Thompson, fresh off an airplane, orders a margarita on the rocks. I’d like to suggest, Matthew, that you add a margarita to your drinks list, and I’d like to suppose that if you were to spice this margarita up—by adding squirts of Sriracha or dashes of Tabasco to your shaker, or by infusing your tequila with jalapeño—you could thereby problematize issues of “traditional” “manliness” while also paying peppery homage to Thompson’s key prop in the story, a spray can of Mace.

For a more traditional Louisville drink, I suggest the Seelbach Cocktail, invented at the Seelbach Hotel in 1917. The original looks something like this: Take 1 ounce bourbon, ½ ounce Cointreau, 7 dashes Angostura bitters, and 7 dashes Peychaud’s bitters and stir them well with ice. Strain the mix into a champagne glass, top things off with sparkling wine, garnish with an orange twist. Now, there is a legend that the Seelbach cocktail, like Silly Putty and LSD, came about by accident, that it was created when a bartender “used a customer’s Manhattan to catch the overflow from a popped champagne bottle.” The excessive richness of an original-recipe Seelbach lends some credence to the tale; I’d like to suppose that it tastes exactly as a Silly Putty egg does to the synesthesiac tongue of someone tripping on LSD. Better bartenders know to cut the volume of bitters roughly in half.

Like any cocktail finished with a pour of sparkling wine, the Seelbach will go right to one’s head, so Matthew ought to present his guests with copious quantities of finger food. Any kind of ham-and-biscuit situation would be appropriate. Further, I earnestly recommend that he go to KFC the day before and pick up some buckets of legs to serve cold. (For the record, the most famous Kentucky snack is the hot brown, but the requisite Mornay sauce makes for messy party food and anyway the phrase “hot brown” does not necessarily settle the stomach.)

Seersucker is worthy of any man’s Derby Day consideration. Are you worried that the first Saturday in May is too early in the spring to wear this marvelous fabric? Guess what: The climate is changing, and the weather has gotten permanently weird, and I am issuing a drive-by decree: You may wear seersucker on any day it is warm enough that you won’t look like a total fool wearing seersucker. All the old rules about what one may or may not wear before Memorial Day or whatever must be destroyed. I will be building a bonfire to burn all the old rulebooks as soon as someone buys me a carbon offset.

But that’s just a general principle. In fact, the Derby Day forecast for Matthew’s Cambridge, Mass., calls for a high of 68 degrees, and he might be better off venturing to the J. Press on Mt. Auburn Street to pick up some madras, a fabric strongly associated with the Derby since the year of Lucky Debonair’s win, when the infield at Churchill Downs, formerly a place for the common man to picnic placidly, began assuming the character of a spring-break bacchanal.

And hats? A gentleman oughtn’t be wearing his hat inside, but I’ll allow Matthew a bit of latitude here, precisely because of his latitude. Any Derby party held north of Cincinnati is properly understood as an homage to the idea of the Derby; it is somewhat permissible to wear a hat inside at such a party because what the guests are up to is, fundamentally, cosplay. Try a straw trilby.