Step 1: Get Yourself A Nice Hat
You're not dressed for the Derby until you're wearing a hat at least three feet in diameter. Tinsley Mortimer has never been one for great fashion risks, so her derby hat (pictured left) is perfect: the requisite size, but still relatively demure in color, it will go well with the no doubt pink dress she will pair it with tomorrow.
When shopping for your own Derby hat, head down to SoHo to milliner James Coviello's Orchard Street shop. Coviello's hats are bursting with feathers, flowers, and other embellishments that would make anyone the talk of Millionaire's Row.
Another option is Barbara Feinman Millinery in the East Village. Feinman hats are all made using a 100 year old sewing machine, which just might imbue the hats with a touch of Gilded Era Derby Magic.
Just be sure to keep away from this Derby Don't:
Step 2: Prepare Your Kentucky Derby Playlist
Blue Moon Of Kentucky (Patsy Cline)
Fugue For Tinhorns (from Guys And Dolls, but.)
Jockey Full Of Bourbon (Tom Waits)
Kentucky Rain (Elvis Presley)
One Mint Julep (Louis Prima)
1812 OVerture (Tchaikovsky)
Kentucky Derby (Chet Atkins)
My Old Kentucky Home (Folk)
Whiskey In My Whiskey (Felico Brothers)
Step 3: Find the perfect Kentucky foods.
Burgoo is a stew made out of random meat, for example venison, squirrel, or opossum. Of course, you can bypass having to hunt squirrels in Washington Square Park and instead opt for pork or chicken. Burgoo, of course, is the official food of Derby Day, and (fun fact), the first rose blanket was awarded to 1932 Derby Winner "Burgoo King". So there you have it.
Because no NYC restaurant in their right minds actually has Burgoo on the menu, you'll have to make it yourself: here's a pretty good recipe.
Of course, fried chicken, while not necessarily authentically-Derby, is much easier to find in New York, the most high brow obviously being Momofuku's Fried Chicken Dinner at Noodle Bar. If you're looking for a more "down home" cuisine, Yelp lists Amy Ruth's in Harlem as being the best fried chicken in New York, and definitely worth the jaunt up to 116th.
And for the truly lazy, you can always inhale a Double Down at any KFC chain in the city.
Step 4: Find the best Mint Julep
The Mint Julep has been the official Derby drink since 1938, when they were available for 75 cents in Souvenir Glasses. Taking a cue from Daisy Buchanan in The Great Gatsby, head over to The Plaza for a perfect Mint Julep. If you're less "Millionaire Row" and more the debauch "Infield",ad to the more affordable Social Bar and Lounge, where you can watch the races while sipping a $6 version of the official drink.
If Mint Julep isn't your thing, try this super easy recipe for Sweet Tea:
1 Part Bourbon, 1 part coke, 1 part Sweet+Sour mix, and 1 part Triple Sec. Mix together and serve over ice with lemon.
Step Five: Place Your Bets
According to the New York Times' expert Steve Davidowitz, the favored horses this year are Awesome Act, Mission Impazible, Lookin At Lucky and Ice Box. So you can follow his advice, or you can do the time honored strategy of choosing a horse purely on how cool his name is.
This year, the clear winner in the awesome name category is Homeboykris, whose family tree is pretty distinguished, you know, for a horse.
Once you choose your horse (and, really, at this point, how can you NOT go with Homeboykris?), head to Chatham Square on the Bowery, or any number of NYC Off-track betting locations.
Bonus: Entertain Yourself
The horse race is only two minutes long, so you best find ways to entertain yourself when it's all over, especially if you spent $400 on a hat for the occasion. You could take this fun internet quiz in which you have to guess what is a horse's name and what is an album title. You could buy a bunch of flowers and weave them into your own blanket of roses. Or you could keep drinking.