Drinking and Dressing for the Kentucky Derby de Mayo

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You know Frank—he's been writing about menswear, sales, television, new shops, the recession, Lisa Loeb, the Golden Girls and getting blasted for Racked for over two years. Well, we think it's time you got to know him and his quirky-irreverent views on life and fashion even better with his column: Love, Frank. Taking the form of an open letter and always signed with love, Frank will rant about whatever style-related conundrum he encounters in a given week. So buckle your two-toned leather Moschino belts, folks, it's going to be ? Something.

Dear Derby Goers and Watchers; Tequila Fans,

Big weekend, huh? Tomorrow is not only the preppiest day on the calendar—Kentucky Derby Day; it's also Cinco de Mayo. And whether your day centers around the "Most Exciting Two Minutes in Sports" or, well, tacos—you're going to be dressed and you're going to be drinking.

A little background: The Kentucky Derby is the most major horse race and takes place at Churchill Downs in Louisville, Kentucky. The horses, thoroughbred of course, are three years old across the board; the race takes literally two minutes; and it all kicks off a two week festival of horsery. Why it matters to you: Really over the top dresses; the opportunity to wear piping and bow ties and ridiculous hats, and Lilly Pulitzer. Oh, and bourbon.

And, Cinco de Mayo—not actually Mexico's independence day (that's September 16th (another opportunity to eat tacos and dance for margaritas))—is a commemoration of Mexico's unlikely victory over France in a battle in 1862. Essentially, it's Mexican Pride day. Why it matters to you: This is the day you can really get away with your neons, your slut reds, your clashing colors, all those crazy-hued garment-dyed jeans you just bought at the Gap. Also, tequila without judgement.

(One friend of mine, who counts Cinco de Mayo amongst her favorite holidays (and why wouldn't you?), calls it a celebration of the sacred birth of tequila.)

Now, if your day is more centered around the race—may we suggest you toss any true prep inhibitions aside and just go for it. Frankly, that whole WASPy, boozy, Southern look—pearls and pastels; Weejuns and D-ring belts; grosgrain on everything—it never really goes out of style. You can always buy it (J.Press to J.Crew and a million other prep school-approved brands in between); you can always wear it; it's a no brainer.

That said, it's a particularly good season to dress Derby. Dresses and skirts in just about any style are ubiquitous. Bold color is in and very, very available—so you won't wear whatever flamboyantly toned garment you settle on only once. And it's not just color that's happening—preppy is still everywhere. Even Urban Outfitters is on crew. Check their Burkman Bros and Trovata collaborations. Both are very Amherst students on holiday in Mexico circa 1987; Saab not included. There's a reason you can't get your Sperry boat shoes at DSW anymore—everybody wants a pair. Point is, it's a very good time to just go for it.

Vinyard Vines makes it very easy. They are, obviously, the official clothing sponsor of the Kentucky Derby. To commemorate the occasion they created a capsule even more colorful and even more cloyingly, adorably preppy than their usual wares.

I love it. Harlequin and bunting prints, horseshoe- and harness-motif ties, pastel shifts, candy-colored ribbon belts, all the requisite piques and seersuckers (mens and womens!); there's obviously a lot of lavender. It's great—I'm especially taken with a little skirt pieced together from various equestrian-themed ties. Just, you know, leave the fascinators to the Golden Jubilee.

All that said, if your day is more about limes and cilantro, may we suggest rough and tumble basics in eye-piercing colors with, perhaps, a Western flair? Nothing too fancy or delicate—you'll just ruin it when you're ice luging.

Personally, I'm more Cinco than Derby. Plus, when am I not dressed for the Kentucky Derby? Tomorrow, I'll be wearing my Official Cinco de Mayo shirt: A thrift store find. It's a broadcloth oxford from Gap circa 1985 in electric red, yellow, green, and blue tartan plaid. It's frayed and shredding and absolutely amazing.

· Love, Frank [Racked]