Derby hat fashion tips

If I were a betting girl (and, on occasion, I am), my money for this year’s 2013 Kentucky Derby would be on Goldencents, the thoroughbred partly owned by University of Louisville’s head coach, Rick Pitino. After wrapping up his second NCAA men’s basketball national championship, I’d wager he’ll carry his winning streak on through to the Run for the Roses at Churchill Downs on May 4th.

So, now that I’ve determined which horse to bet on, the more important question arises: what to wear?

According to the official Kentucky Derby website, there are a few hard-and-fast rules regarding fashion other than the 139-year tradition of flaunting styles ranging from classic to outrageous. The more refined attire is generally found in the paddock and clubhouse, while out in the infield, anything goes. In either arena, the most enduring tradition is big hats for women and bright colors for men.

From its inception, the Derby has always been about the influence of European fashion. When it comes to trendsetting, who could forget the buzz created by HRH Princess Beatrice’s big, pink bow hat, which sold for $130,000+ on eBay?

For the event famously known as “The Greatest Two Minutes in Sports,” hat-wearers dare to be equally outlandish. In determining your Derby day headwear, here’s the lowdown for topping off your 2013 party attire:

SIZE: Since wearing a hat to the Derby is believed to bring good luck, perhaps the mindset that follows is: the bigger the hat, the better the luck. At Churchill Downs, large-brim hats not only provide sun protection, but also embody the southern belle influence. With Wisconsinites still waiting for spring to arrive (and with no worries of sun overexposure), going grandiose with a hat might brighten up spirits, if not the weather. A wide, floppy brim is best for being dramatic without looking, or feeling, too heavy.

SHAPE: This is up for grabs. Anything really does go here, from hats in the shape of Churchill Downs, to horseheads, to pillboxes, to the most whimsical creations. Even a Cheesehead wears well for Derby festivities.

COLOR: Red—for the roses, the official Kentucky Derby flower—is always a perfect color choice, as is the classic look of black & white. Bright colors and bold or pastel shades stand out and evoke the excitement of the potential “pot of gold,” if you and your horse’s luck pays off.

EMBELLISHMENTS: Flowers, feathers, ribbons, bows and anything equestrian find their way as adornments on Derby hats, often times all on the same hat! Usually, an overall theme for your Derby Day ties your hat, outfit, and colors together. In the craziness that carries the day, abandonment is encouraged. If you’ve ever wanted to free yourself and mix things up, a Kentucky Derby Day party is your excuse.

If you’re highbrow, or fortunate enough to shop Chicago, among several exceptional boutiques is the Gold Coast Couture, with notable designers, among them Philip Treacy, who created the celebrated Beatrice hat.

For the Third Coast locals here in Milwaukee, Lisa Hatch Millinery, featured last year at The Iron Horse Hotel’s “Talk Derby to Me” event — THE place to be for the best Derby party and mint juleps in town — has beautiful and original designs.

The Brass Rooster, a men’s custom hat shop, will be at the Iron Horse this year for their third annual party on race day, Saturday, May 4th at 3:00pm—the race begins promptly at 5:25pm. The Iron Horse will award the “Best Hat” a $50 bar tab prize.

Men are not excluded from Kentucky Derby costuming. In addition to hats, men can swagger with style in seersucker or linen suits (think polo tourneys or Gatsby), gingham shirts, or a preppy, navy blazer with khakis. Even tuxedos, from classic to flaming colors, make for festive and special-occasion wear at the track or Derby party. Since neckwear is customary for gentlemen, a flamboyant traditional or bow tie adds pizzazz to their overall Derby party appearance. Regarding this year’s footwear, there’s no better choice than Gucci’s famous horsebit loafer, which celebrated its 60th anniversary last month.

The Kentucky Derby keeps making its way onto many people’s bucket list. If you can’t be there to experience it firsthand, there’s no reason not to experience the tradition of the Triple Crown by hosting a Derby party of your own, or attending a Derby event out.

What’s your Derby style?