Not only is it tradition to wear a hat to the Kentucky Derby, legend also has it that it brings good luck. The Run for the Roses occurs annually on the first Saturday in May at Churchill Downs in Louisville. Ladies and gents dress to the nines and root for their favorite thoroughbred in the race of the year, known to many as the greatest two minutes in sports. With such a huge claim to fame, it’s no wonder the Kentucky Derby boasts the most glamorous and artfully crafted hats, making this the most fashionable sporting event of the season.
My Fair Lady
Channel the rich and famous in an extravagantly sculpted black-and-white hat, reminiscent of the horse-racing scene in “My Fair Lady.” Most of these hats were overly large, asymmetrically placed on the head and embellished with feathers, lace, large bows, ruffles or tulle veils.
In honor of the red carpet festivities, Hollywood’s elite grace the Kentucky Derby styled in wide-brimmed “Southern Belle” hats and large black sunglasses. While the staple large brim comes in a range of colors, celebrities gravitate toward choosing a designer original to complement their entire outfit.
The Garden Party
There will be sun at the track, and much as you would for a spring day spent at a garden party, opt for an upturned, structured straw hat or large-brim sun hat with silk flower appliques. From peonies and roses to dinner-plate dahlias, a formal sun hat with floral embellishment is always in style.
The British may have made fascinators a household name, but American women are catching on to this head-gear craze. While a fascinator is more of an elaborate headpiece, much smaller in size than a hat, usually clipped, pinned or set on a headband, it is still considered formal for its decoration. Often incorporating feathers and structured designs, a fascinator can be placed on a base so it seems to be a miniature hat.
The Vintage Cloche
The vintage cloche of the 1920s has been reinvented for summer’s fashionable sporting event. Made of straw, sisal and sometimes fancy lace, the cloche is a form-fitting, bell-shaped hat, simple in style but timeless in fashion.
Men of Ascot
While the fellas stake claim to being the bigger gamblers, many take little risk in head wear, playing it safe in preppy straw boaters or Panama hats. Some get a little gangster in a classic feathered fedora.
Because the Kentucky Derby festivities include a parade of hats, creating your own cleverly crafted piece of head fashion is encouraged. Hats have been made out of the most bizarre materials, such as a deck of cards, vegetables and plastic pink flamingos. Some even incorporate miniature horse figurines into their style. Anything goes on the hat – there is always a winner for the most unique design.