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Dressing for the Derby

By Heidi Potter

While some Derbygoers might not know what horses are running in the Derby, they definitely know what they will be wearing to the Derby. One could argue that the Kentucky Derby is as much about the fashion and style as it is about the horses. No other event in Louisville compares with the level of anticipation, preparation and excitement surrounding the city at Derby Time.

Derby is so much more than a two-minute horse race on the first Saturday in May. It is a lifestyle that locals embrace every spring — a week-long buffet of events, parties, gatherings and horse watching – now stretching to two weeks as the social calendar grows. The famous Derby Week days leading up the Derby include early-morning breakfasts at the backside of the track, a steamboat race, the Derby parade and days at the races. Friends from near and far gather together. The common denominator of these events is fashion. It takes experience and finesse to plan outfits for Derby Week.

Local retailers build their inventory starting in the winter to prepare for this fashion frenzy. In the midst of a bitter blizzard, women can be found trying on bright, lightweight dresses, as men peruse the newest pink ties and white bucks. Ideas take root and Derby outfits are envisioned through the dark and dreary Kentucky winter. Derby is the light at the end of the frozen tunnel.

There are many understood rules of fashion at the Derby -- from the styles of hats, to the colors of outfits, to the shoes. The general expectation dictates creating a look that’s completely together, yet effortlessly so.


Hats are the signature piece of the Derby ensemble. They are first and foremost on Derby guests’ minds. Photographs from the earliest Runs of the Roses show guests wearing hats, and the tradition has continued. For ladies, a hat is de rigueur, and if not a classic hat, some sort of headpiece such as a fascinator, a headband or even fresh flowers needs to be present. Men also have embraced the modern hat trend, wearing straw hats, fedoras, even baseball hats with their favorite horse’s insignia on it.

Oftentimes, hats are purchased and designed before a Derby dress is purchased. Similar to the chicken-and-egg debate, it’s hard to decide which comes first: the hat or the dress.

Hats are an exemplary way to express one’s creativity. Many guests design their own hat, embellishing with feathers, ribbon and elements that establish a signature style. Others choose to buy off the rack or have their hat custom-made by a milliner.

The Colors of Derby

For both men and women, color is key to the day. Like the hat, there is an unspoken code that Derby guests dress colorfully. For Louisvillians, this is their chance to arise out of the winter doldrums. Gone are the drab blacks, browns and muddy neutrals of winter clothes. Churchill Downs is awash with spring hues. Though it has snowed on Derby Day and been frightfully cold, guests still don bright and cheery outerwear. Pink is the color of choice on both men and women, particularly on Oaks Day as a “Pink Out” day, honoring Breast and Ovarian Cancer Survivors. Look for pink on hats, ties, suits, shoes and accessories on men and women alike this day.

Classic Men’s Uniform

The classic men’s look at the Derby is the “Southern Gentleman”: a seersucker suit, white bucks and a bow tie. For the gentleman who does not wear this, a suit or a sports coat and slacks are always a handsome option. Men accessorize with vibrant long ties or bow ties, pocket squares, colorful socks and hats — usually these touches boast an equine theme, with horse- and jockey-inspired wares.

Classic Women’s Uniform

Traditionally, women wear a dress or a chic skirt and top ensemble. However, pantsuits and even suiting with stylish shorts are appropriate and have been making the fashion pictures recently. Dresses rule the day by far, with brilliant color and detail always present. Accessories include the mandatory hat, beautiful shoes, fine jewelry and a properly-sized handbag.


While the ticket prices differ at each viewing venue at Churchill Downs, the attitude toward dressing does not vary much. With the exception of the Infield, everyone dresses up for Derby. Whether guests are sitting on a bench in the paddock, or have a personal waiter at Millionaire’s Row, all guests dress up for the day. Even the infield has its share of fashion, ranging from costumes, to full formal dresses, to shorts. However, for the most part, infield guests wear clothing that they do not mind destroying.


Spring has sprung all over Churchill Downs on the first Saturday in May. Rain often threatens during Derby week, and meteorologists issue their forecasts well in advance as everyone prays for clear skies on Oaks and Derby days. Derby guests are undeterred by weather, and for years have regularly fought extreme conditions dressed beautifully. Savvy ladies invest in clear ponchos to properly show their outfits. Every seasoned Derby goer has ruined a garment and/or a pair of shoes in the rain and the muck. Each rainy year, the tide of rain boots and flip flops accompanied with lovely outfits come streaming into Churchill Downs, often with a good pair of shoes in a bag nearby to be worn inside. The infield attendees have learned to embrace the weather, wearing their mud as a badge of honor.


Women are slaves to fashion, especially when it comes to shoes, which are such an integral part of the ensemble that beauty cannot be sacrificed for mere comfort. After eight-plus hours of walking, most ladies crumble in the face of horrible blisters, cramped toes and general pain. All over the track, women apply Band-Aids, rest their feet, or resort to going barefoot. Many a beautiful shoe has been tossed to the back of the closet after a long day at the track, never to be worn again, or at least not until next year’s Derby.