Dressing for the Kentucky Derby

Shopping for a hat, either for Kentucky Oaks and/or Kentucky Derby, is a tradition for many Louisville ladies.
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First, a little Derby history: The race, founded by Colonel M. Lewis Clark Jr., was designed to be pleasant yet opulent, an event to rival European horse races. So, even early on a trip to Churchill Downs on Derby Day included luxury, complete with stunning outfits. Interested in more Derby history? Check out these Kentucky Derby Fun Facts.

Kentucky Derby Dresses

In the late 19th and early 20th century, Kentucky Derby dresses were long enough to cover the ankles of well-to-do ladies and most were probably accented with a hat and gloves. Of course, expectations on what a woman should wear changed in the 20th century. Suits became more popular than dresses. By the 1960s women were still dressing up, but the hats became wilder and the importance of gloves was on the wane. Skirts became shorter and patterns were louder.

Today, a hat is still fashionable and they tend to become more ornate (and expensive) with every year that passes. It is common to see women in sleek dresses or light sundresses, often with short hemlines. It is common to keep your dress silhouette straightforward, allowing the Kentucky Derby hat to take prominence.

Also, as a side note, the first Saturday in May can be hard to predict as far as weather goes. If possible, think about layers. Derby Day has taken place in the midst of snowflakes and under blazing summertime sun. Be prepared!

Kentucky Derby Hats

Why do people wear fancy hats to the Kentucky Derby? Because it is fun! And, maybe even more important when you are at the track, wearing a hat to Derby Day is thought to be good luck. Although the elegant hats were initially for ladies, men are part of the tradition now too. Stylish wide-brimmed hats are often donned by the women, a nod to the Southern flair of the Kentucky Derby. Not willing to splurge on a hat you'll most likely wear once or twice? No problem, you can make a festive hat at home too!

Should I Focus on the Hat or Dress?

Well, this depends on who you ask. One school of thought is to decide on your dress first, because then you can create or purchase a Kentucky Derby hat to match your outfit. Of course, there is another camp who feel the hat should be selected first as it is the crown jewel of most Derby Day outfits. Whatever you decide, below are a few things to consider:

  • Crazy hats pair well with simple dresses.
  • With a wild outfit, choose a compatible hat.
  • Wear sexy heels if you'd like, but pack an alternate pair of flats. Derby Day is long!

Of course, all these tips work for Kentucky Oaks too. Just remember, the official color for Oaks Day is pink. The more pink, the better.