The annual Kentucky Derby is more than a horse race and a polo match, it’s one of the first opportunities to put on some springtime fashion and be fabulous. Here’s how it used to be done and how it was done in 2016. (Photos courtesy of WWD.com)
The Hat
This—and church, depending on your age and culture—may be the only place you put on a hat. I’m talking about something with a very wide brim and ribbons and flowers and such. That’s the tradition. But this year, the hat du jour was the fascinator. A fascinator slaps tradition in the face with a glove. It’s a teeny tiny hat, in comparison, perched at just the right angle and festooned with ornamentation. In fact, a fascinator isn’t really a hat at all because you fix it in place with the small comb that’s attached to it.
The fascinator may be fabulous but it offers absolutely no protection for your face from the sun, so don’t forget your SPF 30 and some sunglasses. 
The Dress
No LBDs allowed! Think light colors and pastels. And florals! The Derby is the perfect opportunity to put on a dress with biggest (or smallest) floral pattern you can find. It can be a maxi or a mini, it just can’t be black.
21st century re-mix: Many of this year’s dresses were solid in color so as not to compete with elaborate fascinators. A floral dress with an ornate wide-brimmed hat says Southern chic. A floral dress with an ornate fascinator says … something else.
It’s also wise to bring something for the breeze—sweater, blazer, pashmina, etc. It’s only May and it may decide to be on the cooler side the day of the Derby. This year it rained, so a small umbrella wouldn’t be a bad idea either.
The Shoe
Yes, the platform stiletto goes with almost everything. But one thing a stiletto most certainly does not go with is grass. Tradition: After the polo match, the crowd would be invited onto the field to “stomp the divots”—to press the clumps of dirt and grass that were chopped up by polo clubs back down into the ground with their foot. This is part of the fun, of course—but only if you’re wearing cute flats or wedges. Note: Ladies, traditionally you are on grass, not sand, so leave the flip flops in the car, tucked away inside your tote or at home altogether. Flip flops are not Derby-fabulous, thank you.
This, unfortunately, didn’t stop several ladies from tottering precariously on the cobblestone walkways and sinking clumsily into the grass fields in their stilettos—platform and otherwise. And, alas, way too many women walked around gracelessly in Old Navy $3.50 per pair/2 for $6.00 flip flops that may or may not have matched their dress. *Sigh* 
The Accessories
The hat, a tote and some fun costume arm candy (bracelets) have traditionally served as enough adornment for the day. The advent of the fascinator upholds this less-is-more tradition. In fact, depending on how fancy the fascinator was, in many instances, no other beautification was necessary.
So whether you go to the Kentucky Derby in traditional attire or in 21st century re-mixed attire, we can all agree on one thing: It’s the most stylish sporting event around.
