Mad Hatters: Kentucky Derby Hats

May 4, 2010 19 Comments »

kentucky derby hat
The hat lady…

Where am I? From a fashion perspective, it looks like Park Ave., but there are no sky scrapers. A vendor walks by with 3 dozen mint juleps in his ‘Ice Box’ crate; I smell an odor of horses and cigars. For one brief day, this town is the queen of the fashion world and the King of the Sports world – ‘Mission Impazible’ achieved. This can only be the Kentucky Derby, one of the greatest sporting events of all times;  where Devil Wears Prada meets ‘Devil May Care’.

Kentucky Derby Culture

One of the most fascinating things about the Kentucky Derby isn’t the race itself – but the culture of the Derby. It’s one of the only sporting events in the world in which you put on your best clothes to be a spectator. Think about it, do you see men in football stadiums wearing suits and hats? No. More than likely the only hat they have on their head is the kind that holds two cans of beer and a big straw or one that looks like a cheese wedge.

kentucky derby hats
A typical Kentucky Derby couple

Kentucky Derby Hat Variety

Churchill Downs is filled with fashionable hats, shoes, and dresses. The women are dressed as if they are attending a royal wedding or a ‘Nobel’s Promise’. The men are also dressed in hats and summer suits. When you put those well-dressed men in colorful sear-sucker suits together with the women in wide brimmed hats and 4 inch stilettos, you have the perfect Kentucky Derby couple. Even Michael Kors would be impressed.

The hats came in all shapes and sizes, all colors, and some even showed ‘Conveyance’ of the person’s love for horses. There were flowers, netting, ribbons, bows, and BIG bows. In my whole life I had never seen so many spectacular hats. Hat prices ranged from thousands of dollars to a handmade craft project (like my own glue gunned hat). An average hat cost around $300 in Kentucky and they all promptly went on a half price ‘Super Saver’ sale the day after the Derby.

Get updates and watch the Kentucky Derby Live

Life in the Churchill Downs Stands

All afternoon refined spectators in the stands drink mint juleps, and read the racing programs trying to figure out who will be the ‘Stately Victor’ of the big race. Friends gather and talk between races, and eat their boxed lunches in their boxed seats.

However life in the stands and life in the infield (the center of the track) is like comparing an ’American Lion’ to ‘Dean’s Kitten’ – it is an exercise in contrasts. The infield is where the sloppy, less refined partying happens. The tickets are cheaper and so are the clothes. The stands also have their share of partying, but in a sophisticated manner…until it hits 3PM. Then those refined spectators turn into ‘Homeboy Kris’; rowdy, drunk, and a bit sloppy teetering on 4 inch stilettos!

We arrived at out spectacular box seats in the stands around 11AM amidst very grey skies; we were certainly not ‘Lookin At Lucky’ weather for the day. We came prepared with ponchos and flip flops; still trying to keep our fashion sense by wearing our hats and fancy dresses.

One hour later we found ourselves being pelted with rain and gale force winds. We secured our hats, and dawned our ponchos, but even our rain gear couldn’t stop the miserable weather from getting to us. Hours melted away…and with each hour my hat fell a little more apart. However in this time of sogginess, all I could think about was how Vietnam’s rainy season had prepared me for this; I knew that I would not melt. My hat might melt, but my body wouldn’t!

The Race – Short But Sweet & Muddy

After 7 hrs of battling Mother Nature, it was finally time for race 11 – the reason why we were all here; to see the run for the roses. First, I had to place my bets – should I go with ‘Paddy O’Prada’, ‘Jackson Bend’, ‘Discretely Mine’, or ‘Back Talk’? Of should I put all my money on ‘Line of David’? After all, I have a friend named David. In the end I decided to stick with what I know – travel. I cleverly placed my bet for an international theme and chose ‘Dublin’ to win.

By some ‘Awesome Act’ of God…once we all stood up and sang Old Kentucky Home the sun blasted through the clouds, and rays of light shined down upon Churchill Downs. It was as if NBC had paid for this to happen. Or the big rain clouds were simply negotiating by saying ‘Make Music For Me’ and we will cooperate.

And they were off….


The crowd came alive jumping up and down as if ‘Sydney’s Candy’ were being thrown into a crowd of children! There were screams, hands waving, jumping, and even some praying.

In the end…my travel bet didn’t pay off. However, my trip to the derby did pay off big – mainly in the form of photography.

kentucky derby hats
Me and my hat…

*if you haven’t figured it out by now – the bolded names are the 20 horses that ran in the Kentucky Derby!

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