The torture of finding my Kentucky Derby Hat

With less than one month before the 2012 Kentucky Derby, I answered the phone at Sports Traveler last week to hear this on the other line:

“Um, I’m attending the Kentucky Derby with your company and um… I have a silly question… What should I wear? I mean, I need a hat, but I don’t know where to begin to figure this out. No stores sell hats like that around here. Can you help me!?!”

Oh sister, I hear you. I live in Chicago and the only hats that they sell here seem to be stocking hats for winter!

When I went to my first Derby I was so excited - that was until I started worrying about what I was going to wear. The panic first started when I viewed this website:


  • These women were dressed by professionals and are wearing custom designed, i.e. really expensive Derby hats.
  • They will be spending their entire day at the track sitting indoors and/or have no concept of temperature.
  • They only had to walk 5 feet wearing those shoes.

Synopsis: I have no chance of ever attaining this look.


  • I have to walk really far from the shuttle/parking lot to the track.
  • My seat is outdoors and it may be windy, rainy, cold, hot, or all of these things on Derby Day.
  • I will be at the track for more than 7 hours outdoors and my hair has never looked great for more than 1 hour outdoors.
  • I look funny wearing a hat.
  • Once I get this hat on, there will be no possibility of taking it off, as I will have a weird hat mark across my forehead.


Are you panicked yet? OK, stay calm. Here is my best advice as you shop for your Kentucky Hat and outfit.

  1. Choosing THE HAT: Let's face it. You will probably never wear this hat again, unless it's to a costume party or you attend the Derby again. So, you don't want or need to break the bank on this purchase. If you live outside of Kentucky, your best chance of finding an affordable, Derby-worthy hat will be your urban church lady store. (Yes, I'm serious) I found and fell in love with Lourdes Hats in Chicago. If you want to wait until you get to Louisville, you can try Anne Sawyer located inside the Galt House starting Thursday night. If you go this route, choose a very simple neutral dress (no prints!) that will be easy to match to any color hat. If you are staying in Lexington, try the gift shop at Keeneland Race Track. These hats will be pricey and if you will be flying home, the giant hat box they give you WILL NOT fit in the plane's overhead bin!
  2. No 2-minute shoes. I don’t care how cute you think you will look. The walkways at Churchill downs are old-time bricks. You will be either stumbling, tripping, or limping within minutes if you don’t have steady, comfortable shoes. And please don't be one of those ladies wearing flip-flops and carrying your shoes around!
  3. Prepare for rain! Pack two clear plastic dry cleaner baggies in your purse if there is ANY chance of rain. This saved my hat and outfit from ruin during the rainstorm in 2008.
  4. Bring the little cardigan. Best thing my mother ever told me was to pack a little cardigan to put over me in case I get cold when the sun starts going down.
  5. Don’t forget the Oaks Hat! For Friday’s race, the Kentucky Oaks, ladies wear hats. But, you don’t necessarily have to wear a different hat each day. Try adding flowers or bows to your hat to change the look. (Anne Sawyer's shop does this, too!)


This is my best advice for us ladies. Any other hat shops that you want to let me know about, please comment.


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