I'm from Baltimore, so I'm pretty familiar with the Triple Crown. It's funny, the Kentucky Derby and the Preakness seem to be two very different animals. For example, when my friends used to go to the Preakness, I don't think they put much thought into their outfits- it was more about bringing in coolers of cheap beer.
Anyway, this is what I would wear to the Derby. I'd probably stash a pair of flats in my purse as well- I'm sure those stands are not heel friendly!
You can check out the rest of the Derby inspired posts at Long Distance Loving!