I've never been to Kentucky, nor the Kentucky Derby, but I had a great time at the Melbourne Cup in November 2001!
www.vrc.net.au
I really enjoyed seeing everyone all dressed and checking out the other hats, etc. The department store, MYER (kind of like Nordstrom's) sponsors a fashion contest called "MYER Fashions on the Field", where it's like a pagant competition, but for your outfits.