While the outfits and hats may range from elegant to outlandish, let’s talk about a few practical things, starting with the weather. On the first weekend of May, you may expect any type of weather in Louisville: balmy spring or early winter, sun or downpour, so be prepared and wear layers. Since you cannot carry an umbrella into Churchill’s Downs, you can pack a light poncho into your purse. Purse dimension cannot exceed 12 inches in each direction but that’s plenty to fit a pair of flip-flops or foldable flats. Some parking spots are a fair walk from the grounds and your feet will be grateful for the swap at the end of the day. In case it’s a warm day, think twice about a body-con dress and a shape-wear as it will feel like a hot iron after a while – opt for a loose spring style dress or a breathable suit.