There are few occasions where one can sport a big silly hat with impunity. Across the pond, creative headwear is part of British party culture; Americans really have only one day and that day is coming up.

Newly launched Boulder Lifestyle Magazine is hosting the Kentucky Derby party this year at Goldbranch Estates in Niwot, supporting TRU Care Hospice and featuring live music, mint julips, fabulous food and everything else you’d expect from a top-notch event. In addition, the two ladies with the most fanciful and fantastic hats will win a $500 Todd Reed gift certificate and a Closet Consultation by yours truly. Buy your tickets here! As I’ll be nominating the best hats in attendance, it’s only fair to provide a little guidance.

GO BIG- Certainly when you think of the Derby, you think of the dramatic- sweeping brims, oversized flowers, massive feathers, ribbons, sequins, fruit (well, maybe not fruit) & fun. The traditional Derby hat (pictured) is a no-holds-barred head-wrapping extravaganza and the quickest way to get noticed and nominated.

GO SMALL– If spending 4 hours in a huge hat isn’t your cup of tea, small and sculptural is another great option. I spent much of last year’s Derby negotiating my huge hat with a drunk crowd so this year I’ve opted for a more modest silhouette.

GO SILLY– Humor is always a hit, though going this route (most likely) requires some DIY touches from your local toy or crafts store. The internet is ripe with inspiration: from literal to political, a funny hat is hard to beat.