Last year I was asked to be a celebrity hat judge for the Virginia Gold Cup and I still can't wrap my head around why anyone would ask for my expertise around hats. Aside from the requisite knit beanies everyone in D.C. seems to have, I own exactly one baseball cap, which is currently shoved under the passenger seat of my car. What's even less fathomable is that I was asked to judge again this year.
When I stepped into the winner's circle with my fellow judges, I was informed I was the only repeat arbitrator. So clearly I'm now qualified to give advice on how to make sure your hat stands head-and-shoulders above the competition.
1. Know your categories
When you're brainstorming ideas for what to wear, it's a good idea to keep the judging categories in mind so you can customize your look. For example, if you're going for most elegant, maybe don't tack a bunch of My Little Pony horses onto your hat - although that could be a winner if you're eyeing the prize for best racing theme. The categories are funniest or most outrageous hat, best children's/teen hat, most glamorous, best racing theme and best men's hat, so plan accordingly.
2. Fall is easier
Gold Cup takes place in spring and fall, but the competition is a lot bigger and more intense in spring. If you're a first timer or just don't want to duke it out with people who treat the hat competition like their own personal Olympics, stick to the fall.
3. Coordinate your outfit
One woman walked away with a ribbon in part because her outfit matched her hat - the presentation of the whole package really set her apart. Although your outfit doesn't have to match your hat exactly, it should at least be complementary.
4. Get the guys in
In Spring, the men's competition is laughably small - in 2016, there was only one entrant. If you're a woman completely bent on winning by any mean's necessary, enlist a man in your life to wear your hat creation and sign him up for the competition. If you're a man, this is your time to shine and bust out the hot glue gun.
5. DIY it
You can buy plenty of super fancy hats, but is it really fun to beat the competition if you know you've won just because you blew a lot of money? It's perfectly acceptable to buy a hat to begin with, but add some personal flourishes and make it uniquely yours. That effort impresses judges and ensures that your hat is different from everyone else's - a huge advantage in the competition.