Kentucky Derby Hats: How to Choose Yours (and Wear It to the Preakness)

There is no accessory quite like a Derby hat. For one weekend in May, an entire grandstand agrees that bigger is better, brighter is best, and a little theatrical is exactly right. I love it, and living in Maryland I get to love it twice — because two weeks after Louisville, the party comes home to Baltimore.

A quick word on the tradition

The hats are not a costume; they are the dress code. From the very first run in 1875, the Kentucky Derby was styled as a society event, and elaborate millinery became part of the spectacle — a tradition Churchill Downs still leans into, treating hats as a time-honored Derby signature tied to the day’s old-fashioned elegance. The roses came along the same way: the winner is draped in a garland of more than 400 red roses, which is why the race earned the nickname “the Run for the Roses.”

How to choose a hat that actually flatters you

A great Derby hat photographs beautifully and lets you get through the day. Three things to weigh:

• Brim width to face shape. A wide, sweeping brim balances a longer face and reads classic. A smaller fascinator or a clean boater suits a rounder face and is far easier to manage in a crowd. When in doubt, the brim should be about as wide as your shoulders are — generous, not unwieldy.
• The right anchor. Wind happens. A hat with a sturdy base, hidden combs, or a wrap that sits low on the head will save your afternoon. A fascinator should clip into hair you have actually styled, not slick.
• Color story. Pick up one color from your dress and let the hat amplify it. Pink and green is, of course, my answer — it is the same instinct that drives my preppy spring staples. And do not forget that brim is doing real work as sun protection, which I never take for granted after writing about beating the heat.

Maryland’s hat day: the Preakness

Here is the local secret. You do not have to fly to Kentucky. The Preakness Stakes, the second jewel of the Triple Crown, runs at historic Pimlico Race Course in Baltimore two weeks after the Derby — and the hats are every bit as glorious. Maryland even has its own flower moment: the winner is blanketed in a garland made to look like black-eyed Susans, the state flower, in a tradition the Maryland Jockey Club celebrates every May. The signature drink swaps the Derby’s mint julep for a Black-Eyed Susan cocktail. It is, in the best way, our home version of the same beautiful nonsense.

Where to find one around here

You do not need to special-order from a London milliner. Boutiques around Annapolis, Bethesda, and Hampden in Baltimore stock straw hats and fascinators every spring, and local milliners take custom orders if you plan ahead. For a budget version, buy a plain wide-brim straw and trim it yourself — grosgrain ribbon, silk flowers, and a hot-glue gun will get you something genuinely lovely, the same crafty energy as my DIY Lilly Pulitzer pumpkins, just in pastels.

A Derby hat is permission to be a little grand. Pick the brim that loves your face, anchor it well, tie it to your dress, and wear it like you have somewhere important to be. And if you miss Louisville, I will see you at Old Hilltop in May. Throwing the party instead of going? My preppy party playbook sets the whole scene.