How to Don a Derby Hat

This Saturday, May 7, marks the 142nd running of the Kentucky Derby at Churchill Downs in Louisville. It’s a minor holiday at our house, complete with bourbon cocktails and a Southern menu at dinner.

Besides mint juleps and “My Old Kentucky Home,” what else do you commonly associate with “the run for the roses”? I’ll bet it’s ladies’ hats.

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Julep, a Houston bar on the east end of Washington Avenue operated by Alba Huerta, recently hosted “Hats Off,” a talk by Violet Peacock’s professional milliner Lindsay Halpin. The event was a lead-up to the bar’s Kentucky Derby party on Saturday. Here is some of what we learned about choosing the perfect hat.


Choose a hat most flattering to your face shape, says Halpin, highlighting five general face shapes.

  • Heart-shaped faces (think of Reese Witherspoon, Rihanna and Helen Mirren) are flattered by nearly any kind of hat, though it’s best to avoid very small hats, those with crowns narrower than your cheek bones (such as fedoras and trilbies) and very wide-brimmed hats. Go for medium-sized hats and those that are asymmetrical. Don’t over look fascinators, those tiny hat-like pieces that perch on the side of the head, picture hats, turbans and sailors.
  • Oblong faces (like Sarah Jessica Parker and Sandra Oh) should avoid tiny pillbox hats and tall crowns that will elongate the face even more, but are flattered by cloche (French for “bell”) hats and berets. Wide brims and flat crowns are a good style for longer and narrow faces.
  • Oval-shaped faces (January Jones and Naomi Campbell) can wear nearly anything, so experiment with lots of styles. However, if you are short, avoid very wide brims. Remember to keep the whole body in proportion with your hat. Ideal hats include cloches, berets, fedoras and boaters.
  • Square-shaped faces (Jackie Kennedy Onassis, Janet Jackson and Sandra Bullock) should avoid rigid hats, but look great in large floppy hats, soft lines, trims, flowers and asymmetrical silhouettes. Try on hats with upturned brims.
  • Round faces (Viola Davis, Charlize Theron and Fergie) can wear slanted fascinators, angular hats and tall hats. Avoid flat soft hats (like berets) and styles narrower than your face and opt instead for a high crown to add height and slim the face. Fedoras are your friend.

12472331_787393604693502_2272058276771146235_nPhoto by Monica Kressman Photography

When choosing a hat, pick a color that either suits your hair and skin tones or simply makes you feel good. The color may bring out your eyes, complement your whole outfit or pair with a scarf or shoes. Start simple, as a plain hat is easy to add to: feathers, a brooch, veil, flowers (real, silk or dried) and other trim.

When trying on hats, always use a full-length mirror and look at yourself from all sides, as well as from the front. A wider hat can balance out a bigger bottom while, in general, a brim wider than your shoulders is not a good idea … unless you’re going for a campy effect. What does the hat do to the back of your hair and collar? Will you be able to get into a car wearing your hat?


Finally, Halpin says that a woman’s sense of style is the most important aspect of wearing a hat. You must wear your hat with confidence – she calls it “hat-itude” – so never choose a hat that intimates you. Put it on, square your shoulders and own the world! Even if you’re not going to Louisville for this weekend’s big race, imagine yourself there and rock your hat.

Our Derby money, by the way, is on long shot My Man Sam (photo below).

Photo by Churchill Downs/Coady Photography