5 Expert Tips For Buying a Kentucky Derby Hat

Lorein Abenhaim

Pink and orange pill
Outside of the heart-pumping excitement that comes with fast horse races, the Kentucky Derby is a chance to dress chic from head to toe—emphasis on “head.” Like most activities that involve horses, this is one of those rare opportunities where it is essentially a requirement to sport a stylish hat.
With the Kentucky Derby taking place May 3 and May 4, you are probably thinking what we are thinking at this very moment—”I need a hat!” With so many shapes, colors, and designs to choose from, we sought out Leah Chalfen, owner of Leah C. Couture Millinery, for her expert advice. Chalfen learned her craft training with the head milliner of the Metropolitan Opera’s costume department and now focuses on designs that combine contemporary style with old Hollywood glamour. Her hats, all handmade, come decorated with feathers, netting, beading, and the most intricate of details. Here, Chalfen’s top tips to keep in mind when picking out a hat for the Derby.
1. Use Your Assets. “Since the Derby hasn’t placed rules on hat size like the Royal Ascot in England, we encourage people to wear what they like,” Chalfen shared. “A big brim is traditional, which can look very chic indeed if it’s trimmed tastefully. If you have beautiful hair, show off your hair, or if you have a long neck, show off your neck.”
2. The Sunglass Effect. “Since the Derby is a daytime event, usually with lots of sunshine, there is the undeniable sunglasses factor,” Chalfen says. “Take this into consideration. We think chic shades and jawlines are accentuated with a dramatic, smaller size hat.”
3. Coordinate Hat Color with Skin Tone. “I recommend a woman wear a color that suits her complexion no matter what color that is,” Chalfen says. “People must remember that headwear sits right next to your skin tone and your eye color. So it is essential to wear colors that compliment eyes, skin, and hair.”
4. Switch It Up From Day to Evening. “As the Kentucky Derby has been a hat-wearing event since 1875, the whole weekend should include hats,” Chalfen advises. “It’s always nice to freshen up after a fabulous day in the sunshine and change your ensemble for the next round of fun, which should definitely include a different chapeau. For the evening…opt for a cocktail size.”
5. Don’t Leave Home Without a Hatbox. “One should definitely have some type of hatbox, which would be given to you when you purchase a hat from a hat shop,” Chalfen shares on how to travel with your hat.