9 Perfect Hats to Wear to the Kentucky Derby

Hats to Wear to the Kentucky Derby

Can you send me links to hats to wear to the Kentucky Derby or Gold Cup?” has been a constant question each year from friends who frequent the horse races.  Kentucky Derby and Virginia Gold Cup are less than two weeks away, which means it’s time get your liver ready for bourbon and mint juleps as well as watch horses run around the race track (if you make it out of your tent).  I’ve been attending Virginia Gold Cup for several years now and each year the most stressful part of going is finding the perfect hat for my outfit.  I usually go to the Garment District in NYC to buy wholesale hats because I can try on multiple options before deciding.

If you want a truly unforgettable hat, you have to be willing to spend some cold, hard cash.  Milliners like Eric JavitsSatya TwenaBijou Van Ness, and Christine A Moore have jaw dropping, statement making and one of a kind Derby hats and fascinators just for the horse racing season.

Choosing the right hat for the Gold Cup or the Kentucky Derby can be a daunting task. It takes creativity, thinking outside of the box and a lot of confidence to keep your head held high while wearing a Derby hat.  These hats exude the grandness of  the occasion and if you plan on entering one of the hat contests, you need to really think big.  For the girls out there just looking for a beautiful hat to go with your dresses, I’ve hand picked nine of my favorite hats in various price points for your consideration.

If you are in a time crunch, make a pits top at Forever21 or H&M and pick up one of the wide brimmed hats currently in stock.  Do a quick DIY by adorning the hat with ribbons, feathers, artificial flowers with a glue gun. Get creative in decorating the hat and don’t be afraid to go on  Pinterest to find some inspiration.

A few tips:

  • Yes you can wear a fascinator instead of a hat for the derby.
  • Yes you can wear flats instead of heels. Remember you are most likely going to be on your feet all day so comfort is key.
  • No you don’t have to wear florals or prints. You can wear a neutral outfit and go crazy with your hat or vice versa.
  • You can carry a clutch but remember to bring a cute tote bag or straw bag to carry emergency kit, i.e tampons, extra panties, makeup and brushes, booze, water, deodorant, hair brush, baby wipes and pain pills.
  • It is most likely going to be hot outside so keep your makeup light.
  • Bold lipstick can add some drama to your hat if you opt for lighter eye makeup.

Hats to Wear to the Kentucky Derby

Clockwise from left: San Diego Hat Company Sinamay Hat / Zara Flat Wide Brim Hat / San Diego Hat Company Bow Sinamay FascinatorPhilip Treacy Floral Sinamay Headpiece / Philip Treacy Upsweep Straw Leather-Trim Hat w/ Ribbon & Rosette Detail / Pamela Munson ‘The Audrey’ Hat /  Philip Treacy Flower Fascinator /Oversized Fascinator with Feather TiePamela Munson ‘The Fame’ Hat /

 

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