Woman in Green Hat

What Hats Do I Wear to the Preakness

Hats come first, in all things, but especially when getting dressed for a big event. The hat will dictate the shoes, and then the whole rest of the outfit will fall together in between, I promise. What kind of hat do you need to kick off your outfit? From the classic wide-brimmed hat to the humble cloche, the sky is the limit.

Big Brim Hats

A perfect place to start, of course, is the wide-brimmed women's dress hat. This is the hat style that most people think of when they think of the horse races, and is available in an enormous variety of colors and materials. 

Now, while “go big or go home” is the attitude of the day for the horse races, depending on where you are seated, you might find that the wide-brimmed hat can take up just a little bit too much space. This can be double true if you are going to the Preakness with some like-minded hat enthusiast wearing similarly large hats, or if you find yourself next to someone who is as stylistically gregarious as yourself.


Under those circumstances, lots of people reach for a fascinator. Charming little details on headbands, a fascinator is a perfect way to accent an outfit, or to coordinate with other accessories. While the wide-brimmed women’s hat, with all its ribbons and bows, is best worn as the focal point of the outfit, it also keeps the wearing from having too many other accessories, leading to a more plain outfit. The fascinator, through its small size, avoids these pitfalls, and allows the wearer to spread details and points of interest throughout the outfit. It also allows the wearer to maneuver through crowds much more easily, as it keeps it’s footprint to a minimum


If it’s a proper hat that you want to wear, but you want something a little bit smaller than a wide-brimmed hat, or if you like a little something a little bit more vintage, look no further than the cloche. While it is easy to think of the cloche as a winter style, the cloche can in fact be found in a wide variety of materials and colors appropriate for the Preakness. A rough panama straw with a madras bow can be extremely charming, and lends itself well to a more casual sundress, where a finer straw or paper weave is extremely elegant when worn with a grosgrain hat band and bow.

Whatever hat you end up wearing to the Preakness, or to any of the other horse races, our hat is off to you. You’ve become part of the ongoing hat tradition that we are so happy (so very hatty) to be part of. If any more advice is needed, you are always welcome to stop into one of our locations, where someone will be more than happy to talk you through the finer points of dressing for the Preakness, or to show you how to achieve the original “derby swoop.”