There are many who would argue that a hat is a requirement for an event like Gold Cup. While I agree that there are so few opportunities to wear a hat that you should take the opportunity when it is presented, not everyone looks good in hats. (I look like a Russian Nesting doll in a hat, it’s not cute.) But for those of you looking to wear a hat, there are many styles to choose from.
While by no means traditional, this pork-pie hat would look adorable with a flowy white sundress ala Governor’s Island.
A turban, like this beige, floral number, is also a different style of hat to consider. It would be especially pretty on someone with strong features to balance the roundness. Also, you could style your hair in a low bun for a slightly flapper vibe. And since it’s beige, it can be paired with many different colors.
In natural or black, this sun hat is very simple and traditional. It works very well with sundresses and on most face shapes. You can also add a ribbon or brooch to add a little embellishment. If you plan to wear navy and you have a little coin to spend, you might try this hat from Proper Topper.
If you’re like me and hats are not your thing but you don’t want to be unadorned, you can try an embellished headband. Whether it be floral, sequined or feathered, these headbands add a splash of color and texture to any attire.
If you want the full Kentucky Derby experience, you can try a hat like the one above. Because unless you marry the heir to a horse racing stable or get a job at Churchill Downs, this may be your only opportunity.