In preparation for the first Saturday in May, lets talk hats! The Kentucky Derby isn’t only about horses and gambling but also about fashion. I recently caught up with a good friend and hat designer, Satya Twena to get pointers on Derby-Style. She suggested to always to pick your hat first, then your dress.

This is a great tip since when it comes to derby-style the hat is the headliner act, so treat it that way. It’s easier to pick a hat to go with a dress than vice versa and don’t limit yourself to hats, feel free to wear a fascinator.  One other tip when prepping for the big race is to not match your hat to your outfit, a little color blocking can be perfect to help your hat to stand out.

I considered her suggestions and took to the streets to find great head pieces that’ll easily translate to everyday wear.  Let’s be practical, obviously we’ll want to wear our hats on those hot summer days.

Here are some great finds that’ll help you go from Derby to City-Chic:

1./7. Consider using fascinators! Check out this edgy downtown spike headband by Satya Twena and sweet frilly bow headband by Yestadt Millinery.

3./6. Loving this color-blocked pink brim hat by Yestadt Millinery.  Dress it up for the derby with a bright color dress like Blair from Gossip Girl or style it with shorts and a tank for a chic city look

5. DIY! Fold and pin a flower on this wide brim summer hat by Satya Twena for 2 different looks to carry you from the derby to the beach.

2./4./8. Who doesn’t love a straw hat? They’re perfectly paired with any sundress or beach attire yet the bow adds a little spice and enables you to dress it up amazingly for the upcoming horse races! These are fromThe Hat Shop NYC, Barbara Feinman, Yestadt Millinery.

9. And finally for the men, throw on any fedora or bowler and you’re guaranteed to look handsome. With the great line up at Barney’s, you have it easy. (PS- male styles for women, aka Ambit, as worn by Shayna can work too!)

Coverage by Chelsa Skees