Kentucky Derby: The Comfort Zone

This year, Derby style is evolving from simplistic peplum dresses to multiple shades of seersucker. You no longer need to subscribe to boring florals and tan chinos from your closets.  Let’s update your prints and invest in trousers your date can be proud of. We are going flirty, bold and monochromatic this season!

What do people wear to The Kentucky Derby is thee second most topic of conversation after who won the race. The third, is what we actually wore! What locals call ‘The Derby,’ is one more opportunity to take our Sunday’s best straight to the winner’s circle.

Every week leading up to The Run for the Roses I’m teaming up with celebrity stylist and fellow KYian Ben Wills on how to find the best style options this race season. You can find  her at or iBenwills on Instagram.


In 142 years of The Kentucky Derby, men have been uniformed in everything from seersucker to multiple shades of khaki chinos paired with collegiate navy sport coats. This years debonair gambler is wealthy and sophisticated, not stuffy; he is hip yet traditional. This 143rd year, our guys are exchanging their country club uniform for an updated cowboy’s preference.
Items You’ll Need: Be sure to click your favorite items for direct purchase.
Kentucky Derby: The Comfort Zone


What look do you enjoy the most during the Kentucky Derby? Sound off in the comments below.

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