Saturday is the Kentucky Derby and it’s that time of year when horse racing comes to the forefront of our minds. If your heading down for the races, you should already have your look picked out but if you haven’t yet, I have a couple of suggestions for your race race day look.

Even if you’re not heading to the Derby, there is still time to grab your race day look and enjoy some other horse racing events. Washingtonians may not flock down to Churchill Downs but on the same day many head to Great Meadows in The Plains, Virginia for the Virginia Gold Cup. A race day look is just as appropriate here as it is down in Kentucky. And the kicker? People here are just as festive.

Washington is also in close proximity to Pimlico Racetrack in Baltimore. Just two short weeks after the Kentucky Derby, the Preakness hits this famed raceway, which hosts the second leg of the Triple Crown. Since it’s just a short drive to Baltimore from Washington, this is another ideal event to sport a race day look. Naturally if you’re attending both the Gold Cup and the Preakness, you cannot wear the same race day look twice.

Need some style ideas? Check out these selections.


The Relaxed



The Risk Taker



The Sophisticate


Got your look? Now enjoy your races with a great cocktail from I. W. Harper. Here are a couple of cocktails to whet your whistle.

Whiskey Smash

1.5 oz. I.W. Harper Kentucky Straight Bourbon Whiskey

Simple Syrup




Mint Julep 

1.5 oz. I.W. Harper Kentucky Straight Bourbon Whiskey

1.5 tsp. cane sugar

Fresh mint leaves



Shop My Look/Details

Plaid waistcoat – Suit Supply; White dress shirt – J Crew; Chambray slacks – J Crew; Blue tie – Bloomingdales; Spectator shoes – Brooks Brothers (saddle shoes – G H Bass); Fedora – Goorin Bros. (similar)



I am working in partnership with I. W. Harper Kentucky Straight Bourbon Whiskey and I am being compensated for my participation in this campaign. All thoughts/opinions are 100% my own. Whiskey is intended for those whom alcohol is legal and appropriate. Please Drink Responsibly.