What to Wear on Derby Day

Whether you’re at Churchill Downs or here at Woodbine racetrack, derbies are the one sporting event where sartorial peacocking is encouraged. As any racing enthusiast knows, the real competition off the track is found in the stands. So, dust off your bowler hat and get ready to rock some pastel in the spirit of high stakes this Derby Day. And what better way to get you ready than to inspire your inner Southern dandy with lessons from the likes of Jay Gatsby, James Bond, Gene Kelly and Don Draper.

To bring an air of debonair to the derby, a sports coat or tailored suit jacket is an absolute necessity. Whether you opt for seersucker, madras, or just a classic blue suit, you’ll look like you mean business when placing your bets. Leave the dark horse for the racecourse and don’t feel confined to neutral colourways in your jacket, let some colour grace your shoulders.

Neutrals do, however, have their place in your ensemble. A white or blue oxford button down is the perfect canvas for a bold suit (you can always opt for a more polished fabric though). Play with proportions and let the shirt’s cuffs peep through, and if you’re truly committed to the highbrow haught of Derby Day, go for gold with a pair of cufflinks. A plain base layer also allows for pattern play to pop when it comes to your neckwear. Embrace the flamboyance of a silk bow tie (self-tie of course) and let a dash of bright colour bring out your inner jockey.  

Now if the weather’s right, things can get a little heated in the stands as you wait for Seabiscuit to take the crown. That’s why a wide brimmed hat and a pair of classic shades are a good idea to keep you cool and dry. Shades are there for you to maintain whatever your mint juleps manage to betray. On the other hand, panama hats allow you to safely bask in the sunlight as potential glory ensues.

Derby Day wouldn’t be derby day without a pair of derbies for your hooves. As the Gentleman’s Gazette would suggest (taken with a grain of salt), the Derby shoe itself originates with the 14th Earl of Derby. His bootmaker designed an open-lace shoe to accommodate the portly chap’s wider feet, and thus was born the ultimate comfort shoe. There may not be any dressage on the track, but don’t forget about how your own socks will factor in with your look, those bad boys will put on a show when you take your seat.

Now, while there are some rules in place, Derby Day is your chance to let your sartorial choices amplify your personality. Often considered a style-apocalypse of sorts, Derby Day is the place to take risks and try something new in your style choices. And even if you’re not a winner on the course, dress like one.

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