A racegoer holds a mint julep via Getty Images
A racegoer holds a mint julep via Getty Images

There are a few events throughout the calendar year that are undeniable opportunities for you to flex a little when it comes to your choice in attire. The Kentucky Derby, which takes place at the famed Churchill Downs this coming Saturday, is one of them.

But don’t be fooled into thinking you need to adhere to cartoonish old-fashioned shit like head-to-toe seersucker or dopey hats. The Derby should be looked at as a chance to rock your best spring-appropriate semi-formal wear with just a little something extra to let people know you’re not messing around.

Below, a fit we wholly endorse.

Brooks Brothers

Patch Pocket Linen Sport Coat

Nothing too crazy here — just a nicely tailored, slim fitting linen sport coat that you should get an awful lot of use out of during spring and summer. Pair it with khakis, jeans, even a pair of equally tailored shorts if that’s your thing. This is the type of garment every man should have in his closet.

Brooks Brothers

Striped Oxford Button-Down in Green

A slight variation on the classic blue or white oxford cloth button-down that’s playful enough for the derby but still conservative enough for lots of other settings. Take note: we’re not talking about any no-iron nonsense here — this is pure, 100% cotton that’s gonna look a little rumpled by the end of the day, just as it should.

Todd Snyder

Fine Corded Sutton Suit Trouser in Pink

So here’s your flex for the day — light pink trousers that will no doubt earn you a few stares from the less sartorially adventurous folks at your Derby party. But fuck ’em, you know what you’re doing. The fine stripe of the fabric references seersucker without being too on-the-nose, and the color is suddenly very much in vogue after Seth Rogen was photographed wearing a dusty pink suit to a London screening of his new film, Long Shot.

Allen Edmonds

Wooster Street Penny Loafer

For our money, this new offering from Allen Edmonds is pretty much a perfect Penny: there’s no clunky beefroll to speak of, and the overall shape is elegant without being too pointy. Go for the walnut if you really want to stand out, but we recommend the more subdued cigar. Oh, and if you must wear socks … actually, don’t. And skip the belt while you’re at it.

Nota bene: If you buy through the links in this article, InsideHook may earn a small share of the profits.