Kentucky Derby: Gentleman's Guide to Getting Lucky

The Kentucky Derby might be steeped in tradition, but if a significant portion of that is decadence, we'll reserve the right to sidestep it a little. This Derby season we urge you to indulge your inner Playboy and invoke those customs in a way that's more you riding the tradition than tradition riding you.

We wouldn't be Playboy if we didn't subvert something, so we've created this handy guide to help you do Derby Decadence in the vein of our own tradition.

Drinking | Dressing | Betting

We’ll let you in on a secret: Kentucky Derby style can run away with itself, and that’s putting it mildly. A simple Google search of men’s Derby fashion can lead you on a veritable Easter egg hunt as pastel suits, patterned ties and boater hats abound among well-meaning purveyors of tradition. It’s all well and good to fit in, but at what cost? It can all be a little cartoonish if you let it, but with style and a nod you can look the part without bucking the trend completely.

Suit...

If you’re going to do bold color, you can do better than borderline neon pastels. A properly tailored suit cut trim and sharp to your shoulders and chest, like this one from Richard James, can sing in true blue. It’s a fairly obvious riff on the trend that won’t put you in Mood Indigo. And hey, it’s Kentucky in May, so go wild and spring for the shorts.

Richard James Seishin Suit Jacket
Buy it now for $790

...and Tie

You’d be remiss to skip the opportunity to engage in a little peacocking. In lieu of ties sporting horseshoes, jockeys and stallions, pick up a pattern with a little more panache. Spring has sprung and it’s time to celebrate, so get wild and don some florals abstract enough to pass as camo, eye-catching for the right reasons.

Pierrepont Hicks Floral Tie
Buy it now for $60

Throw Some Shade

The Kentucky Derby isn’t all about mint juleps and society. There’s a race to be seen, no matter the glare from the sun on the verge of another Southern summer. These frames, in smoky quartz, will have you seeing clearly now, no matter how many cigars smolder over your shoulder.

Cutler & Gross D-Frame Sunglasses
Buy them now for $500

Toe the Line

Your Kentucky transgressions may have you treading on thin ice with the less genial gentry in your midst, so no need to step on every toe. This J. Crew Derby shoe—you read that right—is sexy in suede and a straight-up Derby traditional.

J.Crew Kenton Suede Bucks
Buy them now for $200

The Missing Link

We’re telling you now: you’re gonna wear a white shirt, crisp and classic and boring sans accoutrement. Accents, as we well know, can set an otherwise staid look apart. And since this party is a little bit Playboy…

Paul Smith Bunny Illustration Cufflinks
Buy them now for $145