Derby Decadence: A How-To Guide

By Playboy.com Staff

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<p>Kentucky Derby decadence is a game of chance. We'll show you the moves, it's up to you to make them work.<br></p>


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

Drinking

Dressing

Betting

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

The most exciting two minutes in sports is cause for celebration, which is itself cause for libation. Brew won’t do this time, folks, so sit back and relax with a cocktail made with the finest bourbon either side of the Mason-Dixon Line.

What can we say about a classic so ingrained that it’s the official cocktail of an American institution other than, “May we have another?” 

A cocktail after our own heart, the Ginger Julep puts a spicy spiral on the Kentucky Derby standby. And it’s just sweet enough to stomach another.

If you’ve got your eye on a certain prize, do the Derby good and offer her a jewel that doesn’t carry a colonial and two kids to match in its sweet aftertaste.

The Run for the Roses isn’t without its thorns. Your pick won’t always be a winner, so if you can’t be a sore loser you might as well be a sour one.

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

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

For those inclined to take indulgent behavior a step beyond drinking and dressing, there is gambling. And since we’re in the mode of breaking with tradition, we’ve highlighted a few pitfalls of the betting life. You may have faith in your winning wisdom however you employ it, but beware of a few common afflictions that could influence your choices in ways you might not even recognize.

High Risk, High Reward

Many bettors—and problem gamblers, at that—believe the only way to bet is big. And it’s true; you won’t win big if you don’t bet in kind. But the most immediate drawback to the practice is that high-risk bets limit the capacity to win at all—you’d have to bet a large sum on the chance that a single horse will place a specific way. And since this is chance, and there are any number of variables at play, probability tells us we’re far more likely to lose it all than win anything.

No Playing Favorites

Further to the impulsive habit of slim-to-no-win betting is a superstition against placing bets on the horses tagged most likely to succeed, whether by public favor or statistics and track record. Bettors subscribing to this particular fallacy mistakenly believe the novelty of their choice—the fact that fewer people might be making it—will increase its luck. Stats might not always pull out, but they often do, and betting with the crowd is more likely to yield positive results than betting against it.

Don’t Follow the Undefeated

But if there’s one stat experienced bettors will follow, it’s the negative type, the type that informs us of a bad omen even, again, in the face of track record. It needn’t even be mentioned in certain circles that only eight horses who’ve entered the Run for the Roses undefeated have taken off with the title. So lucky streak or not, there’s not a chance in hell the pros of betting will lay their money down on this year’s unchallenged entrant, Verrazano. Unless, of course…

The Name Rings a Bell

This one is so tried, it can only be true: there’s something to be said for the power of association. Gambling being an impulsive and, some might say, dangerous behavior, the power of personal pull can be impossible to maneuver around. Verrazano, the aforementioned potential front-runner at this year’s Derby, is named after the suspension bridge that connects Brooklyn and Staten Island in NYC. Never mind the empire state of mind that lends the name power, how many people, native or otherwise, do you think have very personal attachments or experiences associated with that name? If that isn’t a loaded choice of nomenclature, we don’t know what is.

With Women Present

We’ll include, and finish, with this one only because it offends us to our very core. Perhaps more prevalent in cards-based gambling than in horse racing, but present nonetheless, is the belief that having a woman present during betting or play will jinx it. Gentlemen, if you’re a subscriber to this belief, we have one thing to say to you: it’s called getting lucky for a reason, so don’t hedge your bets.


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