Bro’s Guide To The 2016 Kentucky Derby And Triple Crown Of Horse Racing (What To Wear, Drink, And Watch For)

Bros! We’re just about a week and a half out from the unofficial start to drinking season. With the running of the 142nd Kentucky Derby on May 7th at Kentucky’s Churchill Downs, the first leg in the American Triple Crown of Horse Racing will kick off a new era of horse racing.

Until last year when American Pharoah raced his way into the record books we had been experiencing a 38-year-long drought of Triple Crown winners. The previous Triple Crown winner dates all the way back in 1978, with my distant relative Stevie Cauthen (my uncle’s cousin, true story) riding as the jockey aboard Affirmed. Now that American Pharoah has won the American Triple Crown of Horse Racing and revitalized the sport I fully expect the nation to embrace Horse Racing in a way that we haven’t seen in decades, and that starts with you bros going all out this year for the Triple Crown.

Because (1) I’m pretty into dressing to the nines for The Kentucky Derby, Preakness Stakes, and Belmont Stakes, and (2) I want to make sure you bros aren’t underdressed or ill-prepared for this year’s Triple Crown I figured I’d throw together a complete guide to this year’s Kentucky Derby and American Triple Crown of Horse Racing. Below you’ll find a style guide to the races (complete with suggest outfits), suggested cocktail recipes for each of the races, and a few blurbs on this year’s favored horses. Now let’s get to it…

The 142nd Kentucky Derby Race Info

LOCATION: Churchill Downs, Louisville, Kentucky
DATE: May 7th, 2016
PURSE: US$2 million (1st Prize: $1,425,000)
FAVORITES TO WIN: Mor Spirit, Gun Runner, and Nyquist
OFFICIAL BOURBON: Woodford Reserve
OFFICIAL COCKTAILS: Mint Julep and Blush Lily

The 141st Preakness Stakes Race Info

LOCATION: Pimlico Race Course, Maryland
DATE: Saturday, May 21st, 2016
PURSE: $1,500,000
FAVORITES TO WIN: N/A (same as Kentucky Derby for now)
OFFICIAL COCKTAILS: The Black-Eyed Susan
OFFICIAL BOURBON: Makers Mark

The 148th Belmont Stakes Race Info

LOCATION: Belmont Park, Elmont, New York (Long Island)
DATE: Saturday, June 11th, 2016
PURSE: $1,500,000 ($800,000 to 1st Place)
FAVORITES TO WIN: N/A (same as Kentucky Derby for now)
OFFICIAL COCKTAILS: Formerly the ‘Belmont Breeze’, currently the ‘Belmont Jewel’
OFFICIAL BOURBON: Knob Creek


Godinger Beaded Barware Beaded 4-1/4″ Mint Julep Cup (SILVER)

Mint Juleps are meant to be drank out of silver cups, and if you’re ready to get classy as fuck you can pick up a set for yourself. Or just buy one and drink out of a silver cup like a baller.

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And here’s the ‘Best Mint Julep Recipe‘, according to Esquire:

mint
1 teaspoon sugar
3 ounces whiskey — bourbon
old-fashioned glass

Place 5 or 6 leaves of mint in the bottom of a prechilled, dry 12-ounce glass or silver beaker. Add sugar and crush slightly with a muddler. Pack glass with finely cracked ice. Pour a generous 3 ounces of Kentucky bourbon over the ice. Stir briskly until the glass frosts. Add more ice and stir again before serving. Stick a few sprigs of mint into the ice so that the partaker will get the aroma.
Still not enough mint flavor? Try this: For each julep, lightly cover about 10 sprigs of mint with superfine sugar, add an ounce of spring water, macerate, let stand for 10-15 minutes, and strain through a fine sieve into the ice-filled glass. Then add whiskey and proceed as above. If you’ll stoop to maceration, you might also want to float 1/2 ounce of dark Jamaica rum on top.


Black-Eyed Susan Drink Recipe (Official Drink Of The Preakness) + Suggested Glassware

1 1/2 ounce Effen Vodka
1 oz of Makers Marks Bourbon
2 ounces Orange Juice
2 ounces Sour Mix
Garnish with Orange and Cherry

Suggested Glassware for the Black-Eyed Susan is a Highball Glass:

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Belmont Jewel Drink Recipe (Official Drink Of the Belmont Stakes) + Suggested Glassware

Suggested Glassware: rocks glass.

5 O’Clock Rocks Glasses (Set of 2 — $19.99)

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What To Wear At The 142nd Kentucky Derby, 141st Preakness Stakes, And 148th Belmont Stakes

Floral Printed Sportcoat From Vineyard Vines

In addition to being called ‘the most exciting 2 minutes in sports’ the Kentucky Derby is also referred to as ‘The Run for the Roses’. That name comes from the winning horse being draped in a floral blanket made of 554 red roses. The red rose is also the official flower of the Kentucky Derby.

Staying true to tradition Vineyard Vines released the Floral Printed Sportcoat that couldn’t be more quintessentially Churchill Downs if it tried. This is obviously pretty over the top, but if you’re a bro who likes to get after it on race day then this is the jacket for you! Know that this jacket’s selling out quickly though and sizes are limited due to extreme popularity this year.

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U.S. Polo Assn. Men’s Two-Button Nested Seersucker Suit

If you’re ever going to buy or wear a Seersucker Suit it might as well be for the Kentucky Derby, am I right? You can’t go wrong with this classic offering from U.S. Polo Association, and it just so happens to be 50% off (on sale) right now!

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North Valley Check Classic Tucker Shirt

With floral undertones, this shirt will lighten up your outfit no matter what colors you choose to wear to a Derby Party (or to the Kentucky Derby). You can wear this shirt with or without a blazer, and when the race is over it’s casual and will match with almost every single pair of pants you own.

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Dockers Men’s Long Sleeve Basic Solid Oxford Shirt

This is your basic blue button down shirt. You can wear with anything and wear it to nearly every event. If you’re not trying to go over the top this year then this is your shirt.

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Short-Sleeve Nautical Silks Pocket T-Shirt — Kentucky Derby Edition

This is your MOST CASUAL option. Ideal for a chill Kentucky Derby watching party that involves a full day of drinking. This shirt can be worn year-round and it’s comfy af.

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100% Silk Mint Julep Kentucky Derby Bow Tie

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Lillies Tie

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Mint Julep Tie

I own this one myself and I wear it to all three legs of the Triple Crown. Without fail, I get more compliments on this necktie every time I bust it out than all of the other ties in my arsenal combined.

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Men’s Equestrian Silk Bow Tie

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Horseshoe Woven Tie

If you’re going to wear this tie might I suggest wearing it with a non-patterned shirt. Plain colors only, it’ll make the tie really pop. This is also great for a farm/vineyard wedding.

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Seersucker Slim Breaker Pants

With these you either wear the matching jacket or you go without any jacket at all. Don’t try to mix-and-match with some random blazer from your closet because you’ll end up looking like a jabroni.

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Mint Julep Canvas Club Belt

This is the PERFECT belt to match those seersucker pants (or any other pants out there).

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Dockers Men’s Signature Khaki D1 Slim-Fit Flat-Front Pant

Your classic slim-fit khaki pants. You can dress these up or down depending on which shirt/tie/jacket combo you choose to go with. Just make sure to wear slim-fit pants so you don’t look like a frumpy asshole.

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Men’s Brown Soft Leather Belt With Gold Buckle

Usually I’d tell you to be very wary of wearing a brown leather belt with a gold buckle, but horse racing is one day that you can get away with it.

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Polo Ralph Lauren Men’s Vintage Western D-Ring Leather Belt

Since this is vintage there’s only ONE of these available for purchase. So if you’re interested in this unique/classic piece I suggest pulling the trigger, because this one’s going to sell out QUICKLY.

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Slim Breaker Pants — Jetty Red

Sticking with the theme of ‘roses’ for the Kentucky Derby, these ‘Jetty Red’ pants are PERFECT for the race track.

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Horseshoe Canvas Club Belt

As I did with the seersucker pants above, I wanted to suggest a belt to be worn with the Jetty Red pants. Here you’ll find the perfect matching belt for the occasion!

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Derby Straw Boater Hat

If you choose to wear a hat to the Derby or any other horse race then this is really the only acceptable style, if you’re dressing up. If you’re sitting down in the infield getting rowdy then shorts/jeans and a ballcap is totally acceptable.

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Steeples Pocket Square

You didn’t think I’d forget about pocket squares, did you? I can’t include blazers and not suggest some pocket squares for you bros!

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Horseshoe Geo Pocket Square

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Vargo Titanium Funnel Flask

I’m not ashamed to admit that I snuck in two full flasks to the Belmont Stakes last year. It’s not about trying to save money or anything, it’s because those lines for drinks can get insanely long at these events. Packing a flask is ALWAYS suggested.

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If all goes well I hope to see you bros back at the Belmont Stakes this year, and we can get another video like this one that I took last year of the crowd going nuts as American Pharoah won the Triple Crown:

Alright bros, I’m fairly certain I didn’t leave anything out in this year’s Kentucky Derby/American Triple Crown of Horse Racing primer. But if you have any questions left unanswered about what to wear, drink, or do then feel free to reach out to me direct by email at cass@brobibledotcom, or hit me up on Twitter at @casspa!

Kentucky Derby feature image courtesy of Shutterstock.com