How to beat the odds at the Kentucky Derby

It's the fastest two minutes in sports and one of the most fun events to witness first hand.  But even from afar, watching the Derby is momentous; and requires a certain savoir-faire. Having been involved with the race for years, we have assembled some tips for how to best enjoy one of our favorite weekends of the year including the who to follow for the best style ideas, what to drink and how to bet on the run for the roses. 

(1) Who to follow.  We're arm chair experts on the Derby, but to get first hand, real time coverage, it's worth checking out @FashionAtTheRaces. Bri is the founder of the brand and darling of the equine circuit. She has impeccable style and whether she's on the track in Santa Anita or standing in the winner's circle in Dubai, she is always wearing the chicest dress/hat/heel ensembles.  


Derby Style

Derby Style Hats

Derby Style Hats Heels Shoes Dress

Another to watch this year will be Manhattan's own @westvillagewasp.  Known for her stunning style in bold and bright colors, @westvillagewasp will definitely be one to watch at the storied hat contest.  Before you place your bets on any ponies, be sure to place a bet on @westvillagewasp to win this one. 

Check out some of their best looks for style-inspo:

Polo Hat Derby Style

Red Hat Horse Racing

Red dress polo derby style


(2) What to eat/drink.  The signature drink of the Kentucky Derby is the Mint Julep.  Made with Kentucky's signature bourbon, the cocktail is best served in its namesake tin cup and garnished with a fresh sprig of mint. 


  • .25 oz Raw Sugar Syrup
  • 8 Mint leaves
  • 2 oz Bourbon
  • Bitters (optional)
  • Mint Sprig
  • Glass: Julep (below) or rocks


  • In a Julep cup or rocks glass, lightly muddle the mint and syrup.
  • Add the bourbon and pack tightly with crushed ice.
  • Stir until the cup is frosted on the outside.
  • Top with more crushed ice to form an ice dome and garnish with a few drops of bitters, if desired, and a mint sprig.

3) How to Bet.   Gambling on horse racing is as American as apple pie.  There are two main rules of thought on gambling. Straight and Exotic.  

Straight wages allow you to bet on one horse.

  • WIN– You’re betting that your horse will come in first place. If your horse finishes in first, you collect.
  • PLACE– When you bet on your horse to “place,” you’re betting that he will come in first OR second. If your horse finishes in first or second, you get to collect. Payout for a place bet is less than a win wager, but you do have the security of being able to cash in if your horse finishes in the top two spots.
  • SHOW– You’re betting that your horse will come in first, second, OR third. Since you’re hedging your bets, you have a higher chance of winning, but the payout for a show bet is substantially less than a win or place wager.
  • ACROSS THE BOARD– When you bet across the board, you’re betting your horse to win, place, AND show. An across-the-board bet is what’s called a “combo straight wager” because it’s three different bets (win, place, AND show) in one. Across-the-board bets aren’t usually a good wager because they’re expensive and have less profit potential.
  • WIN/PLACE, PLACE/SHOW– Similar to an across-the-board bet in that you’re making multiple straight wagers in a single bet. In a win/place bet, you’re betting your horse to win AND place. If he wins, you collect both the win and place money. If he finishes second, you collect just the place money. 

Exotic Bets allow you to bet on multiple horses in a single bet, which increases your profit potential. But, these are much harder to get right.

  • EXACTA– You’re betting on two horses to come in first and second in an exact order. For example, if you placed a $2 exacta on horses 3 and 5, you can only collect if horse #3 comes in first and horse #5 comes in second. You can also “box” your exacta bet which means your two horses can come in any order in the top two spots and you still win. 
  • TRIFECTA– You bet that three horses will finish in first, second, and third in an exact order.  
  • SUPERFECTA– You bet that four horses will finish, first, second, third, and fourth in an exact order. As with exactas and trifectas, you can box a superfecta at an additional cost. The minimum bet is often 10-cents, which makes it more appealing to many people.

Horse Racing Style

Churchill Downs Style



Leave a comment

Please note, comments must be approved before they are published