How Do You Derby? 5 Locals Share Their Kentucky Derby Traditions

April, 2018

Do you buy a big hat? A new bowtie? Do you only bet on horses that have funny names? The Kentucky Derby is all about tradition. Every season the Louisville community can expect excellent food at the Chow Wagon and the fastest two minutes in sports. But how do Louisvillians “do” the Kentucky Derby? We’ve rounded up a few notable Louisville residents to share their traditions, new and old, with us. Here’s how five locals derby!

5 Locals Share Their Favorite Kentucky Derby Traditions

Lee Robinson, The Lee W. Robinson Company

Lee Robinson of The Lee W. Robinson Company offers Louisville residents a “one-stop shop” for residential design, architectural drafting, renovation, construction and interior design services. Image: The Lee W. Robinson Company

What are some of your favorite Derby traditions or unique celebrations?

Mint julep cups and Kentucky fare at any events I attend. Country ham biscuits, beef tenderloin, corn pudding — traditional Kentucky menu and beverages.

What is your go-to attire for Derby?

Something very dapper and traditional.

If you do not head to Churchill Downs for Derby-time celebrations, what is your favorite restaurant or meal to enjoy around Derby season?

I love Derby brunches.

Who are the people with whom you enjoy celebrating most?

My wife and my three sons and out-of-town guests who get a kick out of their first Derby.

What is your favorite part of the Kentucky Derby season?

The parties.

Chelsea Collard, Director of Marketing, Kentucky Select Properties

Chelsea Collard is the Director of Marketing for Kentucky Select Properties, Louisville’s 100% locally owned and independent residential real estate company. Image: Rachel Moore

What are some of your favorite Derby traditions or unique celebrations?

I have a tradition of always buying a Derby pin and the souvenir glasses. I have one from every year since I was born! I also love the tradition of going to Thurby, which is just as much fun as Derby, but not as crowded.

Do you always attend the Kentucky Derby? If so, what is the longest running consecutive attendance?

Not always, but off and on over the years. For the past five years, I have attended.

What is your favorite restaurant or meal to enjoy around Derby season?

Derby pie! I always save room for a slice — or three!

What is your go-to attire for Derby?

A brightly colored dress and, of course, a hat or fascinator! Shoes are the tricky part — will it be raining? How far will I have to walk? Will I be standing on grass, dirt or concrete? So many factors go into my Derby shoe selection.

Do you have any gambling superstitions?

I don’t know much about gambling, but if the track is sloppy, I always bet on the long shot. This kind of track condition really levels the playing field, and if my horse wins, the payout is much more significant!

Who are the people with whom you most enjoy celebrating?

Friends who share the same enthusiasm for Derby and casual gambling as me.

What is your favorite part of the Kentucky Derby season?

The whole month leading up to Derby — the city is so clean. There are so many events going on, and residents are just really proud of our city, so it is a great time to be in Louisville.

Kelli Bauman, Brand Associate, Coopers’ Craft Bourbon

Kelli Bauman is the Brand Associate for Coopers’ Craft Bourbon. Image: Kayla Darbyshire

What are some of your favorite Derby traditions or unique celebrations?

Every year my in-laws host a Derby celebration. I still haven’t had a chance to attend Derby, but my husband and I have attended Oaks and love it!

What is your favorite restaurant or meal to enjoy around Derby season?

Is bourbon a good enough answer? The mint julep is the official drink of the Derby and our sister brand, Woodford Reserve is the official bourbon of the Derby. Whether your mint julep is made with Woodford Reserve or Coopers’ Craft, it is the perfect and most delicious way to celebrate Derby.

What is your go-to attire for Derby?

Even though I do not attend the Derby, I still enjoy getting all dressed up for our family Derby party. Usually a colorful dress (likely from Dress & Dwell) is my go-to.

Do you have any gambling superstitions?

Now that I think about it, the past few Derby celebrations I have worn pink and not won. So maybe this year my superstition will be to not wear pink!

Who are the people with whom you most enjoy celebrating?

Family and friends. My husband comes from a large family, and my in-laws know how to celebrate Derby the right way. Our Derby party is always a good time — mint juleps, a huge spread and a little betting!

What is your favorite part of the Kentucky Derby season?

The Trifecta of Derby Season: Coopers’ Craft Bourbon. Dresses. Family.

Heidi Potter, Freelance Writer, StyleBlueprint Louisville

Heidi Potter is a regular StyleBlueprint Louisville contributor. Image: Adele Reding

What are some of your favorite Derby traditions or unique celebrations?

My favorite Derby tradition is when the contenders are listed in the Courier-Journal in a big racing form. We pull out the page and our whole family makes bets on our horses. I can predict from the minute I see the page who my kids are going to bet on.

Do you always attend the Kentucky Derby? If so, what is the longest running consecutive attendance?

While I don’t always attend the Derby itself, I have never missed going to either Oaks or Derby one time in 20 years. We used to do both Oaks and Derby, but that was when I was young and had better stamina.

If you do not head to Churchill Downs for Derby-time celebrations, what is your favorite restaurant or meal to enjoy around Derby season?

It used to be the patio at Azalea’s, which cannot be replicated for the experience around Derby time. I’ve been to Jack Fry’s on Oaks night, and that was amazing. Now we just try to go somewhere a little quiet where we can get a reservation, or we go to someone’s house for a casual dinner.

What is your go-to attire for Derby?

That’s a great question, one that I do not have an good answer for. I usually buy my Derby dress(es) around Christmas in my hometown of Houston, TX. I hate seeing my dress coming and going at Derby on other people, so I shop early and out of town. But last year, I bought and returned an entire outfit, because it was too cold and ended up wearing a comfy warm dress and boots.

Do you have any gambling superstitions?

I am lunacy-level of superstitious, just ask anyone on my tennis team. But my biggest superstition is that I don’t tell anyone who I am betting on before the race. I have a friend who does the same, and we are usually lockstep in our betting picks, but we won’t tell each other until after the race. I place my bets like I am receiving a sign from God: The horse has a name that’s in my family, I know the owner, he’s my lucky number. God speaks to me in that racing form, and while I’m not always interpreting the vision right, I have won big a few times.

Who are the people with whom you most enjoy celebrating?

After 15 years of entertaining clients with my husband’s business for Derby, I could have fun with just about anyone. We don’t entertain anymore, and I have a whole new level of gratitude for going with my friends and not for work. I also love taking my big family from Houston because they are like kids in a candy store here in Louisville.

What is your favorite part of the Kentucky Derby season?

The fact that for something that only lasts two minutes, the city builds a month of prep and celebration into it. My other favorite thing is watching Terry Meiners broadcasting live in the infield first thing in the morning on Saturday. It is television gold.

Would you like to add anything else?

Twenty years ago, my former neighbor, who was a 90-year-old spitfire, told us that we would only “sleep in the box” during Derby time. That means sleep when you’re dead, because you can’t miss anything during this special time. Do everything: the balloon glows, run the mini, go to the Chow Wagon, go to the steamboat race, go to the fireworks, go to the parade. I did everything with my kids from the time they were infants and wouldn’t do it any differently. Now that they’re older, they just ask us how many days Derby week that we will be gone! Go, baby, go!

Shannon Kessler, Stylist, Primp Style Lounge

Shannon Kessler is a stylist at Primp Style Lounge, which offers hair styling, personal wardrobe consulting and makeup application. Image: Whitney Neal

What are some of your favorite Derby traditions or unique celebrations?

Every year, my best friend and I host a Derby brunch the Sunday before Derby. Forty women gather at my house to kick off Derby week. We cook all the food, and use our grandmothers’ china that has been passed down. It is my absolute favorite Derby tradition.

Do you always attend the Kentucky Derby? If so, what is the longest running consecutive attendance?

I don’t get the chance to attend the Derby every year. However, I do attend other days at the track during Derby week, like Thurby and Oaks.

What is your favorite restaurant or meal to enjoy around Derby season?

Jeff Ruby’s is my local favorite, serving fantastic food with a really cool vibe. It’s the perfect place for a great meal, and you may bump into a few celebrities while you are there. I have to have a slice of Derby pie, or it’s just not Derby!

What is your go-to attire for Derby?

I love a fascinator! They are a little easier to wear and not as heavy as a traditional hat. I like to take risks in my Derby attire. Last year I wore a vintage lemon jumpsuit with a custom lemon “hatinator” — if a hat and a fascinator made a love child, it would be the hatinator. A dress is an easy option and a classic staple. In years’ past, I have worn rompers, tweed shorts, skirts and dresses.

Do you have any gambling superstitions?

I am not great at betting on horses. If I do place a bet, I like to pick the Jockey wearing pink and the horse with the name that makes me giggle. The money I save from not betting, I spend on my fascinator.

Who are the people with whom you most enjoy celebrating?

My husband Dan and my friends.

What is your favorite part of the Kentucky Derby season?

The best part of Derby season is the excitement that fills the air! Starting in late March, early April, Louisville starts to buzz with talk of Derby. It feels different, almost electric. I love getting questions about style trends and hat ideas. We are really lucky to have such an authentic experience in our city.

Would you like to add anything else?

One of my favorite things to do at Derby is visit the “Derby Village.” This is the area across the street from the track where locals sell everything from parking spots to home-cooked ribs to flip-flops. I have eaten some of the best food there, made with love and all kinds of spice! Your Derby experience is not complete without a trip to the “Derby Village.”

Thank you to our Louisville residents for sharing their traditions with us!

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