The super rich spend up to $1,000 on a Kentucky Derby hat—here's what it's like to shop for one

How to shop for a Kentucky Derby hat like the super rich

The "most exciting two minutes in sports" wouldn't be what they are without the flashy, extravagant hats. Donning fancy headpieces has been a Kentucky Derby tradition for decades and became even more popular after the royal wedding in 2011.

So when I found out last-minute that I'd be attending the iconic horse race on Saturday, I knew I needed something elaborate to fit in.

As I am a Derby and a headpiece rookie, I headed to a millinery in Downtown Manhattan, to consult an expert: Lisa Shaub. She's been making hats for 30 years and has even worked with celebs like Taylor Swift and Britney Spears.

The first thing Shaub asked me is what color I'll be wearing. I have a white dress, so that left us with an array of options.

When hat shopping, you want something "that is working with you and not overwhelming you," she told me, and that looks different for everyone: "Some people are really tall or really dramatic. Some people are really small with a tiny little face. Different people have different needs, so I make different kinds of shapes for everybody."

The traditional derby hat is a big, wide-brimmed hat with a big flower, but Shaub is known for her fascinators and that's what she recommended I wear. A fascinator, I learned, is a smaller, more lightweight headpiece that fits on the head with an elastic.

Festive hats at the 2015 Kentucky Derby
Elsa | Getty Images

Shaub has been working on derby-specific hats since January. While most of her clients set up appointments for custom-made hats, she always has walk-ins the week leading up to the Derby and even on race day. This Saturday, she'll be in the shop at 9:00 a.m.

"Everybody is a procrastinator," she said, and while she'll get calls for derby hats as early as February, "most people are coming in after April 15."

Each hat takes a couple of weeks to make but the extravagant ones are even more time consuming. One of the most complex ones Shaub has made for the Derby was for comedian Tracy Morgan's wife, Megan Morgan, pictured below.

Another memorable derby hat, said Shaub, is the one she made last year for Maryellen Bonomo, owner of the 2017 Kentucky Derby winner, Always Dreaming. Shaub, who wasn't watching the race, remembered getting a call from her mom right after Always Dreaming clinched the race: "She calls me and says, 'You have to turn on the TV!' And there she [Bonomo] is, in my hat, being interviewed!"

The Kentucky Derby is like Shaub's Super Bowl, or "millinery Christmas," as she put it. "It's fun to see everyone dressed up. I love to see people being really creative and expressing themselves, so it's nice when people have a license to do that."

And it's inspiring to see how the super rich do the Derby, she said: "People that are really going, they've spent thousands of dollars on their outfit."

Racegoers wear derby hats on the eve of the 2017 Kentucky Derby
Bloomberg | Getty Images

The headwear alone can cost up to $1,000. And those who also attend The Kentucky Oaks, the sister race of the Kentucky Derby held at Churchill Downs on Friday, are often buying two different hats, one for each event.

Shaub's pieces range from $95 to $700, and she said the average Derby racegoer will drop $475 on one hat.

They're all out of my price range, but I couldn't resist … and I needed something. I shelled out a couple hundred dollars on a piece that Shaub called "modest and sweet." She added: "You're a new hat wearer, so you may feel more daring next time."

I feel pretty daring in the bright pink fascinator, and a bit fiscally irresponsible, but I also feel as ready as I ever will be for Saturday.

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