Page 1 of Hats off to Love

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If you ask anyone to describe the great state of Kentucky, odds are they’ll most likely answer you with “Bourbon and horses,” but if you ask me, the only thing I’ll ever respond with is “Derby hats.”

Big hats. Small hats. Elaborate hats. Simple hats. Elegant hats. Vintage hats. Statement hats. Bright hats. Pastel hats. You name it, I love them all. Every. Single. One.

I’m not sure when or where I was the first time I saw a Derby hat. Growing up in Louisville, they’ve always been a part of life. From the first Derby back in 1875 to today, every spring, as the dogwoods blossom and the tulips bloom, so begins the Derby season and so begins the quest to find the perfect Derby hat. After all, the Derby might be the most exciting two minutes in sports, but before and after the race, it’s all about the parties and the fashion. The who’s who of the thoroughbred racing industry will step out dressed to the nines, along with the many celebrities and influential individuals who come to be seen.

It’s my absolute favorite time of the year, and because of that, I’ve always known I would one day open my own Derby hat store. Now, at twenty-five, my dream has come true.

“Do you think it’s too big?” asks the woman standing in front of one of the shop’s ornate silver full-length mirrors as she twists her head from side to side to get a feel for how sturdy the hat is.

“Honestly, you’re asking the wrong person. To me, a Derby hat can never be too big.” I smile at her while smoothing down a long black feather from another hat she tried on.

Her eyes find mine in the mirror, and she smiles back. “I suppose you’re right. Plus, they all seem to be about this size.” She glances at the counter where several hats she’s tried on sit, varying in color and style.

It was after many months of planning and preparation that I opened Rosie May at the beginning of the year. Yes, I used my actual name, but I love it, and in many ways, it defines the Derby.

My mother grew up going to the Derby and has always loved the “run for the roses,” which comes from the blanket of roses they drape over the winning horse and is how I acquired my first name. Since our last name happens to be May, the same month the race is run, it’s really just perfect for my little boutique shop in the East Market District of downtown, which is also referred to as NuLu for new Louisville.

Could I have come up with a fun hat shop name? Absolutely, but I want Rosie May to be a brand, a label that one day is recognizable and sought out.

“Okay, I think I’ll take it.” She beams as she claps her hands together.

“I think you’re going to look stunning,” I tell her, and I mean it. She selected one of my favorites this season, a navy hat with arranged navy and pink feathers. On one side there is navy netting that supports the smaller feathers as they alternate in color to resemble a full gorgeous flower, and then there are the long feathers that arc up over the hat to complete the look.

“Now I just need to find a dress,” she murmurs with a laugh. She’s completely delighted with her selection, and my hat-loving, people-pleasing heart squeezes with pride and satisfaction.

It used to be that women would find the dress first and then the hat, but the tide is shifting with the elaborate ways hats are being designed. The declaration is the hat, not the outfit or dress, which sounds great to me.

She hands me the hat, and I carefully take it to the back counter to pack it up in a large light pink Rosie May hat box. She swipes her finger across the purchase screen and lets out a delighted squeal as she reaches for the thick satin twisted cord of the box.

“Thank you so much for coming in, Kelli. I really appreciate your business.”

My gratitude is sincere. When someone opens a business, odds are they really have no idea how it’s going to go. I wasn’t sure what type of reception I would be given this Derby season, and I’ve had many sleepless, anxious nights. It’s my first season, and I’m a brand-new, no-name shop. With every purchase, I still find myself surprised people came here to buy one of my hats. It’s humbling, but it also gives me confidence in this risk I took.

“No, thank you! I’m so excited I can barely stand it. I knew I’d find the perfect hat here.”

“That means a lot to me.” I lean forward as if I have a secret to share, and she mirrors my posture. “Don’t forget to send in your friends.”

She stands back up and laughs.

“Let’s do one better—take my picture?” She turns and points toward the front of the store where I covered a section of the wall from ceiling to floor in roses of varying shades of pink. It’s the perfect backdrop for social media pictures and includes a neon sign that says, A rose is a rose is a rose. -Gertrude Stein.

“Of course! But it’s better if Molly takes it—she has the eye for these things.”

Upon hearing her name, Molly pops up from one of the four tables I have placed in the middle of the store where she is working on her laptop. In addition to people coming in to try on the hats, I wanted to enhance the experience, so I added the tables with matching high-back light pink patterned chairs and hung a gorgeous crystal chandelier over each one. For a small fee, the customers can order a pot of tea and a scone, which I buy daily from the bakery down the street, complete with Devonshire cream and jam.

I love the charming and classic feel the tea time brings to the store. It’s an ode to my mother and one of my favorite childhood memories. We used to dress up in our Sunday finest, don our most favorite hats, and drink tea.

“Great, you can be in one with me,” she says as she makes her way toward the wall.

“I do love taking photos,” Molly says.

Molly is my best friend and also runs her own marketing company. Of course I hired her, and what she’s done with the Rosie May branding, the logo, the website, the ads, and social media—all the stuff I have no clue how to do—it’s amazing.

I watch as she perfectly places Kelli in front of the wall, has her extend her arm straight out in front of her so the hat box dangles off her fingers—putting my name front and center—and takes the photo.

It’s brilliant.