The Right Hat Gives Derby Day Confidence

Mint juleps and the run for the roses may make up sport’s most exciting two minutes, but choosing an outfit for a Kentucky Derby party could spell disaster. Who wears hats these days?

Thankfully, I had two local experts to help me dress for my first Kentucky Derby party at Austin’s lovely Hotel Ella.

Derby Day Hat
No, I’m not breaking the Internet, but that’s a lot of Instagram interest for me. I never do clothes stuff!

Pick the Hat First

Not being a style blogger, Kardashian sibling, or British royal, I was stumped — where would I find a hat in Austin (clarification: not a cowboy hat)? A bit of Googling uncovered a wonderful shop I’d visited years ago, Amelia’s Retro-Vogue and Relics.

About two weeks before the party, I paid a visit. The owner, Jane Clarke,  advised on styles, honestly critiqued, and shared all sorts of wisdom and useful knowledge. Especially helpful was Clarke’s direction on just where to place various hats on the head and how best to handle and store them (by the crown and upside down).

Originally, I was drawn to a dark brown number in keeping with more contemporary Kentucky Derby styles. It was a bit pricey and, while I liked it and it suited me, I wasn’t in love. Clarke, exceedingly patient, encouraged me to try on everything, which opened up some unexpected options.

One hat was a complete surprise. If someone had said beforehand, “You’ll wear a small pastel number topped with flowers that sits sideways on your head,” I’d have rolled my eyes and scoffed. Yeah, right.

I wound up leaving with a subtly dramatic sculptural piece from the 1930s. Because of the flowers on it, I even got a price break (April’s discount, woohoo!).

The purchase felt like a bold move. Knowing that no one would be wearing anything like it alternated between exciting and frightening.

Work the Outfit Next

Derby Day at Hotel Ella
My good friends Tina (left) and Tara (middle) are always up for a dress up night out. Photo Credit: James Nyfeler

Pairing the wrong clothes with this special hat had potential for clown-like disaster. Adding pressure: I was attending the party with two dear friends who are always impeccably dressed and stylishly put together.

First, I played around with colors. Revealed by its underside to have once been pink, the hat had faded over the years to a muted mauve, with undertones of tan and coral. The wise choice seemed to be picking a complimentary color, so that the hat accentuated the outfit (matchy-matchy is so out).

Lately, I’ve been in love with navy. Yes, I’d focus on the navy flowers for my base.

While I enjoy nice clothes, I usually hate to shop. My go-to resource these days is a small off-season designer boutique on Burnet Road, Spring Frost. It’s named for the owner, Spring Frost Castillo, who I adore. Spring feels more like a friend than merely the boutique’s owner, and her staff focuses on exceptional customer service.

Hanging in the closet from my latest visit to Spring Frost were a white Susana Monaco pencil skirt and bobi sleeveless tunic in navy. Both are simple, light, comfortable, and modern. I paired the skirt and tunic with some navy kitten heels by Rampage and rose gold jewelry (an open collar necklace and hoop earrings).

Have a Great Time

The party was a blast, largely because I felt amazing in my one-of-a-kind hat and sleek outfit. And it’s all about the good time, right?

Hat Selfie Fun
At least our selfies capture the fun. Photo Credit: Tina Haskell
Derby Day Man Style
My husband James (right) put together his own outfit, complete with natty bowtie and adorable pocket square. Tara’s husband Mike works the Austin gentleman look.

Our guys enjoyed the night, too. As at any Austin event, all styles were welcome (and present) under Hotel Ella’s giant lawn tents. I realized that any fear over an outfit was unnecessary as well as completely and solely self generated.


If my hat and clothes made me happy, they were good enough to wear.


I think I need to find more reasons to wear that hat.




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Published by Leah Nyfeler

I'm a writer, editor, runner, and adventurer who is always looking for the next new story, exciting adventure, and good meal/book/movie. My focus is on helping people find their best, healthiest self through sharing what I know and how I've come to learn it. In addition to my blog "Enjoying the Journey: Observations on the Fit Life" at, my articles have appeared in a variety of print and online magazines. You can hear me as part of the 2015 Austin cast of Listen To Your Mother.

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