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On January 26, I saw my first listing for a used Derby hat on a swap site. It was a beautiful designer hat and would make somebody’s outfit perfect … in more than three months from the sale date. That seems crazy to anyone who is not from Louisville – buying something that far in advance. But I thought it was genius to list your hat at that time. It’s almost like looking for your wedding ensemble oh-so-many months in advance. You have to get your outfit in advance of the big day to make it perfect.

I told you we take our hats seriously. Or, maybe not …

Honestly, I start to think about Derby outfits around Christmas. Mainly because I am usually in Texas visiting my family at that time, and I know that if I buy a Derby outfit there, nobody else will have it here. We all know what a buzzkill it is to see someone with your Derby dress. And, because this is a small town, you tend to see yourself coming and going at big events such as this.

Hats are a different animal entirely. You can always spot a local during Derby because they have a good hat or fascinator, along with their spot-on outfits. Those poor tourists from out of town don’t stand a chance surrounded by the Kentuckians. You know who they are too – the ones who paid too much for their third-floor clubhouse box and are all wearing unfortunate hats — or no hats at all! Last year, our box neighbors from out of town were wearing jeans, and only one woman had some sort of adornment on her head. I won’t even qualify it as a hat. Bless their hearts!

Hats are BIG business here. Just ask some of the local milliners: Britni Knable, Kenzie Kapp, Jenny Pfanensteil or The Hat Girls. Better yet, go ask Dee’s. They make the majority of their annual income all because of the first Saturday in May.

Here I am wearing a custom hat from HeadCandi by Britni Knable. It was stunning (and heavy!).

All Louisvillians have a hat hookup, a dealer if you will. Either they know a girl, or they have an ace-in-the-hole venue. I’ll let you in on my secret … it’s Pix Shoes downtown on Preston. Yes, they are the place to get Danskos and SAS shoes for work, but they also have great hats and fascinators, all for about $50. They are all pretty plain, so you can run over to Dee’s and fancy them up if you’d like, or leave them as is.

RELATED: How to Make Your Own Derby Hat: An Easy Guide

This pic is from a freezing Oaks (how is my friend Tiffany Cardwell going sleeveless?), and it shows my favorite hat from Pix Shoes.

We all have a method to our madness. Some girls buy the hat first and then the dress. Some girls buy the dress first and then the hat. Some girls wear an old dress and get a new hat every year. Some girls spend upwards of $300, and oftentimes their hat costs more than their dress. Others spend a lot of time making the hats themselves — that, my friends, is an amazing amount of sweat equity for a head topper. But here’s the common thread: all Louisvillians try extra hard for Derby. We know that all eyes are going to be on our city, and we are camera ready.

vicki dortch derby fashions

Vicki Dortch from WLKY has her hat made by Lorie Laughead at Dee’s. I call Lorie the “Queen of Dee’s” — the woman is a magician!

I have about 10 hats that I have collected through the 20 plus years I’ve been going to Derby. I usually lay them all out on my dining room table about a week before, choose my hat and then let my friends come over to borrow the rest. They are plain and simple, but I do that on purpose. I want to wear them time and time again with a variety of dresses and colors. I have even rented a hat from Rent the Races, and that was a pretty great experience — all the excitement from having a designer hat at Derby that I could then just send right back after the big event. It’s the same concept as Rent the Runway … but with hats. Brilliant for those who cannot commit to a topper.

rent derby hat

This was my selection from Rent the Races – the firecracker fascinator with no headband, just an elastic strap.

There is a subculture of women who are amateur milliners; they revel in heading over to Dee’s, Hobby Lobby or even Michael’s and doing it themselves. Their hats look amazing, but, while there are helpers there to guide you through the process, it’s hard work. You can buy a pre-formed hat or fascinator disk and go to town designing that perfect hat for your outfit. I tried it one year and basically bought everything on aisle 14, tried to place it all on the brim while not looking like something Sanford and Son would use. After all the furrowed brows, creative roadblocks and countless hours spent, I realized I had no way to properly fasten all these items I had so carefully placed all over my hat. I put everything back and walked away. A girl has to know her limits. I’d rather try to balance the national budget than make a hat again, and girls, I don’t do math.

An Easy Guide To Making Your Own Derby Hat

Making hats and fascinators at Dee’s – with so many glue guns blazing they had to put in a power strip

After working on countless stories about hats and milliners over the years at StyleBlueprint, I vowed to get a really nice hat or fascinator last year. But I chickened out when I heard the weather report, so I borrowed a headband with a flower on it for the big day. That headband was soaking wet and frozen to my head by 5 p.m., and I was glad that I did not spend the big money for the fabulous hat. When the weather started to look grim for Derby, countless news stories were dedicated to how to save your hat. Girls walked in with their hats wrapped in plastic, holding them like a tray full of champagne. If your seats were undercover, you could do the big unveil for your hat and wear it carefully and cautiously for the rest of the day. But in some places the water was a little too dangerous, and those beautiful hats remained vacuum sealed and protected – sometimes in their own seat – for the duration of the day. Such is life in the Ohio Valley weather pattern, as we all know.

RELATED: Louisvillians Love Their … Funeral Homes

Freezing, raining and looking like the Virgin Mary last year at Oaks (note headpiece in my husband’s hands) … so much for wearing the nice hat!

This year … this is my year. I’m going big or going home – hopefully with some winnings in my appropriately sized clutch bag and clear totes.


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