Wondering which headpiece to don on derby day? Take a cue from these hat-clad ladies.

Susan Barrett (director, World Chess Hall of Fame)

How many hats do you own?

I have no idea how many I have, but let's say it's in the three digits....

Where did you get this hat? 

I made my hat; that is, I re-appropriated a few vintage hats and other materials and created my own hat. I think I used three different hats for this one; and the flowers, fabric, etc., probably came from scraps I have. I've created a couple of dozen hats like this.

Millie Cain (VP, First State Bank)

Do you have a hat collection?

I do. I probably have about 15 at this time, and I'm always wooed into looking at hats. I'm from the era of having seen my mother get dressed in hats, gloves, clip-on earrings… so that was kind of how I was brought up.

Where did you get this hat? What made you decide to purchase it?

It was designed and custom made by Ken Meisner of Ken Meisner’s Flowers. I chose it because the coloration was beautiful; I like the translucent aspect of the fabric that was used. If I were out at a garden party, the way the sun would come through would be nice and shadyand very flattering.

Maria Clifford (former fashion executive)

What do you look for in a hat?

I usually purchase a hat to complete a specific outfit, so I start with the color and then the feel of the event I may be going to. I prefer a bright color with my dark hair; and, in the end, it is really all about how well the brim frames your face.

Why should women wear hats?

Women should wear hats because they are an additional way to express your individuality and style. They show others that you have confidence and have put effort into your appearance. Hats add polish to an outfit and recall a bygone era when women dressed like ladies.

Ann Perry (interior designer)

How many hats do you own?

I currently own five hats, donating old hats and acquiring new ones seasonally.

Where did you get this hat?

I bought a simple hat, then 'enhanced' it myself to create something a little more fun! Embellishing a hat is very easy. Find a basic hat in a style or size suitable to your face and body frame, then look at hats online to find designs which inspire you. With visions of an 'ideal hat' in mind, head to a craft or fabric store for ribbon, flowers, whimsical accoutrements and wire, which can easily be attached with simple stitches using strong thread. As you create your hat, remember the age-old adage: Less is more!

Susan Sherman (president, Susan Sherman Inc.)

What do you look for in a hat?

I look for something that bucks the trend: no bows, flowers or ribbon for me. The fascinator is sculptural and contemporary, so it felt right, as I am a huge fan of contemporary art. I tend to go large or small, nothing in-between; and I like a hat which is a bit off-kilter.

Where do you wear hats?

I don't wear hats regularly, just once a year at the Hat Luncheon to benefit Forest Park.

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