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A heads-up on headgear for Kentucky Derby day

A one-of-a-kind designer hcalled 'Pool' by Jenny Pfanenstiel Couture Milliner Chicago-based Forme Millinery. | Phoby Detlef Koertge Haus Forme

A one-of-a-kind designer hat called, "Pool," by Jenny Pfanenstiel, Couture Milliner of Chicago-based Forme Millinery. | Photo by Detlef Koertge, Haus of Forme

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Updated: June 3, 2013 3:15PM



Saturday is the Kentucky Derby, a day Chicago’s well-dressed and well-meaning attempt to channel the greatest two minutes of sports into a lifetime of mint julep-fueled fashion memories. At parties, local racetracks and bars, Derby Day can be a fashion minefield as Midwest style attempts to channel Southern tradition.

We checked in with Jenny Pfanenstiel, a Bronzeville-based couture milliner who is working in Louisville creating custom Derby hats, and Chicago image consultant Barbara Glass for tips on making your local Derby duds more hit than miss.

1. Want to wear a crazy hat?
Go for it.

“I do a lot of Derby hats for people in Chicago that might be coming to Kentucky or going to Derby parties,” Pfanenstiel said. “It’s almost a reason for them to go over and beyond their comfort zone and get a bigger hat than they would normally wear, or a more flamboyant hat. ... People in Chicago have always been very outgoing with their hats. They’re always aggressive and not afraid to try new things.”

One tip? Get the hat first and then figure out the rest of your outfit.

2. A decorated headband isn’t a hat, but it’s better than nothing.

Pfanenstiel calls a feather headband (which she also makes) “playing it really safe.” But it’s better than bare.

“If you go without anything, you will stick out,” she said. “Every single person wears something.”

Glass said headbands aren’t cheating on hats.

“It’s just embellishing on a new idea, looking modern,” she said.

3. Thanks to Kate Middleton, we know what a fascinator is. Feel free to wear one.

While not the traditional big-brimmed Derby hat, a fascinator is a chic way to get in the spirit of the event.

“People actually know the word fascinator,” Pfanenstiel said. “For the Derby, people are wearing the fascinator more and more. It’s not covering up your eyes and you’re not having to take it off to watch the race. You’re not bumping into people.”

Big-brimmed or fascinator, Pfanenstiel suggests punching things up with color.

“There are definitely great colors — navy blues, emerald green, peaches,” she said.

4. Jeans might work in Chicago, not in Louisville.

“I think if you’re wearing a fascinator it could be fun with blue jeans, though the blue jeans have to be very chic-looking,” Glass said. “If you want to mix it with blue jeans, why not? We wear high heels with blue jeans and that was unheard-of at one point.”

5. Factor in the weather

Chicago springs are wet and windy. Tie that hat down, Glass said.

“We’d all like to look like Princess Catherine, but we have to deal with a lot of factors in Chicago including wind,” she said. “It’s quite fashionable to have it tied under your chin.”

Glass wears a hat constantly to shield herself from the sun. It’s a good look regardless of the occasion, she said.

“I think for particular women, with all that long hair being so popular, a hat is a beautiful accessory.”



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