The most fashionable Kentucky Derby hats come from Oak Cliff

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Boutique owner Cassie MacGregor’s busiest season begins at the end of January.

That’s when clients from Highland Park and other tony addresses start trickling into her petite salon upstairs from Bolsa.

MacGregor, whose House of MacGregor millinery opened around the same time as Bolsa in 2008, will make 150 hats by the time the thoroughbreds Run for the Roses May 5.

MacGregor doesn’t work with an assistant; she designs and creates every one by hand from start to finish.

She’ll make adjustments and final touches up until the Friday before the derby, having spent three to five hours one-on-one with each customer throughout the process. 

“I have to make sure that everyone has a different hat, that they’re all in unique styles,” she says. “It’s like having brides.”

Her hat ladies (if we may generalize; some are gents) bring their derby outfits to the studio and try them on for consultations. It could take close to an hour just to choose the materials MacGregor will use.

Some clients also attend Oaks Day, when the mares run on the Friday before, so those hat ladies and gents require two custom pieces of headwear.

Each handmade hat costs between $375-$475. Fascinators cost $175-$300.

By the day of the derby, MacGregor has earned half her yearly salary, but it’s so much work that she’s never been able to have a derby party of her own.

She usually goes down to Bolsa for a mint julep.

One year, a man also watching the Kentucky Derby in the bar at Bolsa asked MacGregor if she would give him and his wife a tour of her studio. 

She declined: “I was just so exhausted, and I was like, ‘I’m sorry, it’s a mess up there, and I just can’t right now.’ ”

“Do you know who that was?” a Bolsa employee asked later. 

It was Tim Delaughter.

“I was like, ‘oh, great,’ ” she says. “I could’ve been designing hats for the Polyphonic Spree. That would’ve been a lot of hats.”

She always takes the second week of May off to decompress.

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“My customer service skills are shot,” she says. “This is so creative, and I love it, but I could never sustain it for a whole year.”

The rest of the time, MacGregor creates ready to wear and custom hats that cost $135-$175 for hemp or straw and more for felt. She also sells a limited number of hats from other independent milliners, and she holds occasional trunk shows for other designers.

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