Derby Darling

Once a year, women don their most fabulous headwear for a day filled with old-fashioned tradition and Southern charm that could only happen in Kentucky. Churchill Downs welcomes visitors from across the nation and the world to experience the rich tradition of horse racing during their annual Kentucky Derby. From horses to mint juleps, the experience has an Old South swagger that can’t be topped, but the experience isn’t complete without what most consider the crowning jewel (and most famous element) of the event -- a one-of-a-kind, over-the-top hat!

For those of us preparing to attend the event or even just hosting a party at home, I’ve found one of the most incredible milliners (hat maker) right here in North Texas. Cassandra MacGregor is a custom hat maker who specialized in exquisite and spectacular headwear just for the occasion. I sat down with the designer to find out a little more about her approach to one of the country’s most classic fashions.

Q: What is House of MacGregor?
A: We are a custom hat shop located in the Bishop Art's District in Dallas.

Q: How did you learn the craft of millinery?
A: I lived in New York for 10 years and took hat classes for fun at FIT. Two years in I quit my day job and worked for a bunch of hat makers around the city.

Q: What do you love about creating Kentucky Derby style hats?
A: Meeting the customers! Most of what we do for the derby, we create with our clients to match their outfits. It is so fun to see what comes out of our collaborations.

Q: What is the most important element or aspect of a hat perfect for the Derby?
A: The perfect derby hat is one you feel comfortable wearing. You are going to be in it all day, and it is all for fun. Pick something that feels great on.

Q: How can people purchase your designs?
A: Give us a call or visit the studio above Bolsa at 614 W. Davis St. in Dallas.

To learn more about House of MacGregor,
Looking for a fun Kentucky Derby outing this weekend? Head out to the free horse show at Black Star Sport Horses. The farm is hosting an array of family fun activities including a Kentucky Derby Hat Contest! For more info visit:

Photography features all custom made hats from House of MacGregor
Styling by Holland Sanders – see more styling work on Instagram @hauteholland

Special thanks to Black Star Sport Horses for their beautiful setting.

Models: Sara Sasso, Sophie Wolf, and Peyton DeMarais
Horse: Wendy (Special thanks to her owner Katherine Rose Watson)