Milliner Cassandra MacGregor is helping to build a worldwide hatmaking community from her north Texas studio.

For 20 years, MacGregor has been dressing her clients in only the finest handmade custom hats. But her career in the millinery business first started with failure elsewhere.

As MacGregor tells it, she cycled through plenty of other options — none of which clicked. “I have definitely dabbled in making a lot of different things and was not good at any of them,” she says.

Then, in 2002, while taking evening classes at the Fashion Institute of Technology in New York, she tried making hats; it was the fit she was looking for.

“I stumbled into hats and fell in love with it,” MacGregor says. “The reason I’m still in love with hatmaking after 20 years is there’s always something new to learn. It never gets stale.”

MacGregor studied and perfected traditional millinery techniques the old-fashioned way: hustling in New York from one gig to the next. Over the subsequent five years, she worked with theatrical milliners on Broadway, fashion show hat suppliers, and couturiers throughout the city — cutting her teeth one custom hat at a time.

“It was somewhat of a small hatmaking group in New York,” MacGregor explains. “With the experience I had from the Fashion Institute, it was really easy to reach out to the different hatmakers in the city and get your foot in the door. Hatmakers are also extremely friendly. When you make a hat, it’s extremely individual to the person making it; so, I’ve never felt competition with other makers.”

Upon moving back to her hometown of Dallas in 2008, MacGregor — armed with Big City experience and a trove of concepts to match — opened her custom hat shop, The House of MacGregor. Located in the ever-burgeoning Bishop Arts District, The House of MacGregor has excelled as one of the premier spots in the city for fedoras, Kentucky Derby hats, wedding hats, and seasonal headwear.

MacGregor’s custom hatmaking mantra is simple: match the right hat to the right face. Every piece is bespoke to the client; every piece has a life of its own.

“I think I’m really good at meeting with a client and figuring out what hat they’re looking for, what kind of hat will feel like them,” MacGregor says. “Instead of making a hat that’s amazing and then trying to put it on someone’s head, I try to channel the person and figure out what’s useful to them, what they’re looking for, and try to turn that into the hat.”

MacGregor’s light inventory of furs, feathers, straws, and other materials ensures a careful curation of stock items as well as an avoidance of material degradation due to time. In the summer, fall, and winter months, her business is comprised of about 60 percent inventory and 40 percent custom orders. During the spring, ahead of the Kentucky Derby, it inverts to roughly 70 to 80 percent custom orders and 30 to 20 percent inventory.

As a result of the pandemic, MacGregor moved from a former automobile shop in Oak Cliff to a detached garage behind her house. Though small, the space is well-suited for her needs. Typical days involve stock item upkeep, custom orders, and exploring new techniques.

MacGregor’s hatmaking is mostly devoid of automation and groups her various stages of production. In the evening, she might begin working with materials and let them dry overnight on a wooden block. The following day, she will wire and trim each hat out.

Photos courtesy The House of MacGregor

In her studio, she has a steam iron, a couple of heated hat stretchers, a sewing machine, and a handheld steamer, as well a large collection of vintage hat molds, which are used to shape the crown or brim.

As part of a niche industry, MacGregor must be quick on her feet when supply sources unexpectedly dry up. The pandemic has simultaneously made securing suppliers both easier and more difficult — depending on the particular problem being addressed.

“As a result of the last few years, suppliers have had to put all their offerings online, so I feel like I have plenty more options than I used to,” MacGregor continues. “There’s a couple of great suppliers in England for straws and feathers, especially during the racing season. Fifteen years ago, a lot of our suppliers were going out of business because everyone was keeping it a secret who they were getting their supplies from. A lot of the hatmakers in New York formed a hat guild. Now, everyone meets once a month, and we share our suppliers and our problem-solving. It’s been a great resource.”

Challenges: MacGregor’s biggest challenge today is finding Panama straw — but it isn’t for the most common reasons heard from pandemic-era manufacturers.

“The Panama straws we use for hats — the people who weave them, the people that do the more complicated weavings — they’re passing away, and the younger generation isn’t interested in doing the weaving,” MacGregor says. “It isn’t a very high-paying job. As a result, it’s been a challenge to get those supplies in.”

Opportunities: Though she may not automate her process, technology is going to play a large role in MacGregor’s business — namely, how she builds her hatmaking community.

“I’m part of a guild with American hatmakers that meets once a month to share ideas and further spread hatmaking across the country,” she explains. “That community has also brought me into contact with international hatmakers; as a result, there have been a lot of Zoom classes and new technologies.”

She adds, “I’ve been able to learn so many new techniques, and I’ve been able to connect with and make friends with hatmakers all over the world; it’s really cool. The experience really elevates what I’m doing. It changes what my ideas are, and it makes me feel like I’m a part of something that’s bigger than where I’m sitting in Dallas.”

Needs: In many ways, 2022 has brought good fortune to hatmakers: custom hats are back in style. But MacGregor doesn’t produce quite the style that is most sought after in the wave of popularity.

“There’s definitely been a resurgence in hats recently, which is great,” she continues. “The more hats people are wearing, the more people that are buying hats. But it’s been slightly challenging to distinguish the hat that I make from the flat-brimmed western hat that’s more common now.”

Luckily, MacGregor can clearly state what the steps are in getting where she needs to be.

“I’ve realized my niche with the racing hats, now that racing season is coming back again, is a niche that really benefits from my 20 years of experience,” she says. “I need to move my business more into that style of hat.”

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