Reginald Sherard is a modern day hat maker and hat designer

By Staff

Tell how and why you became an entrepreneur.

I became an entrepreneur because after working for different companies and organizations I would feel used and and unfulfilled. Something in me said if I’m working this hard and putting in long hours for someone else’s business, I can do the same for my own business. So after owning a security company for 10 years and then a cyber safety consulting company for 6 years, I landed at hat making because at my core I’m a creative. Hat making allows me to stay inspired and motivates my creativity because with hats I’m creating something different every time.

I also wanted to be able to not have to ask someone if i can take time off to be with my family, which is important to me. 

Tell us about your company and product.

Nathan Mason Hats specializes in making custom hand made and hand crafted hats using rabbit and beaver furfelt. We also make straw hats as well. We’re located in Huntsville, Alabama and we’re the only custom hat shop in the whole state of Alabama. 

What has been the biggest challenge thus far?

Wow. There are many, but some of the top ones is opening a business in a city I don’t actually live in. There are different expectations and regulations that you have to be aware of before deciding where you want to open a business. I only wanted to do a 30 day pop-up shop but things were going so well that 30 days went to 60 days. 60 went to 90 days. 90 days went to me opening a store.

Another big challenge was being away from my family while opening up a business in a different city as I technically still reside in Washington, DC but Huntsville is home.

Tell us about your visit with the people from Uncle Nearest.

I have been inspired by the Uncle Nearest story and the history of it since day. CEO Fawn Weaver is an amazing woman who took something that she had no previous experience in and made it the #1 brand it is today. I believe her passion for the mission of telling the story of Uncle Nearest is what got her there. It reminded me of myself and how I had no prior hat making experience but my passion and my vision to create custom hats that tell a story of the person wearing them inspired me to master my craft and become a master hatter. So I had the idea to duplicate the hat of George Green, the son of Nearest Green, because I believe the hat told a story. There’s a photo of him seated with Jack Daniel and some other men and he’s rocking a hat. He’s not just wearing the hat but rocking it! It’s tilted to the side and there are markings on it that give it so much character. Him being the only black man in the photo stood out to most people but for me, it was him being the only black man in the photo and the only one with his hat tilted to the side. Although the person in the photo wasn’t Nearest Green but his son, we can say that the hat was passed on to him because that was something that was common in those times. Fathers would give their sons their previously worn hats or they would receive them after the father passed away. Every hat really does have a story, especially in those times where men and women didn’t leave the house without wearing one. 

Fawn Weaver, was on a “CEO Thank You Tour” and Huntsville was one of her stops. The local beverage representative for Uncle Nearest was one of my first customers when we started our pop-up shop in Huntsville. I reached out to him and told him about my idea and after a few calls they added us to her stop, which was such an honor. I had no idea that Victoria Butler, the great great grand daughter of uncle nearest, was going to be accompanying them. She was so moved by it that she cried. I was not expecting that type of response at all so I too got a little teary eyed realizing that I created something reminded her of her history. Fawn was so in awe of the craftsmanship and how I was able to make the hat look exactly like the hat in the photo. So much so that they plan to put it in the welcome center at the distillery in Shelbyville, Tennessee. 

What is one of your most special moments as an entrepreneur?

Hearing my children talk about how their Dad owns a hat store in Huntsville, Alabama. For his show and tell at school my son showed his class an article of me in the Associated Press online and he told them about me being a hat maker and someone recorded him. To see him be so proud and excited to speak about me moved me to tears. Especially with him being the “Mason” of Nathan Mason Hats nd the youngest of my threw sons who I name the business after, I want him to have a since of pride when telling the story. 

Where would you like to see your company in the next five years?

I’d like to have at least three more boutique locations open in three different cities and full administrative and operations staff, and more partnerships/collaborations with brands. I plan on offering hat making classes and hat designing pop-up tours for those that desire to learn the art of hat making and it’s rich history of craftsmanship. I also plan to add, ready to wear hats, clothing, men’s grooming products, cigars and a whisky to the brand. I always tell people it’s bigger than just hat making. I will be a lifestyle brand in 5 years. Hat making and hats are a huge part of history and they have they’re own culture and following and my goal is to bring that back to the forefront so I have no doubt it will happen.


After searching for hats to fit his head, style and personality he sought to understand how hats were made. He sought a millinery in Washington, DC who showed him in one session how hats are made. Determined to learn the art of hat making, he began to research online and studied more about the craftsmanship and its culture.

In his research, he discovered the rich history of creatives and artisans known as milliners, a person who makes and designs hats. His love for hats turned into a passion where he then turned it into a business. Being a serial entrepreneur, he realized that he could make a living by doing something he loved. He named his business Nathan Mason Hats, after the names of his sons, Nathaniel, Jordan and RJ Mason.

He wanted to create something that he could pass onto his children if they so choose to become hat makers. Reginald describes his hat making style as a combination of “modern and classic” as he uses both vintage and 3D printed tools to bring the imagination of the customer to life.

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