Reginald Sherard aka One Man Many Hats A Modern Day Hat Maker And Designer


By Taroue Brooks

What inspired you to become an entrepreneur? 

The idea of ownership was always something I desired at an early age. I would see things and say to myself “I could own that, or why don’t “we” own that.” As I got older, I saw my aunt own a day care center, my sister owns an accounting company, and I was hired as Operations Manager by a black man in Oklahoma who owned a security company. Working closely with him encouraged me, actually all of them, proved to me that I could become a business owner. I began to pursue my dream of becoming an entrepreneur by owning a private security company and later a cyber safety consulting company. Once I experienced working for myself and being responsible for giving other people opportunities, I never wanted to go back to working for anyone else. As a matter of fact, I tried several times, but I could not forget the vision that was inside of me. I always knew that earning money for someone else was not the life I desired. I wanted to show my children they could be business owners and not have to trade time for money. 

Tell us about your company and product. 

I started making custom hats a few years ago for myself because I could not find hats that matched my style and personality. Once I started doing that people would inquire as to where I purchased my hats, and when I told them I made it myself they would ask me to make one for them. I realized that I could turn the art of hat making into a business, in addition to passing the trade on to my children whom I love dearly. I searched for a milliner to mentor me and found one in the area and worked with him for one class and he never answered after that so I did extensive research on the history and craftsmanship of hat making myself.  After a few years of working to master my skills and word of mouth advertising, I launched Nathan Mason Hats, named after my three sons. Currently, we offer custom made hats and, in the future, our goal is to have ready to wear hats, a clothing line, and a grooming brand called Tilted Brim (TM).  We use rabbit, beaver, and a rabbit and beaver mix fur felt only, which are all sourced in the USA.   

In such a competitive market, how will your product/company stand out? 

There may be many hat designers out there, especially since the pandemic and people are at home looking for ways to spend their time and be creative. I have respect for those people, but what sets my company apart is that I am a “hat maker” AND a designer. A milliner. My hats are handmade, hand crafted, and inspired by the customer’s input, and for those that lack the gift of being creative my team and I can assist with ideas. Again, I started making hats to fit my versatile style and personality, so I can make a hat for every occasion and just about every style. Whether it’s for the everyday working class, the Sunday service goer, the hoody rocker or for the ranch worker I can get anyone hatted. 

Tell us about your pop up store in Huntsville, AL? 

I’ll be doing a popup shop in the Parkway Place Mall in Huntsville, AL September 6 – October 3, where I will be showcasing custom hats, offering custom hat consultations and fittings, and doing hat making demonstrations so that mall shoppers can get a visual of how custom hats are made. Patrons will also be able to choose options for their custom hat on the spot. It will be like the Chipotle of hat making. Pick your base, add your ingredients and pay at the register!

 What does success look like to you?  

Success means reaching a goal, accomplishing a task, bringing satisfaction to customers and them wearing a product that was created with them in mind. Essentially, success is being intentional in accomplishing the desired goal. Beyond that, the definition of success is personal. 

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

I would like to see the systems that are being put in place now, working so that customers can have their hat to rock in a timely fashion by utilizing the benefits of technology. I’d also like to do hat making tours where people will have the opportunity to be taught the culture of hat making; making and designing their hat in person, will give them that added personal touch. And, of course growth of the business is always key, opening boutique stores in different states as well as abroad.  

Find Out More

Follow on Facebook




Reginald Sherard aka One Man Many Hats is a modern day hat maker and hat designer. After searching for hats that fit his style and personality he sought to understand how hats were made. 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 that he turned into a business. Being a serial entrepreneur, he realized that he could make a living off of doing something he loved so he named it Nathan Mason Hats, after the names of his sons. Reginald describes his 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.