Catching Up with David Hamilton, Owner of Hamilton Shirts

David Hamilton of Hamilton Shirts inherited a clothing company from his family—When he took on the business with his sister, the enormity of preserving the family legacy weighed upon him. But David and his sister Kelly hardly let those fears stop them.

Hamilton Shirts has been in business since 1883, begun by the Hamilton siblings’ great-grandfather. For four generations, the Hamilton family has created custom shirting made from the highest quality cotton, and they offer a truly bespoke shirt. 

Preserving the family legacy meant making a huge career move for David, but once he made the leap, he hasn’t looked back. Hamilton Shirts is currently the oldest business in Houston, Texas. David and Kelly are also Cotton Makers, a group of craftsmen and women who work with cotton and whose professional risks have yielded some amazing success stories. We caught up with David for a chat about how he faced his fears and turned a family business into a rewarding career.

Watch the Hamilton Shirts Cotton Makers video, read about David’s journey, and shop the collection below!

What was your biggest fear when starting this venture?  

Fashion is an industry that is always changing and very few businesses are able to remain relevant over long periods of time. Our greatest fear was that we wouldn't be able to continue the success of previous generations running the shirt factory. Could we remain true to the brand while at the same time evolving?

Was there a specific moment or turning point when you knew this was what you wanted to do for a living?  

Growing up I was not very interested in the family business and perhaps took it for granted. After graduating college I worked in finance and found the work personally unsatisfying. At that point I started to realize how special Hamilton Shirts was. It had an amazing product, heritage and team. I was nervous about leaving finance behind, but knew almost immediately after making the transition that it was the right move.

What does “creation” mean to you?  

I think it takes many forms for different people or organizations. For us, it's about working together over a long period of time to create something special. Continually looking for some small, incremental improvement that we can make. That's the kind of dedication it takes to be truly best in class.

Could we remain true to the brand while at the same time evolving?

What’s your ideal comfortable moment?  

Being fully present and focused. Disconnected from all types of distractions.    

What advice would you give to someone looking to start their own business?  

Follow your passion. Most businesses aren't about great ideas but great execution. It takes about 10,000 hours until you're really good at something.

“Stepping out of your comfort zone” is a frequently-used phrase. What does it mean to you?  

Being open to new ideas or experiences. Pushing ourselves to the edge of our abilities because that's where growth happens.  

What was your proudest moment as a creator?  

Building a team that does better work than I do. 

Pushing ourselves to the edge of our abilities [is] where growth happens.

Clearly, resting on one’s laurels isn’t exactly in David’s vocabulary. Rather, his source of comfort derives from a job well done, finding an outlet in creativity and hard work, and building a business rooted in tradition, with an eye trained on the future.

You can shop ready-made shirts by Hamilton Shirts below and in Shop Cotton. Follow Hamilton Shirts on Instagram.

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