
GLOUCESTER — Michael Bradley, a 25-year-old from Gloucester, noticed many of his hobbies and passions were being pushed aside by work.
Wanting to get back to the lifestyle that he enjoyed, Bradley founded Chesapeake Clothing Company in early 2024.
“Our philosophy is to spread the love, joy, and relaxation that is associated with living a coastal lifestyle. Through our tagline, “Live Free. Live Coastal,” we aim to remind customers why we all fell in love with being on or near the water,” Bradley said.
Bradley grew up on the water himself, and enjoys fishing, crabbing, and going for boat rides. He is immersed in the coastal lifestyle and wanted to create products that could show the same sense of pride that he has about living on the water.
Chesapeake Clothing Company offers a wide variety of apparel, including t-shirts, sweatshirts, hoodies, hats, quarter zips, and children’s clothing. All clothes are themed around the Chesapeake Bay.
“Our goal is to be known for providing various wholesome and family-oriented apparel items that illicit a sense of freedom and joy for our customers by spreading seaside style,” Bradley said.
While he has no brick-and-mortar storefront, Bradley aims to make the website easy to use. Customers can shop the online storefront and easily ship items directly to their location.
“What sets us apart from others is our desire to remain simplistic so that customers are reminded of just how simple, yet joyful life can be when you dive fully in to the coastal lifestyle.
The team at Chesapeake Clothing Company also offers custom designs. While custom designs are available for a small upcharge, Bradley is happy to speak with any customer who wants to create something personal.

For Bradley, operating in the Historic Triangle is exciting.
“Our favorite part of being located in the Historic Triangle is the breadth of individuals and unique backgrounds present, particularly when it comes to those engaging in activities on the water. The Historic Triangle presents a unique melting pot of coastal individuals which ranges everywhere from hardworking and dedicated watermen to weekend sailors and everything in between,” Bradley said.
Bradley hopes to open permanent locations in the future.
“As an e-commerce business, we operate 24/7 to ensure our customers have the ability to purchase the products they want, when they want. We hope to continue to grow and strategically open and operate brick-and-mortar locations in areas that best serve our customer bases,” Bradley says.
Chesapeake Clothing Company can be found online, on Facebook, and Instagram. To place a custom order, email support@chesapeakeclothing.com.
Community Business is a feature series that showcases locally-owned business establishments in the Historic Triangle. If you would like to submit a business to be featured, please send an email to info@wydaily.com.