Between 1989 and 1991, Gary navigated harsh winters and muggy summers as a bicycle messenger in Boston. This experience taught him exactly what works in a bag, and what fails under pressure.

Gary founded WaterField Designs with a bold first product: the Cargo Laptop Bag. Combining the practicality of a briefcase with the cool factor of a bike messenger bag, it struck a chord with creatives, entrepreneurs, and early tech pioneers.

The unveiling of Apple’s titanium PowerBook in 2001 became a turning point for WaterField Designs. Gary doubled down on Apple products, creating a custom-fit sleeve tailored to the iconic laptop.

Apple’s 2001 launch of the original 5GB iPod—with its iconic click wheel—inspired our first custom-fit cases. As the iPod evolved and the iPhone arrived in 2007, WaterField Designs expanded into cases for every new generation of Apple devices.

2014 marked a major evolution for WaterField Designs: moving beyond cases into backpacks, duffels, and briefcases with built-in laptop protection. Leading the charge was the Staad Backpack, our first-ever backpack design.

In 2017, WaterField Designs introduced its Community Design concept, inviting customers to help shape new products. The result was the Switch CitySlicker, a refined gaming case that marked the company’s entry into the gaming market.

See other community designs here.

As COVID lockdowns emptied offices in 2020, demand for work bags was greatly reduced. WaterField Designs responded by branching into aprons and dog accessories, keeping its craftspeople employed through the uncertainty.

Apple’s AirPods Max debuted in December 2020 with a minimalist case that left many users wanting more. WaterField Designs stepped in with a superior alternative that generated enough demand to keep the company running at full capacity for six months.

WaterField Designs closed out 2025 with six Wirecutter and New York Times “Best Of” awards, highlighting customer favorites like the Air Porter Carry-On, Executive Leather Messenger, and Packable Backpack.