How these MIT founders are designing functional fashion for the future of work

Jess Li
Rough Draft Ventures
3 min readJul 31, 2019

A recent national survey by fashion platform Lyst found that over the past decade, 80% of Americans have experienced a shift in their workplaces toward more casual work culture. Increased connectivity has enabled more flexible work arrangements and has contributed to a broader definition of what constitutes the workplace. The traditional office, replete with cubicles and stringent dress codes, is not the only place that professional work gets done, nor is 9-to-5 the only viable working window. Instead, with the greater technological ability to work remotely, people are increasingly working from homes, cafes, and co-working spaces during whatever hours best fit their multifaceted schedules.

While corporate changes have taken place to support the movement toward greater work flexibility, the fashion industry has failed to keep up. Today’s modern workers want comfort, function, and style baked into every product they purchase so they can achieve their personal and professional goals more practically. Their lifestyles demand they be adaptable to any environment — and look good doing it. Dynamic schedules require outfits that flow seamlessly between breakfast with a client, lunch with friends, and dinner with the in-laws. While companies like Everlane, Stone Island, and Entireworld address these concerns for apparel, the need for stylish all-weather products like boots, coats, and bags is still at an all-time high.

Season Three, an apparel company founded by MIT Sloan MBA students Adam Klein ’19 and Jared Johnson ’20, is creating products that address these consumer pain points. Their first product is a simple, sleek, and rugged all-weather boot that is handmade in Italy with a full merino wool lining. Comfortable to wear all day long, these boots combine seemingly contradictory features to cater to the needs of the WeWork generation.

Adam and Jared were inspired to found Season Three amidst a cold, rainy Boston day. Adam was at a loss for fashionable footwear that would shield him from the awful weather. He decided to go barefoot through the streets instead of setting for ugly utilitarian boots or ruining his favorite sneakers. Finding Adam in this state, Jared took Adam under his wing. Together, they commiserated over the lack of footwear options available. After speaking with their friends and classmates, the two realized this footwear challenge was a common challenge for consumers in urban centers. They sought to solve this problem through well-made staples at Season Three.

Adam comes from a strong finance, law, and startup background. Adam holds degrees in finance, law, and business from NYU Stern, Fordham Law, and MIT. He has spent time in investment banking, US Grid Company, and Menlo Security.

Jared has a strong background in design and finance. Jared has degrees from Purdue, the Flatiron School, Harvard, and MIT in management, software engineering, policy, and business. He has spent time at JP Morgan Asset Management, IDEO CoLab, and ZX Ventures.

Both Adam and Jared are deeply familiar with the neglected market they seek to fill through Season Three. They bring years of experience in a wide range of core disciplines and provide a fresh perspective to their disruptive D2C brand. “We wanted to create a launching pad, where we could make stylish products that maintain the utility of a traditional boot, but are designed for the needs of the urban warrior. On a winter day, Adam and I want to go from workout class to school meetings to drinks all in the same pair of shoes; we want our friends to be able to do the same. We are two people with a passion for well-made, comfortable, and stylish products,” said Jared.

Rough Draft Ventures is excited to back Season Three as they build an accessible, functional, and aspirational brand for the workforce and society of tomorrow.

Season Three preorders begin in September and the company has opened the waitlist for the product here. They share incredible content on the future of fashion, workplaces, and society through their Instagram and blog.

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