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About Us

Trunk Club was started to solve a simple problem – shopping for clothes in stores or online just doesn’t work for most guys. It’s overwhelming, inconvenient, and takes way too much time. With Trunk Club, guys discover awesome clothes that are perfect for them without ever having to go shopping. We combine top brands, expert service, and unparalleled convenience to deliver a highly personalized experience that helps guys look their best and saves them time.

We scour the planet for the very best in men’s apparel and curate an ever-evolving assortment of pieces from our favorite designers. With the best inventory anywhere as our point of departure, a Stylist on our team hand-selects a trunk of items based on each customer’s needs and tastes. They keep what they love and send the rest right back to us, at no cost to them.

Our team is based in Chicago, IL and has grown from four to over 300 since starting out in December 2009. We are backed by awesome investors, including US Venture Partners, Greycroft Partners, Anthos Capital, and Apex Ventures.

Management Profile

Brian Spaly


Brian is excited to help change the way men shop. Now leading his second venture-backed fashion start-up, Brian is focused on making it incredibly easy for guys to discover awesome clothing without the hassles of the traditional shopping experience. Prior to leading Trunk Club, Brian founded Bonobos, a men’s clothing company that is famous for the best fitting pants on earth. Under the leadership of Brian and his co-founder Andy, Bonobos was named one of the fifty hottest brands in America by AdAge in 2009. Brian holds an MBA from Stanford and a BA from Princeton. With Brian, you don’t have to call it Mexican food. You can just call it “food”.

Rob Chesney


As a former Vice President at eBay and Executive in Residence at Greylock Partners, Rob has deep e-commerce expertise and experience leading new businesses through periods of hyper-growth. As COO, Rob plays a central role in the general management of Trunk Club, overseeing customer acquisition, leading innovation of the technology platform and managing the build-out of the company’s operations. Rob holds an MBA from Kellogg and and a BA from McGill University. He looks forward to taking his son to a Cubs World Series game… before his son grows up.

Kevin Price


Kevin heads up the financial operations of Trunk Club. Prior to Trunk Club, Kevin worked in private equity at American Capital, focusing on pre-investment financial & accounting due diligence, portfolio company valuations, and portfolio monitoring. Prior to American Capital, Kevin worked in the financial advisory services practice at Deloitte & Touche. Kevin earned a BS in accounting from University of Illinois Urbana Champaign. Kevin knows Judo.

John Tucker

VP of Member Experience

John is focused on service, design, and technology at Trunk Club, ensuring everything runs smoothly behind the scenes. Prior to Trunk Club he was a Fellow at Acumen Fund, a design project lead at IDEO, and a technology program manager at Sapient. He holds a BA in Economics and Physics from Bates College. Outside of The Club, John is most likely to be spotted in the dark underbelly of the Chicago table tennis world looking for an even match.

Jason Smith

VP of Merchandising

Jason leads our merchandise product strategy. His mission is­ to teach every guy how powerful a blazer can truly be. Jason brings over seven years of direct experience to the game from sales and management roles in the fashion accessories industry with Allegro Manufacturing. Jason is a veteran of start-up environments having held business development and corporate planning roles at eToys and LivePlanet/Project Greenlight. He is also a survivor of corporate stints with General Electric and an ex-management consultant. He has Benjamin Button’s disease.

Jon Armitage

VP of Marketing

Jon manages all things marketing. With a background in eCommerce as a Vice President at Expedia helping drive the Hotels.com brand, and earlier experience at Google, Jon brings knowledge from a number of years in marketing efforts at high growth, online businesses. In this role, Jon is responsible for customer acquisition, retention, and engagement efforts—as well as developing the Trunk Club brand. Jon attended King’s College London back in his native England and outside of his pursuit to bring the Trunk Club experience to as many guys as possible, he is likely to be found at Chicago’s sporting venues following his adopted city's many teams.