Before founding Staple Design, Jeff Staple was studying communication design at Parsons School of Design, sneaking into the silkscreen lab after hours to create small batches of shirts to sell at shops in SoHo. For Staple, this wasn't about designing clothes. Instead, he wanted to find a way to growth-hack his messaging. Now, nearly two decades later, Staple is widely recognized as one of the founding fathers of streetwear. His company has produced collaborations with the likes of Cole Haan, Dr. Martens, Coca Cola and even Facebook. In the fifth and final episode of Glossy Trend Watch: Streetwear Edition, fashion reporter Danny Parisi sits down with Staple to discuss the rising popularity of the collaboration model, the difference between collabs from licensing agreements, and the way street culture is infecting society.

For heritage companies like Fila or Champion -- which have product ranges covering everything from hype sneakers to activewear -- success relies on being able to appeal to a diverse consumer base. According to Louis Colon, Fila's vp of heritage and trend, the company's history in a variety of different categories created an opportunity to authentically stretch the brand and reach a newer, younger customer. On episode four of Glossy Trend Watch: Streetwear Edition, fashion reporter Danny Parisi sits down with Colon to discuss the role of a heritage brand, the categories a brand should enter to feel authentic, and the way a brand built for tennis courts became an essential player in streetwear.