During the COVID-19 pandemic, Whitney Port decided to rewatch "The Hills" and "The City" and had the idea to film her and her husband Tim Rosenmann's reactions for her YouTube channel (via Feeling The Vibe Magazine). During their rewatch, the couple provided commentary on everything from Port's early '00s fashion choices to her dating life.

Over a decade removed from her reality show days, Port was able to laugh at her 20-something self. "I never really loved being in front of the camera. It wasn't something that I fully felt natural doing ... It's really not until I started filming these videos with [Rosenmann] that I gained my comfort and I felt like I could really be myself," Port told Vogue in 2021.

Port's first rewatch of "The City" got over 400,000 views, while her reunion with her "The Hills" co-star Lauren Conrad racked up more than 800,000 views. The reality star's videos are helped along by Rosenmann, who was a producer for "The City" and gives viewers background information on post-production secrets, per InStyle. While Port's YouTube presence is growing, she hasn't forgotten her fashion roots and created a line that helped her through a difficult time.