On this episode of Staying Alive, hosts Jon Gabrus and Adam Pally grab a lunchtime sit-down with fashion writer/editor Jake Woolf (GQ, Robb Report) to talk about how what you wear figures into your mental health, compare notes on their high school styles, therapy regimens, feeding the algorithm, and wonder about moving from critic to designer. Plus: Gabrus and Pally talk about their teenage sketch groups, and which LA canyon has the most cougars (no, not that kind).

Follow Jake @jakewoolf on Insta

Check out Jake’s Substack!

Full video episodes available HERE.

Check out Staying Alive merch at siriusxmstore.com/stayingalive

This episode was recorded April 2, 2025 at SiriusXM studios in New York City

Special thanks to Jared O’Connell and Casey Holford

Staying Alive is produced by Devon Torrey Bryant and Anne Harris

Engineered and edited by Devon Torrey Bryant, who also wrote the music

Associate producer and video editor is Maddie McCann

Executive produced by Jon Gabrus, Adam Pally, Sean Hayes, Will Arnett, Jason Bateman, Bernie Kaminski, and Rich Korson

Keywords for this episode: MRI, Ike Barinholtz, Gianna Michaels, OnlyFans, Apple Watches, Superman, Airwalks, Rusty, Quiksilver, Doc Martens, GQ, ESPN Zone, Jimmy Butler, grey rollneck J Crew sweater, The Morning Show, Long Island Little League, Allen Iverson, Joe Namath, DJ Cousin Ben, surfwear, Substack, Ven.Space, The Row, Aaron Levine

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.