Why Men Dress Like Slobs | O. W. Root

In this episode, Aaron welcomes men’s style influencer O.W. Root for a deep dive into the dramatic decline of men's dress over the past 30 years. From the universal suit-wearing era of the 1990s to today's pajama pants in public, they explore how tech culture, Silicon Valley, and the shift to digital life contributed to the rise of "slob culture." Root shares why classic menswear is fun, dignified, and accessible—even on a budget via eBay thrifts—and offers practical advice for any man wanting to dress better without looking out of place.

CHAPTERS
(00:00 - Introduction)
(00:55 - How Men's Dress Has Changed in the Last 30 Years)
(02:53 - What Caused the Slide Toward Informality?)
(05:07 - The Dot-Com Era and Tech's Role in Killing the Suit)
(08:24 - Digital Life vs. Real World: Why Physical Appearance Declined)
(11:55 - The Great Male Renunciation and the Suit as Uniform)
(16:49 - Why Politicians and Media Now Dress So Boringly)
(18:20 - Classic Style Is Fun: Patterns, Colors, and Joy in Dressing)
(22:52 - Practical Implications: Manners, Dignity, and Arrested Development)
(30:20 - How O.W. Root Got Into Classic Menswear)
(31:57 - Learning Menswear in the Internet Era (Ask Andy, Style Forum))
(34:05 - How to Start Dressing Better Without Looking Like a Freak)
(39:34 - eBay Thrifts, Affordable Classics, and Realistic Advice)
(44:32 - Final Thoughts: Dress Better for More Enjoyment in Life)

O. W. ROOT LINKS:
🐦 Twitter/X: https://x.com/owroot
🌐 The Fitting Room: https://necktiesalvage.substack.com/
🌐 Michigan Enjoyer: https://enjoyer.com/

CONNECT & FOLLOW AARON RENN:
🐦 Twitter/X: https://x.com/aaron_renn
🌐 Newsletter - In-depth cultural analysis: https://www.aaronrenn.com/