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/

In this episode, Aaron welcomes real estate developer Bobby Fijan to discuss one of the most overlooked crises in American urban life: the dramatic decline of children in major cities. Once filled with kids playing in the streets, neighborhoods in New York, San Francisco, Chicago, and beyond are now increasingly childless. Bobby and Aaron explore the causes—from Richard Florida’s influential “creative class” vision that reshaped city priorities, to financial incentives driving developers to build studios and one-bedrooms instead of family-sized apartments, to skyrocketing private-school costs and the loss of family-friendly infrastructure.They also examine why this matters: cities are engines of opportunity and culture, but forcing ambitious young people to choose between career growth and starting a family is a societal failure.

Bobby shares his vision for “baby maybe” housing, practical ways to make cities welcoming for young families again, and why a biblical image of elderly people watching children play in the streets should inspire modern urban planning. The conversation ends with a provocative look at how cities have become extraordinarily dog-friendly—at the expense of being kid-friendly.If you care about the future of America’s greatest cities, this is a must-listen.

CHAPTERS
(00:00 - Intro & Welcome Bobby Fijan)
(00:55 - The Collapse of Children in Big Cities)
(03:17 - Why Kids Disappear After Age 5 (And Now Even Younger))
(04:31 - Richard Florida and the Rise of the Creative Class)
(07:13 - How Cities Catered to Young Singles—and Forgot Families)
(10:55 - The Insane Cost of Private Schools in Cities)
(12:47 - Decline of Catholic/Parochial Schools)
(14:22 - Why Childless Cities Matter)
(17:48 - Economic & Cultural Hubs Need Families Too)
(19:45 - Texas Cities vs. Legacy East Coast Cities)
(23:35 - Why We Keep Building Studios & One-Bedrooms)
(26:23 - Financialization of Housing & Developer Incentives)
(28:28 - Introducing “Baby Maybe” Housing)
(31:29 - How to Fix the System (Fair Housing, Subsidies, Vision))
(36:36 - Dogs, Kids, and the Future of Urban Life)
(46:47 - Closing Thoughts)

BOBBY FIJAN LINKS:
🐦 Twitter/X: https://x.com/bobbyfijan

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

MENTIONED IN THIS EPISODE:
📖 Richard Florida: The Rise of the Creative Class: https://www.amazon.com/Rise-Creative-Class-Richard-Florida-ebook/dp/B07M77X5ZQ/?&_encoding=UTF8&tag=theurban-20

A special Christmastime podcast reflecting on some of the guests I've hosted this year, along with a special fundraising appeal during my limited time only discount window.

Through December 12, you can support the podcast and get great benefits by becoming a Member at a special rate of 30-40% off. You'll not only help me work, but also get paid subscriber access to Substack, an exclusive monthly solo podcast, Member-only Zooms, and access to a private Slack community discussion group.

You can become a Member annually for $360/year - 40% off the regular monthly price: https://www.aaronrenn.com/subscribe?selectedPlanId=founding36000usd

You can also become a Member monthly for $35/month - 30% off the regular price: https://www.patreon.com/aaron_renn/membership

Thank you so much for your support. Send me your podcast feedback and suggestions.