The Biggest Classic Style Wins and Fails of Every Generation

About this video

The Gazette team presents a comprehensive review of men’s fashion wins and fails across seven generational eras from 1901 to 2024. They examine iconic achievements like the invention of the lounge suit, the standardization of black tie formal wear, and the mainstreaming of denim, while also critiquing major fashion missteps such as Oxford bags, extreme maximalism in polyester, and overly skinny formal fits. The analysis demonstrates how each generation’s clothing choices reflected broader cultural shifts toward casualization and self-expression in men’s style.

Key takeaways

• The Gazette team argues that the lounge suit revolutionized men’s wear by replacing impractical frock coats and establishing the three-piece suit as the standard for polite society
• The Gazette team contends that the baby boomer era’s oversimplification of men’s wear—reducing color, pattern, and accessories—contributed to suits gaining a negative ‘stuffy’ reputation that persists today
• The Gazette team credits Generation X and millennials with mainstreaming casual shirt styles like polos and denim, which transitioned from leisure wear into everyday business casual staples
• The Gazette team identifies Gen Z’s destigmatization of male grooming and fashion interest as a positive cultural shift that combated harmful stereotypes about masculinity

Episode details: published April 25, 2025 · 22K views · 12:13 long. Summary written by Self Growth Videos from the episode itself. The style guidance summarized here is the Gentleman’s Gazette team’s own teaching and opinion, presented for education; product recommendations are theirs, not ours. Summaries are written by Self Growth Videos from each video itself.

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