Uploaded January 2026 | Updated September 2026, 1 week ago
* The best leather bags and backpacks for grown up men: badleathergoods.com/collections/leather-bags
* Subscribe to @PetersPrism and @thesecondbutton !
* The Satchel & Page backpack I love: stridewise.com/satchel-page-backpack
* My favorite leather messenger bags stridewise.com/best-leather-messenger-bags
* Stretch vs non stretch denim explored at a jeans factory: youtube.com/watch?v=XXjxsdVfyQ8
As Millennials enter their forties, youth culture shifts, and brands grapple with the surprisingly distinct differences between that generation and the hipper Gen Z, it’s time to ask the question: is anything about the way Millennials dress actually timeless and fashionproof, or do we all need to update our wardrobes? I’m as clueless as anyone, so to help me answer this question I invited two menswear gurus to discuss the trends and styles they think Millennials need to retire.
00:00 Millennials are turning 40!
00:42 Dress sneakers
02:01 Wacky socks
02:43 Skinny jeans
05:31 Stretchy synthetics
09:00 Ugly backpacks
11:36 Why care what menswear guys think?
* The best leather bags and backpacks for grown up men: badleathergoods.com/collections/leather-bags
* Subscribe to @PetersPrism and @thesecondbutton !
* The Satchel & Page backpack I love: stridewise.com/satchel-page-backpack
* My favorite leather messenger bags stridewise.com/best-leather-messenger-bags
* Stretch vs non stretch denim explored at a jeans factory: youtube.com/watch?v=XXjxsdVfyQ8
As Millennials enter their forties, youth culture shifts, and brands grapple with the surprisingly distinct differences between that generation and the hipper Gen Z, it’s time to ask the question: is anything about the way Millennials dress actually timeless and fashionproof, or do we all need to update our wardrobes? I’m as clueless as anyone, so to help me answer this question I invited two menswear gurus to discuss the trends and styles they think Millennials need to retire.
00:00 Millennials are turning 40!
00:42 Dress sneakers
02:01 Wacky socks
02:43 Skinny jeans
05:31 Stretchy synthetics
09:00 Ugly backpacks
11:36 Why care what menswear guys think?
