Why Men Don’t Dress Up Anymore

The Timeless Gentleman
Oct 20, 2026

There was a time when dressing well wasn’t considered dressing up. It was simply how men were expected to present themselves. So what changed?

In this video, we look at how rebellion, changing workplaces, the rise of comfort, fast fashion, Silicon Valley, remote work, and a more casual culture gradually changed the way men dress, and whether we lost something along the way. Enjoy!