What Replaced It: Unstructured Sportcoats

The "Italian sprezzatura" thing never quite caught on, and Ralph Lauren Rugby went out of business. As much as you convinced yourself you could wear this thing—brass buttons and all—with jeans and chinos, you couldn't help but feel slightly dickish when you walked into class or the office. Perhaps, you've got for soft-shouldered, patch-pocketed single-breasted blazer already. You wear it with casual button downs and solid tees, and it does its job. You feel more comfortable, and less like a fashion victim.