Believe it or not, at one time the two were not mutually independent. Fashion and youth have ever been kissing cousins, especially since the period between the wars. But for a glimpse of some great costuming, drop “JFK – Reckless Youth
Sure, he wore tennis shoes with his khakis and sweatshirts, but that’s forgivable in my book. Patrick Dempsey also gets to cavort in evening clothes, double-breasted suits (like the one above that he wears in London), tweeds, Tattersall shirts and all the other kit of a preppy kid before WWII. It’s worth a bit of your time, if just for inspiration about being comfortable in your clothes.