The images are iconic now—a rolled-up sleeve, an untucked shirt, a shaggy head of hair—like something out of a J.Crew catalog or a Ralph Lauren advertisement. But in 1961, Kennedy's confident, carefree style was a radical departure from the copycat boxy gray suits and felt hats that had defined men's fashion for previous generations.

The images are iconic now—a rolled-up sleeve, an untucked shirt, a shaggy head of hair—like something out of a J.Crew catalog or a Ralph Lauren advertisement. But in 1961, Kennedy's confident, carefree style was a radical departure from the copycat boxy gray suits and felt hats that had defined men's fashion for previous generations.

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