The internet's fascination with American Love Story – the latest instalment in Ryan Murphy’s anthology universe – has put John F. Kennedy Jr. and Carolyn Bessette-Kennedy back into pop culture's orbit. And as we revisit their relationship, we're also rediscovering the particular magnetism Kennedy Jr. in particular brought to public life. He dressed with the ease of someone who understood both tailoring and optics.
Like anyone from a political dynasty, we need to start with his suits. He favoured traditional American tailoring – structured shoulders, a clean chest – often pared-back with a reversed baseball cap or a slouchy leather overnighter. Think navy or charcoal two-button suits, often single-breasted, cut close but not fashion-forward slim. Brands like Ralph Lauren Purple Label, Armani and Brooks Brothers align with what he wore: conservative lines, natural fibres, and an all-American label. Of course, he also donned plenty of Calvin Klein (where he met his wife, Carolyn). He usually paired his tailored pieces with repp ties or simple silk solids, crisp white or pale blue shirts, and black or dark brown cap-toe Oxfords. The silhouette was tidy and vertical, nothing exaggerated. And of course – almost always topped off with his signature backwards flat cap.
Off duty, the formula was much more playful, stayed disciplined to his personal aesthetics. He relied on straight-leg jeans –mid-rise, not skinny – worn with a brown leather belt and loafers or desert boots. The jeans were often classic Levi Strauss & Co. 501s: rigid denim, but strictly no distressing (it's important to discern 'worn' from 'distressed' here as they were certainly lived-in). On top, he rotated between oxford cloth button-downs, fine-gauge crewneck sweaters, half-zip fleeces and blazers.
Being an NYC resident – outerwear mattered. Kennedy wore double-breasted navy topcoats with peak lapels in winter, and simple Harrington or bomber jackets in transitional weather. The lines were clean, the colours restrained – navy, camel, olive. Nothing oversized, nor aggressively trendy.
But don't get it wrong – JFK Jr. also understood how to summer. For Hamptons holidays and aboard private yachts, he favoured tailored shorts with a trim polo or a linen shirt, boat shoes without socks, tortoiseshell sunglasses – often Ray-Bans. For him, it was about knowing which American staples – navy suits, OCBDs, 501s, loafers – still worked, and wearing them with precision.
Below, we round up some of our favourite JFK Jr. style moments from over the years.
