If you have spent any time online over the past few weeks, you will already be aware of Love Story, the new FX and Hulu series about the relationship between John F. Kennedy Jr. and Carolyn Bessette, created by Ryan Murphy. Since its premiere on February 12, the show has not left the cultural conversation. In its first five episodes, Love Story accumulated more than 25 million viewing hours, making it the most-watched limited series in FX history. Searches for JFK Jr. reportedly increased by more than 9,100% in the month following its debut.
Most of that conversation has centred on Carolyn Bessette Kennedy: her minimalist wardrobe, her Calvin Klein sensibility, her studied nonchalance. But the men’s style story has been building quietly in the background. Because if Carolyn was the definitive embodiment of 1990s understatement, John Jr. was something else entirely: a man who took the preppy playbook as his starting point and then broke every rule in it with a grin. Right now, that is exactly the energy men’s fashion is reaching for.
Who John Jr. Was, Stylistically
JFK Jr. had an advantage that most men could only dream of: he came from the most scrutinised wardrobe in American political history and used it as raw material rather than a restraint. The Kennedy family represented a very specific kind of elegance: Ivy League tailoring, naval heritage, New England restraint. John Jr. absorbed all of it before systematically dismantling it.
As the show’s costume designer Rudy Mance has put it in interviews, JFK Jr. comes across as one of the original New York male hipsters. He wore sportswear with the ease of someone who had grown up in suits, and suits with the recklessness of someone who genuinely did not care what you thought. An Armani jacket over hiking boots. A backward baseball cap on a bike. A navy blazer over a white T-shirt, worn as though it were the most obvious thing in the world.
When he launched George magazine and suits became a professional necessity, he still subverted them. The collar stayed open. The tie was loosened. The shoes were never quite right. That slight wrongness, deliberate or not, was the whole point.
The Wardrobe Breakdown
Understanding JFK Jr.’s style means understanding what shaped it. This was not an overly complicated wardrobe. It was a wardrobe of high-quality basics, worn with the confidence of someone who never once questioned whether something would work.
Start with the blazer. A well-cut navy or camel blazer was the cornerstone of JFK Jr.’s look, and it remains one of the most versatile pieces a man can own. The key is fit: slightly relaxed in the shoulder, clean through the chest, hitting just above the hip. Drake’s, Oliver Spencer and Sandro are currently producing exactly this shape across a range of price points.
Beneath it, a plain white or off-white T-shirt or crew-neck knit. JFK Jr.’s greatest contribution to men’s fashion may well be his use of contrast as a signature move: the formality of the blazer makes the T-shirt feel considered, and the casualness of the T-shirt keeps the blazer from feeling stiff. A heavyweight cotton T-shirt from Sunspel or James Perse, or a fine merino crew-neck from Inis Meain or Begg & Co, does this effortlessly.
The trousers were always clean: straight cut or slightly tapered, in khaki, navy or grey flannel. No break over the shoe. Nothing that invited a second thought. Corridor and Incotex both produce excellent versions, while Orlebar Brown offers similar options that sit comfortably within the same clean register.
Footwear is where it gets interesting. JFK Jr. mixed and matched without apology. Loafers, specifically penny or tassel styles from Alden or G.H. Bass, were a constant. But so were clean white sneakers, boat shoes, and the occasional hiking boot worn somewhere it had no business being. The lesson is not which shoe to wear. It is the confidence with which you wear it.
Finally, the outerwear. The show has already reignited interest in the classic trench coat, but JFK Jr.’s more practical default was the Harrington jacket or a simple waxed cotton field jacket: workwear heritage worn as an everyday mode. Baracuta and Barbour remain the definitive references for both.
How to Wear It Now
The good news is that this approach maps almost perfectly onto where menswear is heading in 2026. The industry is moving toward quality, restraint and longevity, and what JFK Jr. wore was essentially a masterclass in that way of thinking, executed without any self-consciousness.
The entry point is simple: a navy blazer, a clean knit, straight trousers and a good loafer covers most occasions and creates the foundation of the look. From there, introduce the mix-and-match irreverence that made it his. Wear the blazer with chinos and white trainers. Wear the loafers with denim. Let the collar of your shirt sit open when the jacket would suggest otherwise.
The Key Pieces
Navy blazer: Drake’s, Oliver Spencer or Sandro. Budget option: Charles Tyrwhitt or Reiss.
Heavyweight cotton T‑shirt: Sunspel Classic Tee (around $100) or James Perse (from around $90).
Merino crew‑neck knit: Inis Meain or Begg & Co at the top end; Uniqlo’s knitwear for value.
Straight chinos or trousers: Corridor NYC, Incotex or NN07.
Penny loafer: Alden or G.H. Bass for the purist; Mango or ASOS for the price‑conscious.
Harrington jacket: Baracuta G9 — the original and still the best (around $380).
