The first time John F. Kennedy Jr. really caught my attention was during my senior year of high school, amidst a business competition. I had the brilliant idea of creating a magazine, and my teacher suggested I look up George to help me figure out how to structure it. Upon his suggestion, I looked up the inaugural issue of George, gawked at the Cindy Crawford cover, and promptly went back to my initial idea. (As fate would have it, I ended up clinching third place with my magazine pitch—not too shabby. Although, it's worth mentioning that only three contestants participated, so in a sense my idea was a losing one, haha!) Last year, I found a copy of the inaugural issue for $5, and when I started flipping through it, I realized my teacher was right— I should have looked into George.
Fast forwarding to today, it seems like JFK Jr. and his wife, Carolyn, are once again the talk of the town. That’s not to say they haven't been a fixture on mood boards or in people's thoughts before, but with the release of Sunita Kumar Nair’s book CBK: Carolyn Bessette Kennedy: A Life in Fashion (Ryan Murphy is also working on a show about them as well), the discussion around the couple and their style feels heighten.
The inspiration for this letter struck me on Tuesday after reading a piece by Sam Hine for GQ. It featured a conversation with Challenger’s costume designer, Jonathan Anderson, discussing Josh O’Connor’s JFK Jr. coded wardrobe (you've probably seen the “I Told Ya” t-shirt, which is a remake of the one that JFK Jr. wore). This interview also brought to mind a WSJ fashion spread from earlier this year that I went completely gaga for ( you can find a few images from the spread in my mood board letter), even driving me to consider purchasing a pair of Nike shorts.
All of this together made me think to myself, "By George, I think it’s going to be a JFK JR. summer—style-wise, of course!"
When I started shuffling through the photos of John Jr.—shirtless, on a bike, in suits, or hobbling on crutches—I began to really question what it is that makes them so stylish. In fact, in some of these photos, you could describe him as a devilishly handsome slob! Yet, beyond his last name, there's a relatable humanity to John and Carolyn captured in these images. They were, in a way, "working royals"—Carolyn working in public relations for Calvin Klein, and John with his magazine. (And let's not forget the humbling experience of the public witnessing his bar exam struggles.) Or perhaps it is just the timeless enchantment of Camelot.
So when it came time for me to put together these JFK Jr. coded looks, I thought less about trying to recreate looks to a tee. My focus was on capturing the essence of his style, which epitomizes nonchalance—which is the ideal approach for dressing for the warmer weather. You don't necessarily want an outfit that's too overworked; you want layers that are breathable and, more importantly, that make you feel like yourself! To distance myself from his specific wardrobe choices, I deliberately avoided browsing images of him the day before putting together these looks. This allowed me to trust my instincts and let creativity take the lead, rather than being bound by what he actually wore. So dear reader I hope you enjoy my take on JFK Jr.!
LOOK 1: THE SUIT
PIECES FEATURED:
Stoffa linen suit and suede trainers
L.L. Bean monogrammed wrinkle free classic oxford
Sky High Farm bandana
Puck baseball cap
VTG Chanel tie (look at these other great options from Etsy: here, here, and here)
This look is undoubtedly inspired by one of the many photos of him in a suit. When you examine those images, you notice the classic 90s proportions—broad shoulders and slightly oversized, but not to the extent that he appears engulfed by the suit. This particular suit is from Stoffa. I first heard about the brand toward the tail end of the pandemic, and in 2021, they invited me to model for them. This coincided with my inaugural viewing of American Gigolo (1980), and upon meeting Agyesh Madan, I couldn't help but comment on how his clothes looked like they came straight out of the Richard Gere film.
When it comes to similar suiting, you can't go wrong with Armani, often available at great prices secondhand, and even Banana Republic has been making some convincing styles. Also, when was the last time you thought about Donna Karan’s menswear line? For the Stoffa store opening, I opted for a red bandana to complement my red tie (mine is from Sky High Fram). Alternatively, I think a nice Charvet scarf would also pair well with this look. However, I found the Puck baseball cap to be quite an interesting option. Would JFK Jr. be a Puck reader? I think so!
LOOK 2: THE JOCK
PIECES FEATURED:
VTG Armani trench coat (here’s one on Etsy)
Stoffa practicewear (I also love VTG Russel)
Charvet shirt
New Balance 990v4
Yali Milano hat
Elisa Johnson sunglasses
Hermes canvas knapsack
Dorsey tennis bracelet
When I've come across images of JFK Jr., it's usually him in a sharp suit or sporting more casual attire. These sweats I'm wearing are all from Stoffa, and unlike some in the fashion world, I don't turn up my nose at sweatsuits. In fact, I find them quite exceptional. I particularly love vintage Russell sweats, especially if they have some random school paraphernalia plastered over them. I also have a soft spot for certain styles from Champion or Kule, and last summer, I became oddly obsessed with a pair of sweat shorts I snagged from Cuffy’s. To elevate the sweatsuit's look, I paired it with a button-down shirt, inspired by Carolyn Bessette, a tidbit I gleaned from a conversation Rachel Tashjian Wise had with Nair about her book.
LOOK 3: THE MARTHA’S VINEYARD BEACH RAT
PIECES IN THIS LOOK:
Dries Van Noten mesh polo (here it is in black)
Polo Ralph Lauren linen shirt
VTG cut-off denim shorts ( I quite like these from Agolde)
Tomas Maier hush puppies (try these from The Row)
Straw hat (here is an option here, here, and ooo what about this one!??!)
Isabela Capeto drawstring bag
This ensemble is taking more cues from late 70s/early 80s JFK Jr. when he was bopping around with a mop full of curly locks and shorts that were quite short. This is also a variation of this layering look from a previous letter (see
it’s a good thing I kept this Dries polo!!!). I prefer to make my own denim cutoff shorts rather than buy them. This way, I have more control over the length and can experiment with fraying. These particular shorts are fashioned from vintage 501s, and I trim them a bit shorter each year. While I adore this outfit, if there's one change I'd make, it would be the belt. A braided belt from Charvet would be perfect—polished yet quirky, and available in a variety of colors!Pieces Featured:
Floral beaded necklace from Etsy
Rene Barnes gold nugget necklace
Renato Cipullo chain, letter pendant, and zodaic pendant
Lemaire castanet (you could either buy a real castanet and put it on a leather string, or what about the completely bonkers Lemaire bird whistle necklace?)
Dorsey tennis bracelet
I went all out with the jewelry for this look., which is of course more of a JJ characterization versus a JFK Jr. one. I believe the key to layering jewelry lies in mixing pieces with different textures, colors, and silhouettes. Typically, I'd include my diamond tennis necklace; there's something about the sparkle of diamonds combined with a quirky charm necklace that's just captivating. However, this time, I went for a beaded necklace adorned with baroque pearls and floral beads. Unfortunately, the Etsy shop where I found it is no longer available (this one from Etsy is similar), but I'd suggest checking out brands like Lizzie Fortunato (who made my fish ring), Don’t Let Disco, and Bleecker & Prince. The latter offers delightful pendants with scattered diamonds!
Pieces Featured:
Anklets (top) Miansai necklace used as an anklet, and (bottom) Santangelo
I felt like anklets complemented this look perfectly, and I've been experimenting with new ways to wear necklaces that I don't often reach for or feel a bit snug around my neck. That's exactly what I did with the Miansai necklace, which I truly adore but rarely seem to wear. Santangelo offers fantastic jewelry, and designer Anna Santangelo collaborated with Proenza Schouler a few years ago, creating a fabulous collection that I still think about to this day!
LOOK 4: THE “OFF-DUTY”
PIECES FEATURED:
Alex Mill storm trench (I’m wearing a large)
The top and shorts are also Alex Mill, and they will be released soon:) they are absolutely divine. In the meantime check out this top and pants that are similar!
Larroude Yves wedges
Gigi Burris sailor hat
VTG corsage from Etsy
I know what you're thinking—JFK Jr. and wedges don't quite align. I share that sentiment; I think he is more of a Cuban heel guy. But I digress. When it comes to 'off-duty' wear, my mind leans toward workwear or military-inspired pieces because of the functionality of the pieces. I've been longing for a double-pocket linen Safari shirt, and this one from Alex Mill fits the bill perfectly (it's coming out soon, along with the shorts!). I’m wearing a medium, it's slightly oversized, striking the right balance without drowning me in fabric. For some, heels or wedges aren't the epitome of 'off-duty' attire. Yet, in my world, norms flip—heels for day, flats for night! This outfit speaks more to my approach to dressing, but it echoes JFK's pragmatic approach.
LOOK 5: THE HYANNIS PORT COMPOUND
Pieces Featured:
Alex Mill linen work jacket (medium)
Bode x Nike “Cape Cod” jersey
AYR The Pal in Corduroy
Madewell denim shirt (tied around waist)
Ray-Ban sunglasses
I mean, could I do a JFK Jr. inspired post without wearing my Cape Cod jersey? I don’t think so, that would be pure blasphemy, no? Hahaha! Mitchell Nugent from Interview Magazine wrote this ode to the boy wonder and the Loewe remake of his shirt, and I loved his retelling of his mother’s memories of seeing Jackie throw a football to John Jr. and his friends at the Boston Common. It was such a romantic retelling that the idea for this outfit somewhat popped into my head as I was reading through his piece. (Longtime readers may also remember Nugent from my piece dedicated to the popularity of books!)
This look epitomizes nonchalance, with the relaxed proportions of each piece effortlessly draping over the body. The interplay of textures, from the jersey to the linen of the Alex Mill jacket and the oh-so-comfortable AYR corduroy pants, adds depth and interest to the ensemble.
See you all mid-week, and be sure to tune in next Sunday for another edition of “Wear Test,” where I'll be putting this Tory Burch dress and cape to the test! It's going to be fun!
xx
JJ
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I love this not only for its outfit ideas but also as a guide for interpreting the gestalt of a look/persona through versus needing to crib the pieces. So inspired.
You in that suit look is 10/10...chef's kiss!!!
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