How to get that effortless JFK Jr. Style
It’s no surprise that the fashion kids in TikTok are going wild over 90’s nostalgia - and it’s easy to see why. Arguably, the clean, sun-drenched and aspirational 90s vibe was the last time the culture seemed to have it’s own aesthetic - one unaffected by social media and the boom in connectivity and technology - being the last great era where humans interacted with each other more in person, and were not glued behind a screen.
Effortless, but never accidental—that’s the quiet magic of ‘90s style at its absolute peak. Long before “quiet luxury” became a tired hashtag, JFK Jr., a staple in tabloids and on 90s magazine covers, mastered a kind of undone polish that felt equal parts Ivy League heir and downtown heartthrob. Think crisp oxford shirts worn like an afterthought, perfectly broken-in blue denim, fashion that whispered money rather than shouted.
And now, with the glossy arrival of Love Story, the aspirational and chic world of 90s fashion —along with the minimalist cool of Carolyn Bessette—is back in heavy rotation, reminding us all that true style isn’t about trying harder, it’s about the accents and details. So if you’ve ever wanted to look like you oozed enough prestige and wealth to just throw something on and somehow became the best-dressed man in the room, consider this your starting point.
Double-breasted captain's blazer in English wool - J. Crew
This is the foundation piece for any 90s inspired JFK Jr outfit - and the piece from American preppy brand J. Crew is perfect. Nothing defines the 90s more than this double breasted design, and the tailoring and English wool scream wealth and prestige. Opt for navy, and couple with jeans or chinos, and people will be stopping you on the street for outfit advice in no time.
Relaxed, wide fit cotton chinos - COS
These are a great, sandstone neutral colour, baggy enough to fit in with the 2026 vibe, while also creating a relaxed enough silhouette to nod to the 90s. This is an essential to add to your wardrobe.
Mens 90’s Inspired Striped Tie - H&M
Part-preppy, part posh - this classic menswear striped tie in college colours will add a 90’s JFK splash to any outfit. Pair with an oxford shirt, chinos and boots for that polished but effortless President’s Son look.
Classic White Oxford Shirt - Polo Ralph Lauren
Irrespective of whether you want to emulate JFK Jr. or not - every man needs a crisp, classic White Cotton Oxford Shirt in his wardrobe - and you can’t go wrong with this iconic slim fit blue label offering, from the house of Ralph Lauren.
90’s Inspired, Slim Rectangular Sunglasses - ASOS
For that 90s look, you want a pair of slim, rectangular sunglasses in a tortoise-shell or equivalent colour. These from ASOS so the trick - they are smart, stylist, and cheap - and will finish off that effortless JFK Jr. style look.
Vintage New York Yankees Baseball Cap - New Era
No JFK Jr. 90’s outfit would be complete without some appropriate headwear. This vintage NY Yankees piece from official outlet New Era would do the trick nicely. Go with this camel colour if you are wearing denim or olive coloured chinos, otherwise opt for a green or navy colour if you are pairing with brown or sandstone for that 90s contrast. Don’t forget - you don’t want to be too matchy or to clash with yourself.
Vintage Levis Denim - North Workshop
Another staple for any man’s wardrobe. There’s a specific type of blue that defines the 90s and this is as near to it as you can get. Deep blue, slightly stonewashed, completely vintage. You can’t go wrong with the original Levis, and the 505s have that distinctive relaxed 90s look. This pair from UK Vintage Outlet - North Workshop would look beautiful as part of any 90s JFK Jr inspired outfit.
90’s Inspired Desert Boots - Calvin Klein
These brown suede desert boots scream 90s style, and how much more 90s can you get than this offering from the era-defining 90s fashion label - Calvin Klein. Ideally paired with some vintage blue denim, these are the finishing touches that will lift your outfit from inspired to stunning.
90s Inspired Vintage Black Leather Belt - Zara
Any 90’s inspired outfit wouldn’t be complete without a metal buckle black leather belt - remember, this era was all about the accents and little details - and this offering from Zara works perfectly. Paired with either chinos or jeans, it would work perfectly and look the real deal when going for a JFK Jr inspired fit.
https://www.zara.com/uk/en/vintage-effect-leather-belt-p05919405.html?v1=496266177
Checked Burberry Men’s Scarf - Burberry
Nailing the 90s JFK Jr vibe is all about the accents and details, and nothing speaks quiet luxury and effortless presidential wealth more than iconic British label Burberry. This scarf would be the perfect accent to a JFK Jr outfit, effortlessly tossed around an oxford shirt and coat, and don’t forget the tousled hair.
