Recreating Looks from My Unexpected Style Icons, Part 2
Casual summer looks from JFK Jr., Robert Redford, Richard Gere, and more.
It can take me a minute to warm up to a new season. Getting used to different temperatures, humidity levels, and ways of dressing can feel like a quick gear change and often, not one I’m quite ready for. So, like the start of every new season, I recently spent a bit of time looking back on what I was wearing this time last year (I know we like to moan about Instagram, but documenting one’s outfits can be helpful). I scrolled through the images I’ve saved on my seasonal Pinterest boards. And I looked back at what I was writing about on Substack.
This time last year? It was my unexpected summer style icons: the ease of the outfits Ralph Fiennes wore in The English Patient, Harrison Ford’s iconic Cannes outfit of a navy jumper and shorts, and old J. Crew summer catalogues from the 1980s and ‘90s.
It inspired me to look through all of my other saved images. What am I saving, and why? And yes, I unearthed some more unexpected style icons. Like Bill Cunningham and his iconic blue chore jacket. Richard Gere and the shirt and jeans outfits he often sported in the ‘80s. And JFK Jr. with his slouchy ‘90s tailoring.
I’m a fan of menswear and, like last summer, I’m leaning towards the easy, everyday looks worn by men in years gone by. No over-styling, no overthinking, just practical pieces and combinations. Here’s how I’m recreating them.
JFK Jr.’s casual tailoring
Much is said about the style of Carolyn Bessette Kennedy. And rightly so, she was the queen of ‘90s minimalism, and her simple-yet-chic way of dressing has made it onto many a mood board since. But honestly, out of her outfits and JFK Jr.’s? It’s often his looks I’m drawn to most. And for summer, I’m drawing inspiration from this: an unbuttoned blue shirt roughly tucked in and rolled at the cuffs, light slouchy linen trousers with a touch of tailoring, and easy sandals.
I bought this Armor-Lux shirt during a trip to Brittany last summer — the French brand’s home region. It’s 100% linen and has that lovely slubby feel to it, and it’s as easy to throw on over swimwear at the beach as it is to wear day-to-day, like with this look. Taking a leaf out of JFK Jr.’s book, I’ve paired it with off-white trousers that are loose, yet have a touch of tailoring — but I’m leaving the shirt untucked so it doesn’t look too polished. Finished, of course, with trusty Birkenstock Arizonas.
Bill Cunningham’s French workman’s jacket
Bill Cunningham: a true icon in the fashion world. Not only was he one of the original photographers of street style, reporting for The New York Times until his death in 2016, aged 87, but his signature style became the stuff of legend — completely unintentionally. Bill’s classic French workman’s jacket was always on his back, just going to show that sometimes, it’s the pieces that are so worn-in that they feel like a second skin that work best.
Unlike Bill, I didn’t pick my jacket up from a French hardware store (or so the story goes), but from British brand Gloverall. It has the same features though: the chunky buttons down the front, the lightweight yet hardy cotton, the deep pockets and the royal blue shade. It’s the perfect light layer for spring and summer. Inspired by Bill, I’ve kept the rest of the outfit simple — black linen trousers, a black T-shirt and classic canvas trainers. Because there’s no need to overthink it.
Richard Gere’s black jeans and unbuttoned shirt
This isn’t the first time Richard Gere has been my source of inspiration. Last autumn, I wrote about how he had me reaching for oversized blazers. But as we creep ever closer to summer, I want less structure, fewer layers, and looser fits — like this look (I live in the UK, so I won’t be packing my long sleeves and denim away anytime soon). According to my research, this picture was taken in 1987, but it can very much work for 2025 too.
I featured this outfit in a post a couple of weeks ago, when I rounded up my favourite comfy outfits for spring. It was only when I was scrolling through Pinterest a few days ago that I realised just how similar it was to Richard’s look above. Maybe it’s a coincidence. Or maybe I’ve absorbed this image into my subconscious without realising it. Whatever it is, this is a version of that look from the 1980s with a couple of tweaks to make it feel more like “me”: a slightly slouchier shirt, jeans that are more of a loose fit, and silver rings instead of a shiny gold watch.
Robert Redford wearing knitwear at the beach
This isn’t the best image, and I can’t find the exact year, but the vibe of this outfit is what I love about summer — especially a British summer, where a light jumper is often a necessity. In reality, there’s not much to it: a navy jumper, khaki trousers and sun-kissed skin. But simplicity and not overthinking things is the kind of summer dressing I can get on board with (I recently wrote about embracing an effortless summer, after all).
Here’s my version. The navy cashmere jumper is lightweight, super soft and comfortable to wear — an excellent layer all year-round. I’ve popped a T-shirt underneath because it’s always handy to have something there if it does get hot and you want to shed the knitwear (plus, having that little pop of contrasting fabric can make a big difference to an outfit). Next up, I’ve gone for my (very well-worn) linen khaki barrel-leg trousers from Beyond Nine, and because I’m just not a loafer person (sorry, Robert), my go-to fisherman sandals are my footwear of choice.
Jude Law in a suit and flip-flops
A suit and flip-flops? Shouldn’t work. Not really. One element is very structured, smart and formal, and the other is… decidedly not. But sometimes it’s these contradictions that work best, as this Jude Law look from 2010 (according to my research on the internet anyway, which I fully believe — those sunglasses are very of their time) shows. It works because the suit isn’t overly formal. The trousers are rolled up at the hem, and the T-shirt makes it feel a lot more casual than a shirt would, so the flip-flops feel like a natural choice rather than a jarring one.
I got this Toast suit recently, and I’ve been wondering about the different ways I can wear it over summer, so that image of Jude’s styling came at an opportune moment. The jacket and trousers are both made from a cotton-linen blend. They’re already pretty casual, so they work well for this kind of look, but pairing them with a classic white T-shirt (this is the Soho from WNU, quite possibly a new contender for my favourite white tee) and flip-flops makes it feel very wearable day-to-day. Thank you, Jude circa 2010.
Any items marked with * have been gifted by brands. All thoughts, picks and reviews are my own.
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Great examples! And I would and could wear all of them. I even have a royal blue work jacket type thing. The only difference is that I’m more inclined to incorporate more vivid color especially in the summer. Yesterday I wore an oversized blue striped shirt with raspberry linen pants. But the shapes were similar.
These are amazing inspirations!! (Also all of them such handsome men with incredible style! 🤩). Quick question: the Salt Water Franciscan sandals are sold out in my size, any other brands you can recommend for this specific style? Thanks!