The old saying “what goes around comes around” has never felt more relevant in fashion. Many of the new spring season’s biggest trends are, in fact, not very new at all.
From specific items such as ballet shoes and pilot sunglasses, to perennials like white shirts and easy denim, the pieces that many of history’s greatest style icons championed in their heyday are in vogue once again.
So pick yourself a pin-up – be it Jane Birkin or Grace Kelly, Jackie Kennedy or Princess Diana. Here’s how to copy their timeless outfits, with just a little modern twist.
Princess Diana
Pilot sunglasses, £139, Ray-Ban; Ecru belt, £65, Boden; Gathered blouse, £87, & Other Stories; Linen blend trousers, £150, Reiss
The pilot-style sunglasses that Princess Diana wore in 1983 are set to be the shape to wear once again this summer. The ingredients of the rest of her outfit (pale wide-leg trousers, a cream blouse and pumps) are each also great spring wardrobe updaters. The belt is a crucial finishing touch – swap your staple black style for a lighter colour as soon as the sun shines and it will lift your whole look.
Grace Kelly
Hera earrings, £175, Missoma; Relaxed shirt, £75, Cos; Wide belt, £475, Loewe; Bangle set, £135, Shashi at Liberty
The oversized white shirt has endless appeal – but note how the ladylike styling tricks employed by Kelly in 1955 look as effortlessly elegant today. The turned-up sleeves and the use of a wide brown belt serve to show dainty wrists and jewellery, and cinch the waist respectively. Just add some bold gold earrings, which are also trending again, and a more sculptural contemporary bangle.
Audrey Hepburn
Capri pants, £240, Faithfull at Net-a-Porter; Azalea cardigan, £125, Aligne; Leather pumps, £56, Marks & Spencer
Gingham is always a spring outfit sweetener – and on Hepburn in 1955 it looked especially girly. Capri trousers are once again on trend, but to make the look more grown up, try a peplum knitted cardigan and block-heel pumps, rather than ballet flats.
The Duchess of Windsor
Flower brooch, £95, Essentiel Antwerp; Spot print dress, £149, Whistles; Patent heels, £335, The Fold
Wallis Simpson’s navy polka-dot dress looks like something from the latest Alessandra Rich collection. Her penchant for jewellery in sweet-wrapper colours is also noteworthy in 2026. “Floral brooches are the perfect spring wardrobe update,” notes Inge Onsea, co-founder and creative director of Essentiel Antwerp. “They give such a playful yet polished flourish to everything from blazers to soft knits.” This entire look, with wine-colour leather heels, would be particularly appropriate for an early spring wedding guest.
Diana Ross
Jersey top, £110, Jigsaw; Ring, £450, Dior; Belt, £395, Sonia Petroff; Embroidered skirt, £186, Rodebjer at Farfetch
If you’re off to any sort of party or occasion this spring, then you’d struggle to select a more fun fashion pin up than Ross. This 1966 photograph of The Supremes offers up three great outfits to take inspiration from. But Ross’s mixing of blue and metallics hues, particularly, feels fresh again for now.
Princess Margaret
Bronagh waterproof jacket, £299, Barbour; Gingham rain hood, £43, Capuches A Mémé at Semaine; Bouquet silk scarf, £185, Liberty
It may be spring, but it will inevitably rain at some point. This photograph of Princess Margaret was taken at the Badminton Horse Trials in Gloucestershire in April 1961 – Margaret styled a taupe-colour anorak with a knotted silk scarf beneath. To nod to the ladylike, layered-up look today, invest in a rain hood from the Parisian brand Capuches A Mémé, and use a scarf to inject some much-needed colour and pattern too.
Jane Birkin
The Classic shirt, £95, With Nothing Underneath; Nantucket bag, £405, Dragon Diffusion at Harvey Nichols; Cuff jeans, £360, Frame; Jonna sandals, £100, Vagabond
Birkin loved a crisp white shirt (and yes, pale blue is just as timeless). The pieces in this outfit are ones that every woman owns – but it’s about what you do with them. “It’s all in the accessories,” says Pip Durell, the founder of British shirting specialist With Nothing Underneath. “A strapped sandal and rolled sleeves shows a bit of skin, while the navy jumper thrown around the shoulders adds both polish and practicality to the look. Her style is a great balance of chic without foregoing function, which is why we all return to her inspiration.”
Jackie Kennedy
Single pleat linen trousers, £46, Marks & Spencer; Classic shirt, £120, With Nothing Underneath; Ruby bag, £99, JW Pei; Double necklace, £15.99, Mango; Jeanne sunglasses, £150, Jimmy Fairly
A linen shirt and trousers co-ord is a pairing you will use throughout spring and summer – worn together or separately. As this picture of Kennedy in New York in 1970 illustrates, navy looks particularly chic. Especially when you accessorise with gold jewellery and signature oversized sunglasses.