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How to wear Nineties trends in 2026

Carolyn Bessette on Madison Avenue.
Carolyn Bessette on Madison Avenue. New York, US.

If your feeds have felt like a time capsule recently, you’re not imagining it.

From the renewed fascination with Carolyn Bessette-Kennedy’s wardrobe to queues forming outside New York’s C.O. Bigelow to buy her signature tortoiseshell headband, Nineties minimalism is firmly back in fashion.

"After a long stretch of trend-heavy dressing, people are craving something more refined," says luxury stylist Oriona Robb. "They want pieces that feel expensive rather than attention-seeking."

Carolyn Bessette-Kennedy
Carolyn Bessette-Kennedy has been the poster girl for a renewed interest in minimalist Nineties fashion (Alamy/PA)

So why is Carolyn Bessette-Kennedy at the centre of this shift? Well, her pared-back wardrobe has once again become a reference point thanks to FX’s Love Story: John F. Kennedy Jr. & Carolyn Bessette.

"She had a very clear point of view," Robb explains. "There was never too much going on, no over-styling, no unnecessary extras, just really well-chosen pieces worn with confidence."

So which Nineties staples are worth revisiting now? Stylists give their five top picks.

1. The slip dress

Few pieces capture Nineties minimalism quite like the slip dress. Long associated with Bessette-Kennedy – most famously on her wedding day – it has re-emerged as a key silhouette this season.

Today's version is more about how it’s styled in order to bring it into 2026.

"Slip dresses work best when they’re layered," says stylist Elsa Boutaric, "a blazer or a soft knit instantly makes them feel more wearable."

Joey Lauren Adams attends the premiere of 'Big Daddy' in 1999
Joey Lauren Adams attends the premiere of 'Big Daddy' in 1999. Getty Images.

The focus should remain on simplicity with a clean silhouette, minimal detailing and fluid fabrics like silk or satin.

While monochrome tones still feel the most timeless, newer iterations have been seen in sky blue, baby pink and lime green.

 Iris Apatow
Iris Apatow in 2026. Getty Images.

Worn under an oversized blazer or paired with a lightweight knit and ballet flats, Boutaric says the slip dress becomes the staple white t-shirt of dresses.

2. The double-breasted blazer

While the tailored boxy blazer has been a wardrobe staple for years now, the Nineties is bringing back a double-breasted version of it.

Seen across recent runway collections from Prada to Jil Sander, the silhouette has moved towards something more refined, with bigger shoulders and more buttons.

Robb says that when working with simple pieces, proportion becomes everything. "A blazer can make or break the outfit," she says, "it should look effortless, but never accidental."

To make it look more chic, Robb says to pair the double-breasted blazer with straight-leg jeans or tailored trousers in the same material, with block-heeled sandals and minimal jewellery.

3. The white shirt

The white button-down shirt has always been a wardrobe staple, but its latest revival comes in a cooler, more louche take.

Carolyn Bessette-Kennedy famously styled an oversized men's white shirt with a column pencil skirt and gold bag in 1999
Carolyn Bessette-Kennedy famously styled an oversized men's white shirt with a column pencil skirt and gold bag in 1999 (Alamy/PA)

"It works best when you take it away from anything too corporate," says Robb. For example, try not to pair it with a blazer.

"Choose something slightly oversized, worn open at the neck, maybe paired with a sleek skirt or relaxed trousers," she says, a la Bessette-Kennedy.

Robb says to push the sleeves up and loosely tuck the hem so the overall look feels effortlessly undone.

Boutaric describes it as part of a wider move towards "quality basics" – a movement that invests in pieces that can be styled in multiple ways.

Gili Biegun at Paris Fashion Week on 7 March, 2026
Gili Biegun at Paris Fashion Week on 7 March, 2026

Whether worn with slim trousers or blue denim, the white shirt remains one of the most versatile pieces from the Nineties.

4. The clean-cut low-rise

Low-rise trousers have slowly been threatening their comeback for several seasons now, with only a few hopping on the trend with ultra-baggy low-rise jeans.

British singer and actress Billie Piper, wearing a grey macrame singlet over a white bra top and jeans, United States, 1999. (Photo by Vinnie Zuffante/Getty Images)
Billie Piper in 1999. Getty Images.

But this season, the silhouette is taking a more mature turn in tailored cuts, subtle flares and cleaner lines, as demonstrated on Demna’s Gucci runway at Milan Fashion Week in March.

Robb warns against going too literal when wearing this trend. "The mistake is [when people] try to recreate the Nineties exactly," she says. "The moment it feels like a full throwback, it loses its edge."

Dana Smith at Paris Fashion Week on 5 March, 2026
Dana Smith at Paris Fashion Week on 5 March, 2026

Instead, low-rise styles work best when balanced with more current pieces like a fine slim-knit over layered tanks or an asymmetric blazer over a simple sleeveless roll-neck. As Robb notes, low-rise doesn’t have to mean baring your midriff.

5. The everyday clutch

While Bessette-Kennedy’s headband and skinny sunglasses have been making waves, the biggest accessories trend to come back is the casual clutch bag.

On runways from Victoria Beckham to Celine, oversized leather and suede clutches were carried bundled under the arm, creating a sense of business-smart to otherwise simple and pared-back outfits.

BERLIN, GERMANY - MARCH 24: Berna Bilbey in Berlin, Germany.
Berna Bilbey in Berlin, Germany in 2026. Getty Images.

The appeal lies in their simplicity. Without straps or excess hardware, they align perfectly with the Nineties’ minimalist focus on clean, uninterrupted lines.

Boutaric notes that accessories play a key role in elevating these pared-back looks. "Refined and simple [bags] make all the difference."

Whether paired with tailoring or casual denim, the clutch adds structure and intention to an outfit without overpowering it.

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