Why every generation secretly thinks the one before them had more style

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Why every generation secretly thinks the one before them had more style


Fashion moves in circles. Anyone who’s been wearing clothes for more than a decade or so of their adult life will know this: overnight, that long forgotten pile of hand-me-downs from your mother, or even grandmother, transforms into the season’s most coveted capsule wardrobe. It’s a cycle fuelled by nostalgia, pop culture, and recurring consumer habits.

Now, a team of mathematicians from Northwestern University has claimed that the cycle lasts 20 years, with trends having repeated themselves within that timeframe since 1869. The study was based on an analysis of around 37,000 images of women’s clothing dating from the 19th century to the modern day, noting how trends aligned every two decades. For example, in 1985 and 2005, the key trends were denim jackets, high–waisted jeans, and leg warmers.

We’re seeing the same thing happening in 2026, with some of this season’s key pieces dating back to 2006. This will come as no surprise to anyone with an Instagram account, where photographs of early Noughties It-girls are rife, with the algorithm safely upholding their status as contemporary style behemoths. Think Sienna Miller and her giant buckled belts. Alexa Chung’s skinny jeans. Kate Moss’s entire wardrobe – the model’s cult Topshop collection launched in 2007 and still proves popular on eBay.

It’s no wonder all of the most coveted sartorial sensibilities require us to look back – consider the fashion world’s revived obsession with Carolyn Bessette Kennedy, courtesy of Ryan Murphy’s viral Disney+ drama, Love Story, which documents the Calvin Klein publicist’s courtship with JFK Jr before the couple’s tragic and untimely death in 1999.

So, if you want to be on trend this season, consider this your guide, with the five must-buys to channel that 2006 aesthetic without looking remotely dated.

Capris

Pants suit: Carrie in ‘Sex and the City’ popularised the Capri look (HBO/Asos)

Your go-to trousers for spring are straight out of Carrie Bradshaw’s wardrobe; capri trousers were a staple for the Sex and the City, who often swanned around Manhattan in a pair, styling them with floaty bohemian blouses and Manolo Blahniks. Capri pants were also a standout style in Chanel’s spring-summer 2006 collection, when the French fashion house was helmed by Karl Lagerfeld, who styled them with double-breasted blazers and ankle boots. According to the second hand retailer Vinted, searches for capris are up, with a 406 per cent year-on-year increase on the platform. Reformation, M&S and ASOS all have some excellent options: walk, don’t run.

Ballet flats

Heel? No: flats are back

Heel? No: flats are back (Getty)

All the cool girls were wearing them in the early Noughties – and now, after a brief shift towards clompy, chunky shoes, ballet flats are firmly back in the footwear zeitgeist, with a 221 per cent year-on-year rise on Depop. The trend has taken a surprisingly gender-neutral turn of late – see Harry Styles in mint-green, Dior ballet flats at the Grammys – so there are plenty of options to suit all tastes. We suggest channelling a French sensibility, looking to brands like Sezane and Repetto for a classic, well-made pair of ballet flats to last you all spring and summer long.

Bodycon dresses

The cling’s the thing: SJP sets the trend back in the day

The cling’s the thing: SJP sets the trend back in the day (HBO/Reformation)

No, not the Herve Leger bandage dresses. Think sleeveless, strappy, fitted minidresses that you can just as easily wear to work as for a date. Again, Carrie Bradshaw is a good reference here if you can remember that clingy gunmetal grey dress she wore in an episode starring Justin Theroux. Boutique brand of the moment Gimaguas has some great options, as does Spanish label Paloma Wool. And of course, you can’t go wrong with a Reformation knit dress.

Slouchy bags

Ritchie kid: Nicole modelled a look that still endures

Ritchie kid: Nicole modelled a look that still endures (Getty/& Other Stories)

Gone are the days when backpacks and slick totes were the accessories du jour. Now, the chicest way to carry your laptop, gym gear, and other bits and bobs is in a slouchy shoulder bag, the kind that would often be seen hanging off the shoulders of Nicole Ritchie and Paris Hilton in the early Noughties. According to Depop, slouchy city bags are experiencing a 758 per cent year-on-year search increase. If your purse strings can stretch, Balenciaga’s Le City is the ultimate offering, though we also love the slouchy top-handle bag at M&S, as well as similar options at Free People, & Other Stories, and Strathberry.

Baby tees

A fair crop: Ruby Loot with one of her tees

A fair crop: Ruby Loot with one of her tees (Ruby Loot)

Crop tops were a staple in 2006, with the fashion set almost always pairing theirs with low-waisted True Religion jeans. Now, the trend is back in a very specific way: introducing baby tees, the fitted, cropped T-shirts that can be worn with just about anything, from high-waisted pencil skirts to leggings. With this trend, the more outlandish the better – slogan baby tees are making a particularly big splash on social media, often referencing Britney Spears’ famous “Dump Him” blue baby tee that she wore in 2002. Today, there are variations of this everywhere, from Zoe Kravitz’s go-to brand, Cou Cou Intimates and its viral “Show me your b00ks” t-shirt, to Insta-favourite Ruby Loot, whose wide range of tees feature slogans such as “chronically online” and “too old for DiCaprio”.



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