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How to wear flares without looking like a noughties Britney Spears

The fashion industry is determined to bring back flares. But for those of us who spent the 00s in bootcuts, the silhouette can feel decidedly dated. How do you style them without channelling late-Spice-Girls-era Victoria Beckham? It’s all about the details.

SHOES: stacked heel not pointy shoe

This picture of Kate Moss was taken in 2006, but could be on your mood board for now. And that’s Jennifer Aniston in 1999. It’s not just the presence of Brad Pitt that dates this picture

We lost count of how many times Jennifer Aniston wore pointy pumps and bootleg trousers in the 90s. Avoid this at all costs. Shoes are one place where it’s OK to borrow from that other flare era, the 70s. Stacked platform sandals and flared denim is a classic look, a bit Mary Ann from Tales of the City mixed with Kate Moss. And that can never be a bad thing.

WAISTLINE: high-waisted not hipster

Though she was a repeat bootcut offender in the 00s, Victoria Beckham wears flares the modern way, with a high waist, in 2013. Britney Spears shows her abs in 2001.
Photograph: Corbis/Rex

Britney’s favourite look in the early 00s consisted of a top that finished just below the bellybutton and flares that began just above the pubic bone, exposing – at a guess – 15cm of bare midriff at all times. 2015’s look is not about skin, so high-waisted flares are the only ones that cut it. The proportions make sense – a higher waist will make your legs look longer. See: VB.

TOP: Prince not Jane Birkin

What a choice. Prince at the Grammys in 2015 v Jane Birkin in 1974.
Photograph: Getty/REX

We’ll always heart Jane, but her cropped T-shirt and flares look is best left in its lovely 70s-in-the-south-of-France moment. Instead, look to Prince at the Grammys in orange flared co-ords. Very cool, very Celine, very now. Cane and afro optional.

LENGTH: ankle length not puddling

Alexa Chung and Heidi Klum. Their names rhyme (sort of), but where ankle-flashing is concerned they find little common ground.
Photograph: AG/Getty

Alexa Chung’s Revolutionary flares – part of the range she designed with AG Jeans – are set to be the fashion insider favourite this season. That’s partly based on the length – they hit just above the ankle. It doesn’t sound much, but it takes it away from that flare no-no, puddling (ie when your trousers are slightly too long) over a pointy shoe. This isn’t an era issue. It is simply a style trope that must stop.

STYLING: half-tucked shirt not pulled-down vest

Vogue’s Sarah Harris with an untucked shirt over jeans in 2014 and Nicole Ritchie in 2004.

Bootcut trousers are much loved by womankind for their flattering qualities – the wider leg makes thighs look slimmer, and wearing them with a vest shows off an abs exercise routine. But didn’t you get the memo? 2015 fashion is not about being attractive, it’s about being interesting. See the half-tucked tunic shirt: this street-style styling staple turns your look from Californian juice drinker to nonchalant fashion editor on the streets of Milan.

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