From five-fingered trainers to the shoeless shoe: what’s with all the freaky footwear?

‘Ugly’ shoes, once the preserve of the catwalk, have gone mainstream. Why are so many people taking a walk on the wild side?

Until recently, a busy commuter train would be packed with people wearing low-key, unobtrusive shoes. An elegant and inoffensive pump, a sporty trainer or a polite and basic ballet flat, they were the type of shoes that said background extra rather than main character energy.

But now change is afoot. Deliberately strange designs are reaching new heights of desirability. Polarising rather than pretty, these shoes tend to be flat, a little bit orthopaedic and, according to the internet, “ugly”.

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Lime bike jousts? Why youth culture is embracing the medieval era

From chainmail-wearing pop stars to high-fashion catwalks, the spirit of the middle ages is erupting into the zeitgeist

Medieval knights used to joust on warhorses with wooden lances, but this week in east London, two men jousted on Lime bikes with PVC pipes. This contemporary spin on a medieval spectacle is just one example of the spirit of the middle ages erupting into the zeitgeist.

As part of Frieze art fair, the artist Corbin Shaw staged a show called Feast of Fools. The “‘anti-Frieze” Frieze show took inspiration from a medieval festival where, as Shaw put it to GQ, “the peasant class could insult the rich”. In the video for Troye Sivan’s latest song, Party, the Australian pop star postures as a medieval knight.

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‘A form of anti-status status’ – how much would you pay for a plain tote bag?

The ubiquitous carrier has been given a four-figure makeover. But why has an everyday bag associated with running errands and US supermarkets become so aspirational?

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If you were in the blessed position of having £500 to spend on a bag, what would you look for? Would it be made of cotton? A nice light shade bound to sully quickly, like “paper white” or ecru? Would you want something that looks a lot like those ubiquitous totes sold by a certain US supermarket chain for a couple of dollars?

No, thought not. But there are plenty of options if you do. Phoebe Philo, former Celine designer and quiet luxury pioneer, offers a white canvas shopper, made entirely from cotton except for the silver brass hardware of its internal zipped pocket, for £450. Luxury Swedish brand Toteme’s “effortless tote bag” is made from organic cotton canvas and is available in dark brown, red or classic ecru. It goes for £510. Tom Ford’s version, at £1,600, differentiates itself a little, with a body made exclusively of cotton canvas but trims and handles from calfskin. Prada’s, which features leather details and metal hardware, could be yours for over £2,000.

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‘I wanted to create the female version of a man’s suit’: how Roland Mouret’s Galaxy dress took over the world

One the most famous dresses of this century, it was worn by royalty and A-list celebrities in the noughties. Its latest fans are Maga women. Here, the designer, and former mentor to Victoria Beckham, reveals the story behind it

The story of one of the most photographed and ripped-off dresses of the last 50 years came together with a simple zip. It was 1998; the designer Roland Mouret had shown his first collection at London fashion week and was looking for a way to produce good clothes at speed. He connected with a small British atelier and it was there that some old-school industry wisdom would alter his course: he learned that a longer seam doesn’t actually cost any more than a shorter one.

Despite his brilliantly instinctive approach to design, it was like cracking a code – and steered him towards the dress that would make his name. “My brain was buzzing!” he says. “I hadn’t thought about it before – if you extend a top by 50cm, it becomes a whole outfit. You just need accessories. Focusing on dresses gives you a signature piece at the right price.”

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Jess Cartner-Morley on fashion: don’t want to get your Big Winter Coat out just yet? Try ‘onion dressing’

It’s time to learn the art of layering – and we’re talking a crew neck with a ballet wrap and blazer, not full-on outdoor explorer

Is layering an art? Probably not in the traditional sense. We are not talking the Bayeux tapestry here. No one is going to queue round the block to admire the subtle interplay between your Uniqlo Heattech and your cashmere crewneck. Still, I think it’s nice to romanticise this stuff. The deeply unpoetic truth is that it is going to get cold and wearing one item of clothing at a time simply isn’t going to cut it. So let’s pretend that the sliver of white T-shirt beneath a jumper, the shirt collar poking out above a cardigan, or the ballet wrap over a snug top are not acts of basic thermal self-preservation, but composition. A creative statement about proportion, texture, colour and self-expression. If you have to wear half your wardrobe at once, you may as well make a masterpiece out of it.

The avant-garde layering term to drop in order to sound like a connoisseur this season is onion dressing. Not the most romantic name, but a clear visual for the most refined form of layering, which is fine layers rather than hefty ones. And instead of the top layer covering all beneath it, each piece should be visible. As if we were slicing through the onion and looking at a cross-section if you will excuse me labouring the allium thing. This is layering with finesse rather than brute force. Hems and collars and cuffs give an outfit depth and texture without adding too much bulk. You want to look intriguing and multi-dimensional, not like Joey in Friends wearing all of Chandler’s clothes.

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