Christa D'Souza

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Look inside your wardrobe. Do you, like me, have a good few pairs of mismatched high boots stuffed way in the back that haven’t seen the light of day in years? Well if you do, it’s time to drag them out. Or better still, replace them. Thanks mostly to Hedi Slimane at Celine, but also Isabel Marant, Fendi and Victoria Beckham, we should be wearing pretty much nothing else on our feet this autumn. At Net-a-porter, sales of knee-high boots have more than doubled since last year, and it has 80 styles on offer this season, ranging from slouchy to equestrian-inspired.

How, though, to wear them without a) them looking like “f***-me boots”, as we used to call them at college, or b) coming off as a wannabe Sloane? (I’m thinking of the Duchess of Cambridge wearing LK Bennett.)

My first pair? Those would be the tight red plastic patent ones from Miss Selfridge that I persuaded my mum to let me have aged 11 — the “boot” part cleverly detached so you could also wear them as shoes. Six-ish years later, I got myself a pair of baggy boots and, just like everyone else at school, wore them with fluorescent wool legwarmers over the top. In the Noughties, after a seminal sighting of Elle Macpherson in a Chanel pair worn over jeans, I immediately copied the look, but never quite nailed it. Do you need Elle Macpherson-proportioned legs to carry off that haute biker look? You probably do, but that doesn’t stop me from trying.

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That’s the thing about knee-high boots. At point of purchase, they tick so many boxes — they hide ankles that swell towards the end of an evening, cut the cost of pedicures, are more comfortable than regular shoes — but when I actually put them on to go out, they always feel like such a statement. As with hats, they lack equivocality. This is especially true, I find, of those that go over the knee, Ariana Grande-style. How does one do it without looking a little like a musketeer or an angler?

 

The 1970s through to the early 1980s was very much the era of the high boot. Those of you who are old enough will remember a certain look — equestrian accessories, silk scarves round the neck, pleated midis or even culottes, all perfectly exemplified by the Celine of then. It’s that Saint-Germain, Parisian-bourgeois vibe that Slimane has replicated, and it’s a good way to do it, say, for the office or if, like me, you’re d’un certain age. Doing them in a “grown-up way” can backfire, though, if you’re not careful. I give you Theresa May and Sarah Palin as examples.

 

Pandora Sykes, writer and podcast host, is a loyal fan, however. “Knee boots might be trendy again — I long for a glossy, supple pair by Gianvito Rossi — but the brilliant thing about them is that they’re never really not trendy,” she says. “I can’t think of an autumn where I haven’t pulled out a pair of vintage black leather knee-high boots or my patent red ones from By Malene Birger. I love them with both minidresses and maxidresses.”

 

The trick, obviously, is to get one’s references right. Less Waity Katie, then, more Kate Moss. Less Allen Jones (or indeed Bulle Ogier in Barbet Schroeder’s 1976 kink-fest Maîtresse), more Claudia Schiffer on the school run in a check blazer with her skinny jeans tucked in. Or maybe Alessandra Ambrosio at Burning Man, or indeed, Sienna Miller at Glasto. Early Noughties boho — that’s very now, too.

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This season Victoria Beckham did them teetering and skintight with bare toes (still need to do the pedicure, then) or with bows — although as a sturdy-legged friend who can’t get most boots over her calves points out, no one wants their legs to end up looking like two sausages. For most, the best way to do it might be Isabel Marant-style: that is, over the knee, with a ruched dress belted at the waist, showing just a few demure inches of (preferably tanned) flesh. Remember, though, the boot still needs to be loose. A big ask, frankly, once one reaches the inner-thigh-collapsing age of 50.

 

While the point about boots is their utility — their capacity to protect one’s legs from the elements, or perhaps the male gaze — that is of course why they play so perfectly into kinky fantasy, the hint of forbidden flesh peeking out between boot and skirt. But then, wasn’t that the implicit rule for society orgies during the 1960s? Naked, yes, but always shod, and preferably in boots.

 

The other way to obviate the kink is to do it combat-style, as seen on the Prada catwalk. (They come in black, pink and red, with the added functionality of strap-on mini purses.) But again, if you are neither the achingly cool teen singer Billie Eilish nor the Euphoria waif Hunter Schafer, this can be a difficult look to pull off without seeming slightly mad. Maybe the most flattering option is with a pencil skirt or simple A-line silhouette, as shown on the Fendi runway: tight-ish, high and maybe embellished for the evening.

 

The trend for keeping ankles, calves, knees and lower thighs from view, is not going away. Meanwhile, the baggy Loeffler Randall pair that I borrowed for the purposes of this piece garnered no odd looks whatsoever. I wore them, despite the muggy weather, with a £35 crepe cheongsam from Asos. Result. Emboldened, I channelled their Noughties iteration and tried them with a pair of skinny jeans … and probably shouldn’t have. Oof. Madonna/whore, Sloane/slut, stormtrooper/reader’s wife — there is a happy medium, but as yet, I don’t think I’ve quite worked it out.