Is over-the-knee OTT?

On the whole, winter dressing holds none of the pitfalls of summer.

Such pressing quandries as “Can I wear shorts to the office? Can I pull off pastel? Can I do dungarees, period?” are replaced by the resignation that you’ll be spending the next four months wrapped up in a very big coat. Add in a few slouchy jumpers and a pair of black jeans and you’ve got yourself a wardrobe to last the season. Easy.

But there is still one item of clothing that requires a bit more consideration now than at any other time of year — your footwear. Then you’re faced with a long list of requirements. They must be waterproof, cold-proof, slip-proof, all while managing to look half-decent with the aforementioned big coat.

For many, the answer lies in a pair of over-the-knee boots.

On paper, they’re the perfect solution: cosy, sturdy and with more than their fair share of fashion clout. But it’s territory not all dare to tread. They are the exhibitionists of the winter footwear world and, much like a white dress at a wedding, the decision to pull on a pair of thigh-highs is not something to be taken lightly.

But this is one item that is all in the wearing.

“There’s a huge difference between wearing flat over-knee boots and ones with a heel,” says Hannah Rochell, flat-shoe enthusiast and founder of esteemed fashion blog EnBrogue.com. “Heeled tall boots automatically conjure up images of Julia Roberts in Pretty Woman, especially when worn with a short skirt. Flats come without those connotations; they are easier to wear with a skirt or dress without feeling too tarty.”

In other words, the way in which Kate Moss wears hers (flat, obvs, with a black jacket, black tee and black jeans) is a wee bit different to Miley Cyrus (spike-heeled with crotch-length shorts, crop top and graffiti-ed denim jacket). See also Alessandra Ambrosia’s corset-fastened thigh-highs on a racy Chanel photoshoot last month versus Sam Rollinson’s demure Sixties siren look in Kurt Geiger’s latest campaign.

There are a few exceptions to the rule — Miranda Kerr, for example, looks ace in her stiletto-heeled leather pair, teamed with either a short flared skirt or minidress. But we can’t all be Miranda Kerr, and for most it’s safer to keep it simple.

“If in doubt, it’s best just to team both heeled and flat versions with some skinny jeans and a slouchy jumper,” adds Rochell. “That’s how I’ll be wearing mine, at least.”

Hers, in case you were wondering, are a pair of studded black suede versions from made-to-measure British footwear brand DUO. Both Russell & Bromley and Alice Temperley’s Somerset collection for John Lewis have viable options on the high street, while Isabel Marant’s slouch-fit suede versions are at the top of every fashion editor’s winter wishlist.

But simple doesn’t always have to equal safe. If it did, you may as well stick to a nice pair of ankle boots. True, Rita Ora’s white patent look may be best left to Kosovan pop princesses, but Fearne Cotton manages to pull off a pair of crystal-embellished boots nicely, when dressed down with an oversized pink cable-knit jumper.

And then there’s Theresa May. Last week, the Home Secretary stepped out in a natty pair of black crocodile-print patent leather thigh-highs and looked… pretty good. Granted she’s never been one for the standard-issue politician court shoe — see the rhinestone-heeled lace-ups and leopard-print pumps for reference — but even we had to commend this as a brave choice. And in fashion, as in politics, it pays to take risks.