Time to retire the office trainers: grownup shoes are back

There is a saying that goes: you can judge a man by his shoes. Actually, that’s not true, there isn’t. The original proverb actually advises that you shouldn’t judge a man before you have walked a mile in his shoes. Which is almost the opposite, when you think about it, since it is counselling against snap judgments rather than in favour of them. Also, not really about shoes.
Both sayings – the real one and my version – are wise in their own way. Not passing judgment on a person until you have walked in his shoes – climbed into his skin and walked around in it, as Atticus puts it to Scout – is kind of entry-level humanity, really. But the idea that you can judge a man by his shoes also has a nugget of truth in it, if you swap the word judge (bit judgy) for the word read. You can read a person by their shoes, because shoes are where we give ourselves away. Not because shoes are deep and meaningful, but because shoes are practical. Shoes are where your outfit gets real. They have to work. They are quite literally down to earth.
Your shoes reveal your intentions and communicate them to the world. Sometimes in obvious ways (if you see someone putting wellies on, you can pretty much assume they are heading outdoors) and sometimes in more subtle ways. When you put on your highest, most teetering heels, you send a signal to the world that this is a day or evening you are prepared to put some effort into, and that you might not be up for a long walk home or getting the night bus.
Right now, grownup shoes are the key to nailing fashion’s vibe. Loafers, court shoes and slingbacks have taken over from trainers, Crocs and jellies. This is an attitude, as much as an aesthetic. Fashion is getting a little more sophisticated, a little less silly. And that starts with shoes.
These days, if I look in the mirror and feel like I can see a shadow of Cary Grant or Diane Keaton – the soft billow of a proper pair of trousers, a good shirt, possibly a waistcoat – that makes me happy. I don’t know quite how or when or why Grant and Keaton affixed themselves to my internal mood board, but I am pleased they have, because they bring a mood of low-key confidence – not so much swagger as unflappability – that feels good.
Loafers are the perfect partner for proper trousers. You need something solid to ground the silhouette, but trainers feel too glaringly modern and make the silhouette feel too rounded, as if you’ve got dressed in bubble writing. Gucci are the OG here, of course, but I’m almost as fond of my trusty Russell & Bromley pair, which have lasted four years and counting. Boden are also excellent for an affordable loafer.
A midi skirt with flat white trainers remains a classic working-wardrobe formula, with one such woman on every rush-hour train carriage. If this is you and you are in the market for an update, can I suggest a low-heeled pump with an almond-shaped toe? You only need a teeny-tiny heel, so you can still do the school run, but now you can pretend you are wearing The Row. It will make your life much better – trust me, I do it all the time.
The best part about the new grownup shoe is that this isn’t about balancing on a stiletto. We’re talking 5cm, max. A low-heeled slingback is a genius choice for comfort – you’ve got a stretchy strap, which gives a tiny but crucial flex in sizing so you don’t get any heel rubbing. Perfect – and very grownup – with the elegantly simple Jean Shrimpton meets Jackie O dresses that are around this season.
Cool French-girl brand Sézane is brilliant at low-heeled shoes, which it calls “Babies”, as in baby heels. I can vouch for the slingback, low-heeled Paula Babies (£160), which I have in a shiny caramel colour. They are grownup without being boring – and divinely comfortable. Because the shoes you really need to be able to walk in are your own. Is there a proverb for that?
Stylist’s assistant: Sam Deaman. Model: Maria Diniz at Milk. Jeans, £27.99, Zara. Sheer socks, £11, Falke. Shoes, £195, Bobbies