What shoes do women want men to wear – and do they have to hurt?

What to wear on his feet has always mystified the Times columnist. Time to learn the fine art of shoe shopping

Last week a woman friend told me of how she had once had a fling with a chap, and very nice it was too. But on meeting him for a second tryst, she had found herself repelled – by his shoes. “What was wrong with them?” I asked. “They were too small,” she replied. “Too dainty and fiddly, and he was a tall man.” So what had happened? “Well I was there, so I went through with it that night,” she said. “But immediately afterwards I dropped him.” “Because of his shoes?” I asked, incredulously. “Because of his shoes.”

I wish I could tell you that hers was a lone brutality. It wouldn’t be true. All she was doing was confirming some fears that had begun to take root in me in the past couple of years when noticing comments and asides in various things women had written. It added up to the strong possibility that women care about what men wear on their feet, even when men don’t.

If this was true, then I had a problem that I can best illustrate by analogy. There are dear friends of mine who have no sense of humour. You can see them scanning faces when a joke is being told, then smiling or laughing at as near to the appropriate point as they can – but almost always with a lag. They don’t really get it, and that’s how I am, and have always been, with shoes. I really have no sense of shoe-mer.

Many men don’t or, worse, think they do and don’t. With me, my cluelessness means pedal conservatism, but with other chaps it leads to terrible error. Men are being judged, found guilty of wardrobe crimes and dumped without knowing why. So I decided to help my fellow man and investigate, beginning with a day in Selfridges with The Times Magazine’s deputy fashion editor, Jane Taylor-Hayhurst.

Jane is a Liverpudlian who cannot help but betray her feelings when asked to react to a dress, a haircut or a shoe. We sipped coffee together in Selfridges’ basement. “It’s not just shoes, it’s a personality,” said Jane. “You’d never see Daniel Craig in a sad pair of shoes. I’m not sure about Gary Lineker.” She recalled what her husband wore on their first date: sandy-coloured hiking boots. I told her that this is what I often wear. She moved swiftly on. “Guys’ shoes always just used to be men’s shoes. My nan probably didn’t have an opinion about my grandad’s shoes. But that’s changed.” What did she think of my black shoes? “Safe.”

A man walked past, towards the electrical department. What did she think of his shoes? “Squared-off toes. Ugh! It says he’s a City type who’d probably give you an STD.” You can tell this from his shoes? “Yeah. Definitely. Sexual predator. The wrong kind of womaniser.”

See what I mean? And for square toes among you, I asked a dozen women of different ages the same question and got the same astonishing response. Anyway, up we went to men’s shoes on the first floor, where there was a static parade of male footwear, and Jane took me through the various styles.

There were strange faddy shoes, shoes I wouldn’t know which end to put my foot into, and good old staples, such as the elasticated Chelsea boots that I have never worn. And crepe-soled boots, a version of which I used to love as “desert boots” when a teenager, but which I’d long ago given up on, assuming they were regarded simply as brothel creepers – the forerunner, I supposed, of the square-toed shoe. But no. Jane told me that these were fine, but possibly not with red laces.

Not fine were several pairs with a pre-aged look, seeming as though they’d been caught in a violent thunderstorm, consigned to an attic in 1948, dried out by the central heating and rediscovered on Grandad’s death. And then priced at more than 500 quid.

On we whirled. Trainers were fine on certain men (ie, young ones) and at certain times, but they have to be the right kind. Jane said I could get away with fur-lined black dock boots in winter (like returning your foot to the womb) but that brown Uggs were a vile idea.

We arrived at Jane’s favourites: classic brogues in white, red-brown and light brown – items I have always thought bank-managerly. These were shoe-shoes, according to Jane, made by shoemakers and not by labelled clothes designers. Most of all she praised the ones by Trickers, Prince Charles’s shoemakers. But these were expensive – around £250. So what you do is have two pairs, look after them, resole them, and keep them for years.

Then the next surprise. She was having a love moment with the light browns when I told her that the problem was that my suits are navy or grey. “You can wear these with either,” she told me. There was an intake of breath – mine – because we were in perilous but exciting territory. My daughters don’t call me “Dangerous Dave” for nothing. Brown with navy! Next stop: winkle-pickers!

Absolutely not. Winkle-pickers were for the man who is “clueless, but thinks he isn’t” or “trying too hard”. Then there was “stuck in the past” (moccasins) or “too European” (signature loafers). We concurred on anything with tassels or things hanging off, such as a pair of black Dior belted boots. “Over-designed,” said Jane. “There’s just too much going on there.”

Our own disagreement came over penny loafers. I thought they all looked effeminate and exhibited too much sock. Jane was with the New York mayor, Michael Bloomberg, who alternates two old pairs of loafers.

Outside, newly informed and aware, I found myself looking at everyone’s shoes. All that downward gazing must have made me seem depressed. That afternoon I took part in a panel discussion in which one man, a millionaire formerly in the fashion industry, was resplendent in grey pinstripe and a pair of laceless turquoise trainers. The women around me thought these were fabulous, while concurring in general with Jane’s judgments.

I told them about my woman friend’s story. “Oh, yeah,” said one. “I’ve heard that lots. Girl in a guy’s bed, wakes up in the morning, sees his shoes, and she’s off, never to return.”

Next day I put the problem to an informal panel of male American psychoanalysts. “Ah, yes,” said one. “When a woman looks at a man’s shoes she’s trying to find out what kind of woman he is.” “Come on,” said another. “Foot in the shoe? Penis in the vagina?”

Actually, now, acme of elegance that I have become, I rather accept this explanation. All the things the women told me, they amounted to believing that a man’s shoes say something about his confidence. They want quiet strength that needn’t be flaunted. Maybe Mills & Boon should go into footwear.

What she wants: why Hilary Rose would never fall for an Ugg man

You think you don’t really care about men’s shoes until they get it wrong. Then you realise that you care very much. So to all the men with steel-capped heels: what’s that about? You are clearly a spiv who works in advertising. Please leave by the nearest exit. We will draw a veil over men in Uggs because it’s too upsetting to think about, let alone write about. Studded driving shoes look wrong on anyone north of Milan, and cowboy boots should only be worn by cowboys.

Men’s shoes should look as if you haven’t put any thought into them, as if they just happened and, ooh, aren’t you casually stylish? High-end designer brands look as if you’re trying too hard because they are, by definition, over-designed: you’re paying for something that screams “Prada!” Don’t get me wrong, we’d love you in a Prada shirt, or a coat, but not footwear. What we’re aiming for here is a classic, understated shoe or, even better, a Chelsea boot.

There is something very wrong with a man in a very pointy shoe, or a square-toed shoe, or one of those hideous shoes with a strap over the front and a big buckle, or anything that looks as if it could be worn by Flavio Briatore.

Any shoe that looks like it might attract favourable attention in Hoxton Square – directional, colourful or, heaven forfend, witty – is absolutely to be avoided. Suede is fine, loafers are not, and I assume that anyone who buys tasselled loafers doesn’t care if they never get laid again.

In the interests of research, I looked at the shoes of the men in this office. There are no tasselled loafers, so we can infer from that what we will, but there was a surprising amount of variety, much of it ill-advised, a lot of it brown, and all of them were dirty – brogues, trainers, crepe-soled monstrosities, one pair of Chelsea boots… Only in the management corner do they turn black and plain or, at most, a discreet brogue.

Let me be clear: crepe-soled is an abomination – I don’t care if they’re comfortable and rainproof, and nor should you. Comfortable and rainproof ain’t sexy. We don’t wear clothes just to keep us warm and dry, and we shouldn’t wear shoes simply for the same reason.