Are you still wearing well-worn Wellington boots or have you graduated to Ons?

They say you can tell a lot about a man by the shoes that he wears. It’s an old cliché, but clichés have a habit of sticking around for a reason: they tend to be true. Long before he even opens his mouth, you’ve already got a pretty good idea of who a man is by his choice of footwear: practical or flashy, traditional or trend-led, the sort to disappear for a 10k run before breakfast or spend Saturday mornings reading the papers.

More than almost anything else in a wardrobe, shoes are a dead giveaway. They tell a story about who we are — or, perhaps more importantly, who we’d like everyone else to think we are.

Wellington boots

If your favourite shoes are a pair of wellies, you’re probably the sort of person who believes almost everything in life is better when it’s properly made. You’ll happily spend more on something if it means never having to replace it, whether that’s a wax jacket, a pocket knife or the right footwear for a country lane.

You have little patience for disposable culture and even less for people who complain about the weather. To you, rain isn’t an inconvenience: it’s simply a reason to wear the right shoes.

You’re practical without being preachy. Friends know you’ll always have a torch in the car, an umbrella by the door and the number of someone who can fix almost anything. As everyone else tiptoes around muddy puddles, you march straight through them without a second thought. Secretly, you rather enjoy those days when the weather is bad enough to justify wearing your favourite pair.

Oxfords

If your favourite shoes are a pair of Oxfords, you’re not interested in making an entrance. You’d much rather make a good impression. You subscribe to the idea that if something has worked for the past 100 years, it’s probably worth sticking with.

You don’t need your shoes to start conversations, because you’re confident that the rest of you will do that just fine. You are the sort of man who irons his shirts properly, arrives when he says he will and hangs his coat up rather than throwing it over the back of a chair.

When you find a good butcher, barber or bottle of claret, you see no reason to look elsewhere. Loyalty counts for something, and so does consistency. Friends occasionally accuse you of being set in your ways, but you prefer to think of it as knowing what you like. As people out there wonder whether burgundy is the new brown, you’re happily wearing shoes that looked smart when your father was your age — and still will when your own son gets there.

Loafers

If your go-to attire involves a pair of loafers, you believe that dressing well should involve a little showing off. In fact, you think that making an effort is a sign of respect, whether you’re heading off to a wedding, settling in for a long lunch or simply meeting friends at the pub. When everyone else is debating whether trainers go with tailoring, you’ve already slipped into your loafers and moved on with your day.

You have a healthy appreciation for the finer things, but are not interested in shouting about them. You know a good martini should be cold, linen should be slightly creased and holidays are always better somewhere that serves lunch outside. You probably own at least one pair of sunglasses that people describe as ‘a bit much’ — and take it as a compliment.”

Whether worn sockless in July or with a chunky knit when the weather turns, loafers tend to suggest someone who is comfortable in their skin; the sort of man who knows that style isn’t about following the rules. Rather, they make him look as if he was never worried about them in the first place.

Sprinters

If your preferred shoes are a pair of Sprinters, you realise that looking interesting is far more important than looking rich. You’d rather someone asked you where your trainers came from than how much they cost — and are perfectly happy if only one person in the room recognises them. To boot, you’d probably prefer it that way.

You are endlessly curious, too: weekends are spent wandering around vintage shops and exhibitions of which half your friends have never heard.

You know the best coffee is usually found where nobody else is looking and are convinced that the best clothes all have a story behind them. Trends are not for you to chase, but to stay one step ahead of. By the time everyone else has discovered something, you’ve already moved on. It may seem a touch obsessive — yes, you’ve been known to discuss hems and silhouettes at dinner — but your enthusiasm is infectious. Your favourite shoes say you’re a collector of ideas as much as artefacts.

On trainers

Perhaps no shoe has enjoyed quite the same ascent as the On trainer these past few years. So it is that we must dedicate an entire segment to it alone; if your favourite shoes are a pair of Ons, there is a good chance you’ve already been up for an hour by the time everyone else is reaching for the snooze button.

You’ve got a preferred running route, a favourite recovery drink and an opinion on foam midsoles that nobody actually asked for. You don’t ‘go for a jog’: you are training for a marathon and everyone must know about it.

You love efficiency. Your watch tells you how well you slept, your shopping arrives on a subscription and your calendar is laid out with little colour-coded categories. Secretly, you quite enjoy hearing people complain that they are too busy to exercise. Not because you’re smug (well, not entirely), but because you know they’d feel better if they simply came with you.

We’re stereotyping, of course. Plenty of On trainer-wearers simply appreciate a sneaker that’s comfortable enough for walking the dog, dashing through Terminal 5 or spending a day on their feet. Even then, your favourite shoe suggests someone who enjoys when life runs smoothly. Organised, dependable and always prepared, you are the living embodiment of the time-old adage: ‘If you want something done well, ask a busy person.’

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This feature originally appeared in the November 4, 2026, issue of Country Life.