How to buy clothes for someone whose style you don't understand

There is a particular species of gift failure where the recipient says 'oh, that's lovely' in a very specific tone. It is almost never that the item was bad. It was that it was bought for a version of them that exists in your head.

Both halves of that are solvable without ruining the surprise.

The size problem: stop guessing, go and look

You do not need to ask anyone their size. You need four minutes alone with their wardrobe and a phone camera.

1. 01Find three pieces of the category you are buying — three jumpers, three pairs of jeans — that you have actually seen them wear a lot.
2. 02Photograph the care label of each. That gives you both the size and the brand.
3. 03If the sizes disagree, that is information rather than a problem: it tells you which brands they size up in.
4. 04Lay the best-fitting one flat and photograph it next to a tape measure, pit-to-pit. Two numbers beat any size label.

The reason the label alone is not enough is that a size is not a measurement — brands set their sizes independently against their own fit models, so a medium in one is not a medium in another. If the three labels you photographed say S, M and M, buy the brand whose label said M.

The taste problem: buy what they wear, not what you'd like them in

This is the harder half and the one people get wrong more confidently. The instinct when buying clothes for someone is to buy something that would improve them — a brighter colour, a sharper cut, a step outside their usual. That instinct is the single largest source of unworn gifts.

The correction is unglamorous: buy the thing they already wear, in a better version. If they live in grey crewnecks, the gift is an excellent grey crewneck, not the interesting green one. Their taste is not a problem you were asked to fix.

• Look at what is worn out. The most-worn item in a wardrobe is the clearest statement of preference anyone makes.
• Look at what is folded versus hanging. People hang the clothes they think they should wear and fold the ones they actually do.
• Count the colours. Most people wear four. Buy inside them.
• Note the silhouette, not the item. Someone who wears everything oversized will not wear a fitted version of the same thing.

If you want the framework for naming what you are seeing, the ten style tribes breaks each look down into silhouette, palette, fabric and polish — which is a much more useful thing to hold in your head in a shop than 'they like nice things'.

The bit that used to be impossible

Even with the size right and the taste right, there is a third failure: the piece simply does not suit them. Their colouring, their proportions, the way they carry their shoulders. You can only find this out after they open it, and by then everyone is committed to being pleased.

This is the thing that has genuinely changed. You can put a garment on a photo of them — a friend, a partner, a parent — and look at it before you spend anything. It takes about a minute, and it converts the entire exercise from a guess into a decision.

Practically, that means you can compare four coats on the actual person rather than four coats on a studio model, and pick the one that works. It also means you can find out that the shape you were sure about is wrong for them, which is worth more than any of the four.

The rules, condensed

One argument for doing the opposite

Everything above optimises for the gift being worn. There is a separate, legitimate thing you can do with clothes and another person, which is to put them in something ridiculous entirely for the joke — the fur coat, the full tuxedo, the outfit they would never in their life buy — and send it to them.

That is not a gift and it is not shopping, and it is genuinely one of the best things you can do with a try-on. Nobody has to wear anything. The picture is the point.

Put the coat on them before you buy it. Or put them in the tuxedo, for free.

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