Once upon a time, Christmas shopping meant grabbing the newest album release or an old-favourite DVD box set, wrapping it in glitter paper, depositing it under the tree and putting your feet up with a highlighter pen to annotate the Radio Times. Now that music and film lives in the cloud, we’ve turned to clothes as the new go-to gift. But choosing them for another person is a high-risk endeavour. How can we boost our chances of getting it right?
Because we do really, really want to get it right. Kids just want Santa to bring them the swag, but one of the things that happens when you become a grownup is that you care more about whether other people like the gifts you’ve given them than you do about what you receive. And fashion is more difficult to get right than many think. After all, if how to dress well was self-evident, then I wouldn’t have a job.
Actually I take that back. If money were no object, then fashion gifting would indeed be simple. Next to no one would be disappointed to find a Dior handbag or diamond earrings under the tree. But that’s not the reality of Christmas shopping for most people. The search for desirable, appropriate gifts within budget constraints is hard work.
Not to mention the fact that you are trying to tick 10 people off the list in the 90 minutes you’ve got free before you have to leave for the carol service. So I will cut to the chase with my pointers for successful fashion gifting.
First, the basics. If you are buying clothes for someone else, stick to pieces that don’t really need to be tried on. This is why socks and ties are hardy perennials. But this category also includes most jumpers, jewellery and tights. Do not even think about jeans or a dress. Narrowing the categories down in this way will make shopping easier: decision fatigue is real.

Secondly: do not buy anything for someone else because you think it’s funny. Gift giving should always be about the recipient, not the giver, and it seems to me that the point of hilarious gifts (which are never actually hilarious anyway) is usually to showcase the wit of the gift-giver. If you must give an amusing gift, it has to be a joke that casts the recipient in a flattering light. A baseball cap with a smart, in-the-know funny phrase is fine (if they are a cap wearer), pyjamas with “Beware, Not a Morning Person” are not. Relatedly, avoid Christmas-themed socks, pyjamas or anything else. These might feel festive in the moment, but by Boxing Day they have all the magic of leftover sprouts.
Do you know this person’s taste, or just their style? I was recently introduced to this distinction, and I find it to be helpful in figuring out how confident I am that a gift will be well received. Taste and style are not the same. Your style is the mode in which you present to the world; your taste is what you consider beautiful. If you know someone really well, and are confident you understand their taste as well as their style, then you can be bold in your pick. But if you’ve never been inside someone’s home, you might know their style, but you don’t necessarily know their taste.
Instead, stick to slightly different versions of pieces you have seen them wear. Do they like a contrasting scarf with a coat? Do they always belt their jeans? Do they wear hoop earrings? Don’t overthink it: pick something you are confident they will use. To play it safe, work within categories that are worn at home (a dressing gown) or outside (wellies, gloves) rather than those where sartorial standards are tougher and more complicated, like work or party wear. Monogramming their initials is a smart way to make a simple, no-fail present (a fluffy white robe, for example) feel special.
Oh, and one last thing. You know what always goes down well? Tucking in the receipt. Not that I don’t back you to get it right. But this game is harder than it looks.
Model: Imogen May at Milk. Hair and makeup: Sophie Higginson using Davines and Reome. Knit, £35.99, Zara. Skirt, £46, Marks and Spencer. Tights, £23, Falke

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