The first thing to do is think about them, their interests and habits. There are almost as many varieties of cool as there are species of beetle on Earth. Is your targeted recipient a fashionista? Are they an indie-band loving hipster? A refined and erudite poet? Once your taxonomy exercise is complete, you’re ready to begin choosing a gift for them. Any time you need to find cool gifts for cool people, it helps to get to know their world a little.

Let’s start with the fashionista. What are his or her favourite designers? Can you raid their closet, not to remove anything, just to read the labels? That’s a good starting point. The next step, once you’ve sussed their sense of style, is to try to extrapolate from there toward something they don’t have that fits your budget. If they have several Fendi bags, and you’re on a schoolteacher’s budget, another Fendi bag might not be the ideal way to go, unless you want your payments on that gift to eclipse your car payments. Consider instead a smaller bauble from Fendi, something within your budget that she’s not likely to have (not being sexist but statistically, handbag owners tend to be female). If you live in a major city, perhaps there’s a designer opening a collection, or runway shows you can take them to. Lastly, if your ambition outstrips your budget (fashion is an expensive passion) then consider getting them a subscription to one of those glossy fashion mags they pick up every month.

Now what about the indie-band-loving hipster? Are your tastes in music cool enough for you to buy them CDs? Possibly you can, but you really, really, really have to know what they like. Musical tastes, even among enthusiasts of the same genre, tend to be idiosyncratic and personal. Get to know theirs if you’re going to go this route. Alternatively, (no pun intended) it’s easier to figure out which is the coolest music shop than which music makes for cool gifts. A gift certificate may be in order. Along those lines, chances are in these de-centralized times, there’s a club near you where bands play the sort of music your hipster loves. Why not a gift certificate for a night out, discovering the next indie band everyone will be talking about in a month or two, in a small, intimate club? Be careful about offering to accompany them, however. If they are younger, than you odds on they’d rather go with their friends.

The poet may be easier than the other two. There’s always poetry. You can check their shelf for their favourite poets, and even if they have the complete works of, say, Stevie Smith, you could always endeavour to find a first edition, or signed edition, for them.