Does your brother or sister pride his or herself on knowing that band you haven’t heard of? You know, the one they’ll deny liking when they’re wildly mass and popular? Do they see advance screenings of indie films? Have they been stopped for street-style shots?

If you answered yes to any of the above, then you’ve got the classic too-cool-for-school sib. Don’t worry, I have one, too, and they’re nearly impossible to shop for. So as somebody with a little experience, let me guide you through gifting them for the holidays.

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Keel's Simple Diary 2

Keel's Simple Diary 2, $15 from TASCHEN Books
Some people think diaries are lame, but these ones are super-funky-fresh. The Simple Diary takes the stress out of keeping a journal. Each page boasts a different quiz—because sometimes staring at a blank diary can be very daunting.