I just posted about The Most Important Thing I’ve Learned About Negotiation — that you and the other party can create value by finding things that are relatively easy for you to give up and relatively valuable for them to have. For example I could find a teenager and trade an edit of their college application essay for an afternoon of running errands — I’m a fast editor and they have plenty of time.
The same lesson applies to finding meaningful gifts. If the person you’re buying for is short on cash, then you could simply imagine all the things they would like to have but can’t buy and pick one of the list, or just buy them a giftcard. But if your giftee can buy themselves whatever they really want, then consider what you have that’s special that would make the other person happy and that they would have trouble getting on their own.
For example, when my mother wanted to put in wood floors, I researched all the different options from laminate to a variety of real woods, and made her an organized binder of info. In an office secret santa event, a coworker who was married to a La Mer employee gave a jar of their moisturizer that was probably worth $100, but that she had gotten very cheaply.
Finding a way to combine your personal skills or resources to meet one of your giftee’s desires will make the best kind of gift. Maybe you are crafty and can knit a unique hat. If you can cook, and the giftee can’t, cook them dinner. If you know a lot about art, give them a personalized tour of a museum. If you’re a fashion expert, buy them a shirt that they wouldn’t have thought to choose but that perfectly matches their wardrobe.