Most people are pretty terrible gift givers (including me). We tend toward generic gifts so that the recipient will at least use the gift, albeit probably not like it. If we continue down this path, everyone will be exchanging tooth brushes in about 20 years.
The only real key to giving a gift is making it thoughtful. Everybody loves when the gift has some kind of personal touch. Even if it's a complete joke, as long as it is geared the personality of the person, its better than an AmEx gift card that they will forget you even gave. I once received a series of hand drawn cartoons that depicted various activities I was good at - I still have them to this day and remember who gave them to me.
If you can't think of something good, at least don't give something bad. Here are some common mistakes:
1. A DVD. We know you got it out of the bin of $5 DVDs at Best Buy. Who wants some 3 year old mediocre movie? I can rent this any time on any number of different devices. But you know what? I don't. Because I don't care about this movie. Why would I want it taking up space in my home? I actually don't even have a method of watching DVDs anymore. Welcome to 2013 - we watch movies in the cloud. If you are buying a DVD - it better be collector's edition or have some special meaning that the person will really like.
2. An iTunes Gift Card. I have given and received this one several times. It just seemed so easy. Well it was easy - but also boring and also 3 years ago. There are so many legal ways to listen to music now (I currently use Spotify, it's amazing). I don't know many people buying music on iTunes. Don't send me backwards in time with the most generic gift of the 2000s.
3. Clothes that are the Wrong Size. I strongly dislike getting a shirt or pants and having to then take them to get tailored or exchange them. You are basically giving me a chore for the holidays. It isn't too difficult to figure out my size - put in a tiny bit of effort. If its a bit off because you got a different brand, no shame in that. At least you tried. Just don't guess, give and assume the person can return it.
4. Wine. You are undoubtedly going to need some hostess gifts or gifts for people you don't know so well. I can't stand when people say "its always safe to bring wine." I say, its always a disaster to bring wine. A couple things can happen: (i) Your bottle gets lost with the bottles other people brought and your gift becomes insignificant in any way. (ii) They have way better / more expensive taste than you. They don't want your sh*tty bottle of wine. (iii) They don't drink. (iv) It gets re-gifted. (v) You drink your gift - which makes it not a gift at all. Does this person like food? Like cooking? Try olive oil - makes a neat gift and shows you know they like cooking. (www.puremountainoliveoil.com)
5. A Destination T-Shirt. It is tempting (and easy) for you to pick up a shirt from the tourist shop on your latest vacation. Although it is a thoughtful gift, I have drawers full of the standard t-shirts. A lot of times I get these shirts for free (from sporting events, volunteer events, etc,) which results in piles of the same type of shirt, just with different designs on the front. I typically wear them around the house or to go to the gym. So what once was a somewhat thoughtful purchase turns into a dirty gym shirt or rag. Not quite a memorable or lasting gift by any standards.
Good Gift Ideas (Other than BeltCraft belts!):