Since I can be a little bossy about telling Sweet Pants which clothes I think he needs to wear, he occasionally forwards me pictures of dresses or sweaters that he thinks would look good on me. But I rarely take his suggestions. For one thing, I never order stuff online because I'm too sure it won't fit right. I will think, Sure, that sweater looks great on the J. Crew girl, but I can never pull off those wide collars. Or, Yes, that aquamarine silk dress is gorgeous but silk always makes me sweat so uncontrollably under the arms that I'll ruin the thing after a couple of wears. There's so much that could go wrong! So many variables! Sizes vary wildly depending on brand, dresses that fit well on top may hang on the bottom (or be too tight at the waist while being too loose around the boobs), and those wacky jodhpurs that he thinks look so great on the mannequin aren't likely to flatter any human female bodies.
As such, I think if you're buying a gift for a female, and you want to play it safe, you should stay away from clothes. Taking her out to her favorite shop so she can choose something she likes is fine. So is getting precise instructions from her about what she'd like, clothes-wise. Otherwise, she could end up returning what you get her or having to exchange it, and that stuff is always a drag.
I can vividly remember how much I worked myself up in high school, trying to imagine what kind of super-cool gift my first boyfriend would give me. It'd be perfect, and symbolic of his awesomeness, and I'd remember it forever! And then the big exchange happened, on Christmas Eve. I opened up the nicely wrapped box he'd given me ... and found a shapeless pair of hippie patch-work pants with a draw-string waist. I did take most of my fashion cues from Janis Joplin, who was a hippie. But she wore bell-bottoms, not anything like the thing in tissue paper in front of me, which was essentially a pair of dressed-up sweatpants. Yuck.
I knew they'd been expensive. I knew he'd gotten them from my favorite shop in the mall. I really, really wanted to like them or, at least, to be able to act like I did. But I hated them. And because I was young and immature I didn't like him very much for a few days after that, either. I returned them.
Buying clothing for guys is, I think, generally easier. With men, sizing is pretty straight-forward. You ask him what length and width of pants he likes, what kind of collar he wears, what size sweater he gets, and you have all you need to know.
But what do you ladies think about all this? Do you think I'm missing the point? Are you happy to get clothing, because it's an intimate and thoughtful gift and you're happy to deal with returning it, if need be? Or do you agree that it's usually so dicey it's best to skip it? Would you prefer to get books, a thumb drive with a hand-picked selection of music, a season (or all three) of Arrested Development on DVD? Jewelry? Kitchenware? Or what about the gift of a cooking class, or a wine-tasting seminar?