Not every day, but yes, I have done this and still do it. I was fortunate in some ways to have a son because his peers (if not him) were less interested in being supremely fashionable at every moment. Not meaning to be sexist here, but having been a girl in middle school, I remember some pretty awful times when my clothes (and I) were judged harshly.
Girls can be brutal about this sort of thing. On the other hand, my son had extremely strong opinions about what he should wear and what sort of hair cut he needed. At one point, he badgered me about getting tips of his dark hair frosted blonde, and after a month or so I consented. "It looked terrible. Why did you let me do that?" he asked recently, after looking at an old picture of himself.
"So you'd leave me alone," I replied. The truth is, I find dressing myself so exhausting, I have barely any brain space to dress anyone else.
Meanwhile, my son also tried an earring at one point, due to the example of an older stepbrother at his father's house. My husband complained that he didn't like hearing his wife and son discussing earring choices. I can't really say I blame him, because I had hoped having a son would buy us tickets into a fashionista-free zone. No such luck.
On the other hand, I am still convinced a girl would have been worse--really much worse, based on my own experience. My middle-school peers had strict rules about where you were supposed to buy your clothes, and they were often far more expensive than I could afford.
In high school, I found ways around that by wearing jeans, and to be fair, my high school was a LOT cooler than my middle school by virtue of being a LOT more diverse. It gave me the basis for a different way of looking at things, and a window into the kind of Beat Generation community I created in The Beat on Ruby's Street.
Right now, though, I'm thinking about how we choose clothes for our kids. I learned to always bring my son with me to pick out whatever he needed, whether it was jeans, shorts, bathing suits or winter coats. If I didn't, I ended up bringing the clothes back because he refused to wear them. So unless you are part of a religious community where dress codes are prescribed, (and maybe then too?) I think it's a good idea to at least consult them about what they wear.
I'm not saying they have to have the final decision. If you feel uncomfortable with something your kid chooses, tell them. If they balk, ask them who pays for their clothes (and remind them it's you, if necessary.) If you and your spouse or ex-spouse don't agree, then you need to hash it out and ask your kid why he or she is making the choice to wear the outfit in question.
All in all, though, I think kids mostly figure out a middle-ground of dressing that isn't too extreme, but you need to give them some of your hard-earned wisdom and guidance (whether they're listening nor not).
Because it IS our job as parents to make sure we're involved in their decisions. Otherwise, you're likely to wind up with an eleven year old who wears earrings and dyes his hair.
Oops. Well. At least his hair was never purple.
For more on this topic, I found these posts: