Heh, I think I have a pretty good idea which board it could be! I have to say I am kind of middle-of-the-road when it comes to the kids clothes. My kids are still young. I do pick their outfits and I do put them in things that match. If ds is getting ready to go out and grabs his red shoes I will say something like, "The red shoes don't match because there is no red in your shirt. Grab the brown shoes instead, OK?" He has never protested. I just view it as a way for him to learn how colors and patterns go together. If he ever actually expressed an opinion about what he wanted to wear, I would experiment with ways to allow him to choose while still attempting to match. When I buy his clothes, I do go out of my way to buy things with themes that reflect his interests--cars, construction, fire trucks, tractors, etc.
I would not make them wear something that was uncomfortable for the sake of looking cute. I rarely buy fashion shoes from children's clothes stores because 95% of them look uncomfortable and poorly made, especially for the price tag. I buy two or three basic pairs of shoes that will match everything, and I shy away from things like flip flops that could hurt their feet, or straps that could rub. I stick with comfy cottons for the prewalkers. One thing that bugs me is seeing a scrunched up newborn all decked out in embroidered denim jeans and a shirt and a cardigan or hoodie and a pair of stiff shoes and a hairbow.
mommy to ds 11/05, dd1 01/08, and dd2 01/10!