There's a relatively small window of just a few years when being "cool" is considered to be important. Before 5th grade most kids aren't too concerned about it, because they all pretty much watch the same cartoons anyway and can have common interests in just running around and playing together. Around 5th or 6th grade, social pressure becomes very intense to conform. You're not supposed to like the wrong music, wear the wrong clothes, watch the wrong tv shows, etc. or you'll be ostracized and maybe even beaten up or worse. This is wrong and evil but it happens. If I had kids I'd try to buy them brand name clothes from 5th grade to 8th grade, when the competition is very intense.
I had some girls in sixth grade come up to me and ask me where I bought my clothes, and I said "Wal-mart, like most people", and they sneered and laughed the most horrible laugh and treated me like a piece of dog [censored] after that. They said they got their clothes at Palais Royal. That was the place where cool girls got their clothes back then (yes, very similar looking clothes to what you could get at Wal-mart, but they cost 5x as much because they had the all-important brand names on them).
Even my shoes were made fun of, because they weren't the pump-style sneakers that were popular then, and came from Payless. When I did get some pump shoes, I was treated slightly better and got some compliments on them, although most of my wardrobe wasn't up to par because I just didn't have an eye for that sort of thing, as to what was supposed to be popular.
Those things are very shallow and make no sense, but if it keeps someone from being targeted as different, then for goodness sake buy them.