This is silly I know but I have self esteem issues!
Both of my DSs have no interest in clothes, to the point they wear the same things all the time. I would like to get them new stuff but I can't choose for them anymore (I don't know what's cool for an 18 year old...) but I feel guilty. Ds2 makes the odd comment and has come home a couple of times wearing his friends stuff but he will not go clothes shopping or even look online. Part of me feels terrible because they aren't 'trendy' like their friends, but also if they were that bothered they should do something about it.
Do you choose your 17-20 year old boys clothes? I was very independent so it's alien to me