Last year was the first year that difficult child cared about what his clothes looked like and what type/style they were- he was 13, close to 14yo. We live on a budget and I just was not going to spend more than $50 on a pair of tennis shoes and could not afford to buy him a bunch of new clothes just because he decided all of a sudden that he HAD to have a certain style. Plus, I think he was at an age where no matter what it was, he wouldn't like it just simply because his mother bought it. Ok, typical teen stuff. My mother got him a gift card for Christmas and I had a gift card that I "shared" with difficult child as part of his b-day. I told him I would put $50 toward the $60 pair of tennis shoes he wanted and he could pay the rest and use his share of my gift card to buy those shirts he wanted (but didn't need). I plan on doing something similar when he's released. He will have missed the holidays but I want to make up for that a little and he will definitely need a whole new wardrobe, however money is very tight. I was thinking that I give him a gift card, tell him how much I can/will put toward his clothes (outside of the gift card), so if he wants to spend more on clothes and shoes, it can come off his gift card or small amount of money Department of Juvenile Justice gives him upon his release. Does that sound too strict or reasonable? Oh- he will be 15yo about the time he's released. I will give him credit- when we did this last year it meant that he was actually shopping after the holidays so many sales were going on. He did a great job budgeting his money and got a WHOLE lot with only $100. That included a nice jacket that he did need and he bought it big so I'm hoping that it will fit when he's released and gget him thru the rest of this winter.