Nah. Unless he's just wearing a tee and sweatpants, he should just hire a stylist. Joe comes off like the type that equates dressing well with the clothes being expensive. If you can dress, you could look good with clothes from a thrift store.
Joe seems to be stuck in the 90s/early 2000's when oversized clothes were in. Maybe he does it because of the weight. He's said himself he can't dress. When Ish was saying Joe is wasteful, this is partly what I took from it. If you are going to mostly wear sweatpants and white tees, they don't need to be expensive. If you are going to buy expensive clothing, consider how the clothes look on you. Two people could be wearing the same fit and it looks extremely different just because of your build. If you find that you can't do it, add a stylist to your budget.
Basically, don't be the person wearing the Gucci outfit top to bottom. Yes, it's expensive, but it usually doesn't look good.