Caveat: I'm currently in the process of losing a lot of weight and really looking forward to hitting target weight and then getting a new wardrobe of good fitti

Caveat: I'm currently in the process of losing a lot of weight and really looking forward to hitting target weight and then getting a new wardrobe of good fitting stuff. It should be an adventure, and you don't need to do anything that other people tell you, but do take advice. That said, I dress like a sack of potatoes right now, so take this with a pinch of salt: Lots of good advice here, and basically buying more expensive jeans and hoodies that fit you better is going to be a start. Dark/black jeans and a really good hoodie that fits you well is not a terrible idea. Pair it with great sneakers. Then, start to expand into other clothes if you want to. I'd also suggest taking a look at https://www.reddit.com/r/malefashionadvice https://www.reddit.com/r/malefashionadvice - particularly the advice linked in the sidebar starting with the "Step by step intro". They will suggest: really think about your style and realise dressing well != dressing formally and vice versa; wear stuff that fits properly; buy one really, really good foundational item (like a really good pair of jeans), and build from there; colo[u]r matters; learn what clashes and what doesn't; try things and see if you like it or not. To get to the next step from where you are, there is nothing wrong with sticking with hoodies and jeans, but you could consider chinos, semi-casual shirts, polo shirts, jumpers or sweatshirts. Try new things, figure out what you like and don't like.