When it boils down to it, I think it's more important to be fit and healthy than fashionable. Allow me to elaborate, using two fictitious guys as our subjects: Guy #1 - is in very good shape, dressed in regular Levis and and a plain white T. Guy #2 - is 30 lbs overweight, dressed in MMM / Dior / whatever floats your boat. I think that 95% of people would say that Guy #1 looks "better", since no amount of $800 trousers are hiding the fact that you're fat. Consider any fashion ad in the history of clothing - it's always an image of a fit, healthy guy modelling the clothes. Obviously. Imagine all the ads in a magazine if the clothes were being modelled by guys with 40+ inch waists. No matter what the brand, it would look terrible. It would be distracting. Any designer who did that would probably be criticized in the press for picking on fat people. I don't think most clothes are even designed to be worn "fat". They're designed to be worn by someone with slimmer "ideal" proportions. Thankfully, this is not an either / or choice. You don't need to choose between fitness OR fashion. Hopefully you're working on getting in shape at the same time as you're picking up interesting pieces to create a unique wardrobe. I'm not hating on fat people, but I am hating on being fat. I've been there (40+ lbs overweight, down to 170 from 215) and no matter what, it's hard to feel good about the way you look when you're fat. I remember being in a fitting room looking at my gut, thinking that I needed to change my ways... and I did! But buying and wearing nice clothes has never been more fun now that I'm in shape. So, fashion or fitness?