I'm a huge proponent of dressing in things you enjoy and ignoring any rules.
Growing up, I was deeply unfashionable. I was bullied for this at school. In my 20s, I was bullied at work for my clothes by a coworker. In my 30s, when I worked in marketing, and was surrounded by probably the most stylish cohort of colleagues I ever had, and I was frequently complimented on my sense of style. It was really weird. When I wore something unusual they thought it was a 'statement' and 'on trend' instead of being 'weird' and 'unfashionable'.
I could afford to buy new clothes that I wanted to wear. That's it. That's the main difference.
Style isn't doing whatever they tell you to in the magazines (I have never done that); it's wearing what you enjoy wearing and being able to afford clean, well-made versions of it.
Like, yes, you *can* thrift the odd good outfit, but it's a lot harder, and you're almost always making compromises. The people I knew who wore stylish alternative stuff as a teen and young adult were all spending £££ I preferred to spend on not being in debt. I occasionally see Tumblr posts saying the opposite, but in my experience, for most people, it's just not true. The people who looked cooler than me at Wendyhouse were buying New Rocks on credit cards. Even on eBay, that shit isn't cheap.
This is not to say that poor people can't be stylish. Rather: fuck anyone who bullies you about your style. Because they're not really bullying you about your style; they're judging you about perceived economic status. Your style is you and it's glorious. The people worth knowing will see you and your style in what you *can* afford.
Being 'fashionable' is keeping up with the Joneses. Being stylish is being yourself.
You can try to disguise or alter your shape if you want - if it's about achieving something that makes *you* comfortable. But it won't make you more or less like a man or a woman or neither or whatever gender situation you are trying to express. From an agender perspective it's very hard for me to understand how people see one piece of cloth as 'feminine' and another as 'masculine'. Or body shapes, for that matter. That, too, is a part of you, not your clothes. Because someone of a different gender or none could wear your clothes and it would not change a thing about who they are.
Clothes can't make you a man, but they also can't take that away from you. Be the most YOU you can be, and the rest will shine through.