how am i supposed to know what looks good and what doesn't? i can't even fathom how people know what looks good.
alright im going to start trying to help instead of belittling and putting you down like other people here are.
Haircut:

Glasses:

https://i.imgur.com/dAQgvni.pngreplace the button down shirts with some t-shirts, keep the flannel. you don't need 5 pairs of shoes, one or two pairs are enough. all black vans or nikes are good. at the least get tan chinos, darkwash slim fitting jeans, black slim fitting jeans.
get some more t shirts at least, with NO GRAPHIC SHIRTS WITH THE STUPID WITTY SAYINGS LIKE "I'm so next level" with a picture of a game controller. If you want to be taken seriously burn those if you have them. good t shirt colors are black, white, earth tones, but get anything that is versatile and goes with a lot of outfits. don't be the kid who wears nike everything
also learn to layer clothing if you live in colder areas. flannel + hoodie underneath is a good simple fit, bomber jacket over a hoodie, bomber jacket over a flannel, dark flannel with a hoodie over that and another flannel over that is good too but make sure the base flannel is a dark color or you might look weird.
smelling good is better than smelling like nothing, get some polo blue cologne or something.
http://imgur.com/a/X19q7 here are some more sporty outfits for warmer temperatures. ask me if you need any more tips.