I'm 5'9" 220lbs and have glasses. Nothing tight fitting and nothing too expensive please.
Most Helpful Girl
First you need to find your own style, what you like and how you would like to look. There are a lot of trends and styles nowadays, and the only way to know what to buy and how to wear it is having a look in mind.
No matter how tall or heavy you are, the important thing is clothes fit you, not too tight, not too loose, just right.
For school is better if you wear casual clothes. For bottoms: jeans, casual trousers, cargo pants, depends on the style you are looking for, but no skinny pants either way and try dark colors as you are a bit heavy.
For up: decide on the shirts, it can be t-shirts with or without a collar, long-sleeves, short-sleeves, solid colors, prints, plaid or strips. You need a good jacket for autumn.
A good pair of casual shoes, not flashy, something you can wear a lot.
You could try the khaki pants, white tshirt, plaid button down shirt and jacket, casual shoes combo.
Go to a store and try as much combinations as you can and buy what you feel works together, ask for help, girls love helping guys choose their clothes ;)