What does this mean?
How do I make it clear to the average person that I am an individual who "dresses well"? This doesn't mean edgy teens on tumblr
90% of it is wearing clothes that fit you correctly. A too-big suit will look ridiculous on you, regardless of how fashionable the cut/design is (unless the cut is meant to be oversized, which is a different matter).
Just start with well fitting, high quality, dress shirts and chinos and quality dress shoes. Tuck that shirt in and get a nice belt that matches the shoes. Tailor the shirt and trousers if you need to (which you almost always have to with RTW garments if you want them to fit as close to perfect as you can). Lose weight if you're fat and gain some weight if you're super skinny. Work on your posture. Work on your confidence. Get a classic mens haircut and keep your face clean shaven.
Also, I'm assuming you want the dressed up look based on the OP pic.
Who raised you?
idk why but from the way people talk about him I always imagined that he looked like pic related