I've lost a good bit of weight since I had purchased a majority of my clothes, so I see this as a nice opportunity to restock and switch up my closet. I'm 17 and my current closet consists of a rather dull formula. Tshirt + Poor fitting jeans = Today's wear of choice.

This sucks and I want to change it. I can dig Tshirts, as long as they have a unique look/graphic to them or if they're just a solid color. Not too sure where to find some nice shirts though. Besides Ts, anything else that I can sort of mix and match would be nice. I could definitely use some polos and button up shirts in the mix. I'm not going for any real trend or style.. as long as it looks decent and is comfortable, I'll give it a shot. Recommendations?

Now... this is where it gets tricky. Trying to find some nice jeans for myself is rough. I stand around 6'9'', 225lbs. Anyone got some advice here?

Well, if anyone could give me some pointers, it'd be appreciated. Breaking my malfitting monotony would rock.

Go shopping?

Just go to stores and pick out what you like/see if it fits

Eh, just looking for some recommendations for places. My interest in finding new clothes goes down with the more unknown options I have.

Find a good tailor, get tailored shirts = win.

Yeah, that is pretty P.I.M.P.

Standard question calls for a standard answer... the clothing you've asked advice about is pretty mundane and boring(IMO). It would probably just be best if you went and looked yourself, I mean, you're not looking for anything specific. T-shirts with a solid colour or graphics? Dude, you can find these anywhere... If I was familair with brands and such around Chicago I would have gave you a recommendation, but i'm not.

Go for Regular Fit Levis. anything goes with those

Boring and mundane questioner is trying to figure out how to appear less boring and mundane with said clothing or in general.

..I guess I probably didn't explain that very well in the OP.

Try staying away from graphic tees. Just go for solid colored ones or those that have simpler designs. Buy the colors that match your skin color.
Incorporate and experiment more with button-up shirts and polos.
Buy slim-fit jeans, I recommend Levis.
Lastly, the most important thing is that what you wear is not too loose or too tight. Your clothes should fit your body.

pffft