No, I don't think it wouldn't look that bad. 285's would look better though.
That's the lift I have by the way. I'm very happy with it.

 

I put a 3 inch with 295/75 R16 and keep the stock rim and it looks great. good fit to

 

I have to agree with your point. I wear out my tires before changing them. Since you already have them, use them. A two inch kit or levelling kit would do well. After you wear out the 3 sets of tires, if you still have the ride then change stuff. Check with the local 4X4 shops. A lot of guys will trade their trucks and sell the wheels and tires so the dealer doesn't get them for free. Another thought is do you plan on larger tires and lifting it in the future. If so, plan the lift strategy so you don't buy stuff that will be tossed later.