Yes, a friend was running LT285s (on stock rims) on his 2000 Quad Cab 4WD 1500 for 4 years without any major issues. They looked a tad big for the wheel wells, but then again, they looked better than the stock sized tire.
A a 285 will work but idk about a 305 or a 33x12.50. The 285 is only 11 inches wide compared to 12 and 12.5. I have 33x12.50 on 15x8 with 3.25 back spacing and I about .75 of an inch from rubbing at full lock. And thats with 3 inch lift.
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