Can i fit 285/75/16 tires on my 95 chevy 4wd if i add a leveling kit to it?

I almost think that you can fit those stock. But I don't think it would look great. I know a guy who had them on a 2000 model, and it was just too crowded. The leveling kit with those would really look good imo.

You could get 265/75R16 on them from the factory.

The 285/75R16 will fit just fine. Expect a slight amount of rubbing during a full-lock turn and the front suspension is compressed.

Forget about buying a leveling kit, just crank up the torsion bars. That is all the leveling kit does anyway is re-key the torsion bars, which is exactly the same thing as changing the adjustment bolt on the key. You can crank the bars for free. If I remember correctly it takes an 18mm socket; I would have to look under my truck to verify the actual size of the bolt heads.