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They would fit , but they would bulge out on the rim and be quite a bit taller than stock. Harley rims are 20x8" correct? I don't think it would look good. Maybe a 295/45/20 or 295/40/20 Just my .02
I purchased the 305-50-20s today I replaced the 285-50s that were preveously on the rear. The 285s gave the truck a great look more muscle I guess, I put the new 305s on and wow they look great bulged on the sides & yes taller makes the truck look even more muscular. The harley wheels are 20x9.