both tires have their place, both are functional, but unfortunately for the op he is miss-informed on some things/did not take them into account... for one like ripcord said the difference in availability of tires between a 255 and a 285... there are probably 4-5x as many 285s available as there are 255. also again as ripcord said drive skill has way more the play in this than the size of the tire, so do other things like lockers and the type of tire... also weight has a big factor in this as well, not all of our rigs weight the same, mine for one will easily tip the scales at over 5000lbs when i go out wheeling... if i where to be running 255s and i got into some thing other than hard packed rock and dirt id be fighting hard not to get stuck and sink down.
if you look at rally cars yeah they have skinny little pizza cutter tires for snow and ice stages, and wide tires for tarmac stages, and something in the middle for dirt stages... but then again you are talking about pro drivers and cars that are all pretty much set up in the same "basic" form... at that point its not so much the tire as the luck of the draw, and more importantly driver and co driver skill. and again they weigh next to nothing maybe 2800 lbs
i have wheeled every where from the beach to the rubicon, in all sorts of weather, from hot hot sun to cold and feet of snow. in my experience with multiple different vehicle, i have found that a wider tire does just fine, and in most cases in superior to a narrower tire. but i have never found a situation where a skinnier tire was hands down superior to wider tires.
but yeah be-careful about coming here and telling everyone that they are crazy and just ignorant of info and are all about looks. my father is of the same mindset, he constatly trashed me for wasting my money on such "wide" (lol yeah 285s are so wide), and then getting horible gas mpg with them... yet i look at all of his old pics from when he was into 4x4s and he had wide tires back then too -old ground hawgs like a 1500 series tire yeah... sure thats a little over kill especially on a old willys pickup but they did just fine and got him into so places i was amazed to see. last summer i took my father with me on a week long wheeling trip down in to lassen national forest in northern california, and he was amazed and how well i did with my 4runner and what i could do with it. -i was running my old 285 bighorns, that where at best at like 25% tread left and they went every where my buddies fj40 on 33-9.5s went and then some -and i was not lifted either at that time.
bottom line, i cant see a time or place where a 285 would suffer compaired to a 255 tire