Bigger Tires or nah?

Hello, right now I'm running 265's with 3 inch lift in the front and 2 inch in the rear on my 06 Tacoma. I am running 265's and want to bump up to 285's soon. But I'm afraid I'll have to do a little trimming if I go with the 285's. The 265's don't look quite to small now but it seems to look like I can jump up a size. I also don't want my tires to look too big, but I really like the more aggressive look. If I do jump up to the 285's I will have to run wheel spacers to clear the UCA. What do you think I should do? Here are some pics.
Thanks.

 

I fight with this same thing every time I get new tires.
The 265s win everytime because of exactly what you said.
285s would be nice but......

 

Could defiantly use some more meat. Are there no 275 options?

 

Just run 265/75/16

 

Plan on cab mount chop, pinch weld flattening, and quite a bit of inner fender trimming to fit 285's.... those that say they can with minimal trimming dont flex their truck more than the curb at the mall going straight.

Now 255/85R16's on the other hand will fit with much less than 285/75R16's cus they are much skinnier (and look better IMO), yet are essentially the same diameter as the common 285's