Tires after the lift

I'm putting a 2.5" lift on my 09 Tacoma with the AAL in the rear. The tires on there now are 265s and I'll want to put something bigger on there. Will I need to do anything else to fit the larger tires, like 285s?

 

I have 285's with a 3" lift and had to do minor trimming to the front plastic on the well. I cut off those weird cone things that hand down in the front on the well. It was easy and took maybe ten minutes. It would have been less of a deal except I stabbed myself with the exacto knife....

 

I changed my 265/70/16 for 265/75/16, doesn't seem like much but looks better and didn't have to cut anything or remove anything. You might be able to get a set of 255/85/16 under there.