I'm going to need new tired soon and I was wondering if 8.5/255 front and 9.5/285 rear would work with my TE-37's?

 

I have 245 and 285 with 8.5 & 9.5 rims, you could go 255 in front as I had them on my rear Rays which were 8.5 but you might want to be careful putting too much tire up front, they tend to go with everything on the road, any imperfection on the road and they will track it.