First off, you NEED a turtleneck, preferably zip up. We all know much Cloud LOOOOVES his turtlenecks. Second, he's still a pretty stylish guy, so how about a suit jacket with a pocket square? Now for the most part, he's a pretty emo kid (according to Advent Children >.<) So I would keep his colors pretty muted. The pocket square is where you could have some fun. Think about playing with color/pattern there. An example would be a navy suit with a bright orange pocket square for contrast. Normal slacks are still cool, but add a nice belt (could you do a wolf head belt buckle?). I personally like a nice dark wash jean, Especially since I see Cloud as preferring the more casual style, but still classy. The only issue there is if they would let you in with jeans on. Lastly, Jewelry. Think about adding a nice necklace and/or some rings, that would totally bling him off the charts (sunglasses=sweet). Hope we helped!!!!
-Syd and Rhe (You don't have to take any of this seriously, but it would look freakin' sweet)^.^