As my close friends know, I'm actually kind of a clothes whore. By that, I mean I love clothes, of course. I'm not into designer brands exclusively, just anything that look great or awesome or some hybrid of both.
So it won't shock them that I plot a lot of outfits for characters, even if I never end up describing them.
In House Calls, Sakura's got a few outfits I really like because visually they're pretty cool, but I never mention them.
Sakura's main, "work" outfit, would probably consist of something like a black tank top, white shorts, a black belt with hip pouch, and this sweater in red.
During the latest arc with the casino, she's supposed to be in a cocktail dress at least twice and one of those times you may picture her in this, because it is totally gorgeous. In Chapter 26, where it will be kinda sorta described, she's wearing something like this little black number with an additional inch or two to the skirt, although I stand in the reasoning that she could get away with a short skirt if only because she's so petite.
As for Kakashi, during the current arc concerning the casino and him having to wear, ya know, normal clothes go ahead and bask in the idea of him wearing this, sans tie. I don't know what it is, but I seriously have a thing for a man in a suit. Besides, it's basically the civvy equal of his usual get-up: vest, shirt, pants.