In order to both make an initial "look" at a character more of holistic experience and more reflective of what a typical person would observe when looking at another person, I think it would be great to revise the tailoring system to reflect the changes made to the tattoo system a couple years ago.
Essentially, when implemented, new clothing would be required to have a @short_worn description in addition to a @worn description. When doing "look Character" you would see the clothing @short_worn descriptions and then when you want to get a look at the number of pockets on someone's pants, the color of the stitching along a skirt's lower hem, or just how someone's shirt magnificently contours over their love handles, you could `look pants on Character` or `look skirt on Character` to look at that article of clothing and how it sits on the wearer in excruciating detail.
I know this is logistically a nightmare and that there'll be thousands of pieces of clothing that wouldn't have this @message at first but the sooner this is implemented, the sooner that new clothing with a @short_worn message would become commonplace. In addition, I bet there's some people (including myself) who would be happy to help revise existing articles of clothing.