I once had a French teacher in high school who--legend has it--purchased about a hundred pairs of the same shoe in the same size after deciding it was the best pair of shoes he had ever worn, and calculating the wear rate combined with his life expectancy. For him, my guess is that picking out what pair of shoes he wanted to wear each day was not an issue, but for everything else, maybe he could have benefited from a service called Closet Assistant, which as the name suggests is a system to help you pick out what clothes to wear based on what you've got sitting in your closet.
Similar to some of the bookshelf sharing services out there (Shelfari, Delicious Library, et al), Closet Assistant requires the user to manually input their inventory of clothing. Users can simply upload a picture, or go the whole nine yards by adding names, descriptions (complete with category and subcategory), price paid, and purchase date. Once added to their virtual closet, these items can be combined with others to make an outfit. You can then share these outfits with others Closet Assistant users (on a MySpace-like profile page), or schedule what you want to wear, and when you want to wear it until the end of time using the calendaring tool. Assumingly, users who set up their outfits for each day can do away with the annoyance of having to decide on what to cover up with each morning.
Is this useful? From an insurance standpoint I suppose it is (each user profile shows an approximate total wardrobe value), but what's interesting here is the social angle. How easily this can translate into a clothes swap or auction service, and integrate with other existing social networking sites is the next step. I'm just waiting for the inevitable Facebook app.