This is difficult for a number of reasons. As I mentioned in a previous post, the big reason is that sizes are not standardized. A size 32 waisted pant can be a true size 32, or really a size 38. Also, people's sizes fluctuate, usually increasing.
The 2nd part of your question, simply defining what style of clothing to wear is even more difficult and probably impossible to automate. However, there are professionals you can hire which will solve the problem for you. It's not cheap, but if you're single and make a good programming salary it may be a better investment than the latest digital camera or gaming system.
The 2nd part of your question, simply defining what style of clothing to wear is even more difficult and probably impossible to automate. However, there are professionals you can hire which will solve the problem for you. It's not cheap, but if you're single and make a good programming salary it may be a better investment than the latest digital camera or gaming system.