gmBaggy ones are an obvious no no, but the tailored self made look seem to be popular but I haven't heard many girls comment on them. Most guys don't venture there because it seems to be a tough look to pull. Thoughts?
Denim shorts are on of those articles that looks good ONLY on a person w/the correct body type/shape. You're not wrong- it is an extremely difficult look to pull off. From a practical standpoint, it's probably better to invest in a more versatile article of clothing s/a khaki shorts.