By Zach M., July 2008
Wear them a bit too high. The bottom part of your butt cheeks should be visible, at least when you are walking or running, or if the wind blows up the shorts. Wearing loose shorts is useful here because they flutter in the wind, which makes the exposure look less intentional.
Once in a while, pull at the hem of your shorts away from your legs, as if you are checking that the shorts are well adjusted. This can be used to draw attention to your shorts and to portray yourself as being self-conscious about their shortness. When you are resting your arms on the sides of your body, you should pretend to absent-mindedly touch the hem of the shorts with the tips of you fingers. Gradually, you then grab the hem with your full hands, always pretending not to be aware of what you're doing, a bit like when a girl plays with her ponytail.
When standing somewhere, put your hands on your hips, and use your fingers to open up the sides of the shorts slightly. It won't look like you are doing it on purpose.
To draw people's attention to your short shorts, completely readjust the waist band of your shorts. This draws more attention because you're using your arms and your shorts get moved around a lot. Take the opportunity to leave the shorts a bit higher than they were.
Use the wind in your favor: when you feel the wind blowing your shorts completely up, act like you're not noticing for some time.
You might want to wear constrasting underwear if you want to emphasize how loose your shorts are.
Crouch down to tie your shoes, to open up the sides of the shorts at their maximum. When getting up, don't forget that this you have a good excuse to blatantly readjust your shorts.
Use large store windows as mirrors to look at yourself in shorts. You may also start adjusting your shorts openly, assuming there aren't people on the other side of the window, unless you do want to give a show. Outside of normal business hours, most places are closed, so you can check yourself out freely. Such windows are also an opportunity to check how open the sides of your shorts get when you are walking. You can also get an idea of how your bulge appears to others and adjust it if needed.