Kelsey,
I have the same problem with pump wear! There just isn't much out there and what is out there is for kids! I talked to a local designer about making some pump friendly gear designed for women. She and I worked on it, but I never followed through on the designs. So for now: cleavage works for black tie, thigh high for skirts, the rest of the time it's on my hip.
I have a system of slipping it under my pillow at night and I end up with it wrapped around me several times a night. Yes the back light is my watch too!
I'm an avid runner, hiker and snowshoe junky! Let me tell you the pump hates extremes! If it's too cold it chokes, too hot it chokes! Snowshoeing I put it in my coat and I sweated so hard that it died. So now when the temperature is in question and I'm headed out the door for several hours, or the whole day, back to injections! Yes, major bummer, but at the same time the pump simplifies many things and is worth keeping.
Maybe we need to put our heads together and form a women's pump lingerie line!
Sorry Kelsey - no advice on the whole skirt thing...
C'mon Scott! No ideas?!