I totally agree on workout clothes with pockets getting priority wearing time...my workout shorts without them are pretty much always just "going to sleep" clothes now. Need that iPod!
I think out of all my shorts, pants, and skirts I only have 1 pair with a tiny pocket that would hold a key. (That's out of more than 20 pairs). I also only have 1 tank or short sleeve shirt with a pocket. Sometimes I miss the colder weather because all my jackets have nice pockets. My 1 jacket has inside pockets so I never fear losing things. When I'm out biking I like to have my phone at least. Maybe I should buy another top with a pocket so I don't have to only wear the one I wore above if I need a pocket. The thing is I'm cheap and the tank tops that I own without pockets cost me about $5 and ones with pockets sell for $30 or more. On long runs sometimes I wear my waistband pouch thing that can hold gummies and my phone and keys but I also hate wearing that.