You can, I mean I can on new playthroughs. Maybe you need your character to have more confidence, or at least start with Sammy going out less dressed at night, or at the beach (that worked all the times for me)
Eventually Sammy will even walk around in her home clothes, or naked. However so far if she goes out bare (no bottoms no panties or no top no bra; the suits don't work either) she won't be able to do anything and the only location option will be "search for clothes"
Maybe tho my Sammy needs more exhibitionist training for that