To go outside with a bot you need to speak with lady from clothing store about it (just keep coming to the store for a while and she will ask about your girlfriend). Bow tie isn't necessery in order to go outside, but a skirt is, I hope you can get it if you keep coming there, I know no particular way to find it, sorry. After going to clothing store for a while, if you buy a lot of clothes, you will get access to premium program where you could get any piece of clothing you want.
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I dont think premium program is linked to a day. I think it might be linked to amount you spend at her store, and maybe whether or not you come there with Jun. It happened around day 18 for me. Not sure what happened with the skirt for you, it could be a bug, or you're just very unlucky. I hope you can get it soon