Is the rule exclusive to going out for ice cream?
Yes.
Are we playing yes / no questions only?
Does “going out for ice cream” refer to getting an individual serving from an ice cream shop (as opposed to buying ice-cream to take home, from any kind of store)?
Yes. Per the OP, I’ll let you know if the answer is “probably” or “I don’t know”.
Yes.
Does the answer have to do with when you go for ice cream? (I.e. only after work, and you don’t wear sneakers to work?)
Are sneakers shoes?
No.
Yes.
Ah …
Is the question why you have a rule?
Or why you don’t wear sneakers?
I’d say why I don’t wear sneakers. The rule exists to remind me not to wear sneakers when I go out for ice cream.
Okay, it’s not because you’re a loon, who just likes unnecessary rules.
Does it have to do with where you go for ice-cream? (does it apply whether you go to Baskin Robbins or The Mosquito?)
Yes. It only applies to certain ice cream shops.
Does it apply to a chain of ice cream shops? (Again, Baskin Robbins, as opposed to The Mosquito)
Do(es) the shop(s) sell primarily ice-cream or ice-cream type desserts? (As opposed to a Friendly’s, that serves other things)
No. Although it might possibly apply to a particular shop that is a member of a chain.**
In my experience, it’s been ice cream only shops, but it could apply to other shops as well.
Are your sneakers fabric?
Are your sneakers a non-woven material? (Leather, ‘manufactured leather’, some synthetic)
Does it matter?
I have several pairs of sneakers made of different materials or combinations of materials, but it’s not relevant to the puzzle.
Would the same rule apply if you were, for example, picking up dyr-cleaning from a store next to the one that serves ice-cream and weren’t buying ice-cream at all?
No.
Does it have to do with where you eat the ice cream that you get from these certain shops?
Does it have to do with what kind of ice cream you get from these certain shops?
Does it involve the type of shoes you wear when you don’t wear sneakers?