Yep, same problem, except my Sims had already bought the shirts themselves before reaching that point in the aspiration (unlike the OP who had someone else in the family buy the shirts). As a result, I don't believe the OP's workaround of leaving for another family would work for me.
@ae2e2ad59c70318d I've also had a sim buy it before they reached that stage, that's when I first noticed the issue. The purchase of the shirt is actually tied to the household so if you move the sim out of the household that sim who already purchased the top will get the option in another household. However if you only have one sim in the household I expect you'd have to move a sim in first, and then go back out to manage households and temporarily move the existing sim to another household and then have them (re)buy the shirt. I just tested with a household that the sims had purchased the shirt before they reached that part and that did work for me. I wasn't sure which of the two sims had purchased the tops so I took turns moving them individually out to a different household and they both had the option to buy both shirts when they were in the different household (though of course that second household can't have already bought the shirts).
These were both my sims' options at the stand after they had been moved out to a different household even though one of them had purchased the shirt before they reached that stage. Both only had the option to wear the shirts when in their original household where the purchase had been made.
Best regards,
Jennifer
