I'm going to have to do a color version of that outfit, because I think it might actually be okay (maybe not great) in color? I'm imagining the dark grey as red. This is mostly because that was a color used in the shoes where I used to bowl.
I originally just planned for Lucy to have an unusual look for the date, but as mentioned in the previous commentary, my brain went on a wild ride when trying to decide what Diane should wear, and the whole "will have to be paired with rental shoes" thing.
As for why Diane and Lucy don't own their own shoes, I don't think that's a mystery that has to be explained.
I'm gonna do it anyway, of course, but just quickly down here:
They didn't want to carry an extra pair of shoes around on dates, or wear them for the entirety of their dates, and they've yet to realize the someday-obvious-in-retrospect truth that they're not trying to impress guys anymore, and would probably save in the long term if they got their own bowling shoes.