I think in this case, Dianthus, it's the idea that "old lady" is so often used in a pejorative way -- to reference something we don't like. Whereas "that looks like something a northerner might wear," presumably includes no pejorative intent. Er....I hope.
But ...Peri...honestly...I don't know. The thing is....there IS a style that can be associated with certain older women (i.e. the perms of their youth, the SAS shoes, the elastic waisted pants). Just as there are styles that we typically associate with teens or other age groups. Should we ignore that reality in our discussion and analysis of fashion?
In fact, perhaps when we say to a young or middle-aged member of the forum, "That looks a bit 'old lady' to me," we are not insulting older women so much as we are suggesting that the item or outfit in question seems age inappropriate for the forum member?
Is it also not okay to say (as we also often do...and in slightly pejorative way), "That looks like something a teenager would wear," or "That looks too "junior-like."
In fact, that may be exactly what the questioner wants to know! Does this look like something a 14 (or 94 year old) might wear. Because if it does, I am not giving the messages I want about myself. Clothes telegraph age just as surely as they do social class, profession, lifestyle, interests. And most of us (I think) want to suggest that we are stylish members of our actual age group rather than another age group .
I understand that age discrimination is not a good thing. And perhaps, by referring to the clothing in question in that way, we might be reinforcing stereotypes.
Granted, also, that various forum members have extremely different views of what is age appropriate.
I'm feeling a bit muddled about it, to tell the truth. I don't want to hurt anybody or reinforce stereotypes. But at the same time, I want to be honest to my own perceptions. And sometimes, when I look at an article of clothing or an outfit, I really DO think, "old lady."
Would I wear a pair of elastic waist pants even though I associate those with older women (primarily)? Of course -- and I have done so! Would I wear a hoodie or a graphic tee even though those looks are associated with teens? Yes again. But these are the kinds of items we need to examine with greater care to incorporate into a mid-years adult style. And being aware of their ordinary associations is helpful in that task. Or...at least...it's helpful to me.