The woman seems like she's trying to be nice and talkative, but I could't think of a scenario where coming up and saying "Aren't those the same uniform-like clothes as usual?" isn't kind of insulting in English, so I went the backhanded/unintentional insult route as in "Isn't that different from your usual uniform?"(Obviously not but this lady doesn't remember or care. She just wants to talk about the MC's clothes and hair, so she sets the tone with her opening question).
Now that I think of it, I could have just said "Are you always dressed like you're in this uniform?", and it would have been fine --it would just come off as curious -- but the way this lady starts telling her to fix her hair and wear new clothes comes off as kind of rude, so I thought the "different" route fit the tone of the "well-meaning but unintentionally insulting" person.
Darn, I figured out a more direct/literal translation that would work for me while going through all this:
"Aren't those the same uniform-like clothes you usually wear?" "The white shirt, navy shirt combo!"
That fits it well literally while being peppy but not insulting, but I still like it more when she just spends the entire conversation unintentionally dissing the MC. More fun and engaging, imo.