In my game it's mostly Cassandra Goth and Yuki Behr. Yuki is a stylist and I honestly thought the randomness of that outfit was an intentional joke. Her clothes change as she gets promoted but she always wears the snorkel mask to work and other outlandish accessories.
With Cassandra though- she is in the Journalist career but goes to work in the fast food part time job uniform. Her wife in the same household, a born in game sim, goes to work in the correct military uniform. Her two daughters just aged up to YA and got new jobs and went in uniforms that looked appropriate. Interestingly, after the daughters got their new jobs, Cassandra went to work in what I assumed to be the correct Journalist uniform for a day or two. It seemed like generating uniforms for them triggered the correction on hers or something. But after the next time they traveled and came back home she went back to the fast food costume.
I have a sim in the Detective Career that goes to work in a clown costume 😅 same costume for another sim in the Criminal career... 😂
