The present perfect is useful to ask questions where there is a connection between the event in the past and the current state.
In this case you can understand that the first two questions are asking "Is your dress sense now, different to how it was in the past?" The connection to the present is clear.
But the last question introduces the phrase "In your 30s, 40s..." That places the question as a question about a particular time in the past. So the past tense is natural.
Compare with this dialogue:
Have you eaten recently?
When did you eat?
The first question is really "Are you hungry now", and the connection to the present makes "have you eaten" natural, even though the phrase "recently" refers to a past time. The second question is about the past. Tense is chosen appropriately.
Similarly "in later life" keeps the connection to the present. Whereas "in your 30s" makes it a question about the past.