People often say "dress for the job that you want, not the job that you have." But what happens when one of the apparent perks of seniority is the freedom to wear much more casual clothes to the office?

I've worked in multiple offices where the day-in-day-out dress of my superiors was much more casual than I could get away with. I don't mind dressing more professionally for work, but I do wonder sometimes if there is such a thing as being too formally dressed compared to the person who you report to, especially if I get pulled into a meeting with people outside of our immediate office.

Does anyone else run into this issue? Do you try to harmonize somehow with the casually dressed superiors or just wear what you find comfortable/professional/appropriate?