My daughter has long had a much better sense of style than I do, somewhat to my frustration. She will sometimes get dressed three or four times before she is ready for the day, which baffled me until I learned that her clothes have to match her self-perception for her to be comfortable in them; so each day, she has to recalibrate her outfits to match her mood. I understand about needing your exterior to match your interior - for me it is spaces that matter - but I had never applied the idea to clothing. For me, clothes are just something to keep you decent and warm and show appropriate amounts of respect for others; once I take into account the weather and my schedule for the day, I get dressed and quit thinking about it. Clothes very seldom reflect who I perceive myself to be. Which may be why I lack any real sense of style. (Something my daughter is working hard to change!)
One advantage to her approach to clothing is that I can easily read her mood just by looking at what she is wearing. Another is that she always looks great.