You dress well, and I appreciate your effort. It must be tough, considering how little cultural consensus there is on how to dress. Being older and from the northeast, I had an advantage growing up. I rarely claim "the good ole days" argument, but we definitely knew how to dress for an occasion.
For school and work, there were uniforms or dress codes. For church, we wore our "Sunday Best." For weddings (arguably the biggest of occasions) we wore several outfits; one for church, one for day, and one for night - the most formal and fancy outfits. For funerals we wore black. Men wore suits and pants. Women wore dresses. Kids wore shorts past our fingertips in length. For winter we bundled up. For gym class we wore sneakers. For sleep we wore pajamas. No mixing.
Some decided this was too confining, boring, stuffy, or costly. Not me. Coming from a humble background, having different clothing for different occasions meant our life was full of variety and not a monotonous stream of casual days in jeans. Because we were practical, I never found myself in high heels walking through a muddy baseball field or at a lake wearing a dress unprepared to swim. My clothes never made a statement as much as gave me opportunities to show different aspects of myself and positively engage in my community.
I cheer you on as you buck current trends of skimpy, elite, droopy, androgynous, effortless, and misfit clothing. Be practical, appropriate, and let your personality shine.