Bottom line, you choose what you are most comfortable with. Depending on your personality, some may want to go with the flow and not really standout, maybe go the more traditional route. Others may want to be bold and stand out from the crowd.
For me personally, it depends on my mood. I always say “lets see how the spirit moves me”. Sometimes I will like a look and replicate it or parts of it (hair, makeup, shoes, clothes or accessories). Most of the time I don’t want to look like everyone else. For me that is boring. But that is kind of hard when fashion designers are the ones designing the clothes we wear so to some extent we are forced to go with the fashion trends. This is why I recently took a sewing class at my keep it ghetto fabric store on the upper east side where my mom used to take us as children. Shout out to “Save-A-Thon Stores”. Now I can alter my clothing to fit my personal style and body or even make it from scratch. And of course match my hair and makeup..
So, it comes down to preference, personality and mood.