For me it’s the shoes that matter most. “Clean” is the bare minimum for projecting a well-dressed image, even in a casual setting. In my circle I don’t see a lot of tailored outfits — people dress more for studio work that involves hours of rehearsals, lugging instruments from one location to another, building sets, writing screenplays, etc. This doesn’t imply that they don’t dress well, although one sees quite the gamut of outfits and attention to style. On the other hand, in a concert performance, for example, the manner of dress tends toward the formal. Concert dress is frequently more of a uniform than a statement of style. During the workday, though, my own personal aim tends toward “smart casual,” which typically involves a blazer or sport jacket with chinos or selvedge jeans and shoes. From my experience, the shoes are what get noticed first, then the blazer, then the shirt and pants. (It occurs to me that others who are reading this may have different experiences.) In any case, this is why I pay particular attention to the shoes — their cleanliness, for sure, but also how they help provide a foundation for the outfit. However, having read other perspectives on this question, I’m feeling inclined to adopt regular visits to a tailor as part of my routine. (Grateful for the perspective!)