I don't think it really matters, all things being equal. Unless the location is more upscale. For instance, if we are spending part of our time at dinner or having a cocktail at a nice restaurant, etc. then dressing it up a bit is a nice touch. I know I always dress for the location. Sometimes, a nice black dress with a hint of cleavage is more appropriate that a resort-casual sun dress for instance. Just my two cents. Ultimately, though, I'm more interested in the man inside the clothes. - London