Everyone understands that travelers have a limited wardrobe. We certainly understand that our fellow-travelers will be repeating outfits. For a block-long trip, pack one week's clothing. Darker clothes need less attention, look clean longer, and look fancier than the same thing in a bright or light color. A wool sweater is warmer, less bulky, and less heavy than a cotton one.
Knits travel very well.
Take only things that wash out easily. Adopt a color scheme. If your pants are black jeans and gray dockers, then you can wear many several different colors of shirts for lots of looks. Ideally, every item of clothing should go with every other item. If you tend toward pastels, green and purple might do it for you.