I do this as well--so much easier. I got some e-bags for packing, and just have a basic pack in my bag at all times of toiletries, then one for underthings, pajamas, workout outfit, and then a clothes bag with a pair of black ankle-length stretchy pants, a couple grey tops depending on weather, and a basic black or grey ponte dress. Then i throw in (or wear) a pair of jeans, a jacket with a pattern (packs better), Tom's sneakers, and a waterproof black bootie in winter or basic black pump in summer. then throw in something colorful to switch up based on weather. In the winter, I generally don't take a coat unless I really have to. I just layer up a long sweater and a heavy wrap--so much easier to deal with.