I travel quiet often and I can tell you that packing becomes painful when you have space restrictions. Or when you don't want to deal with checking in bags at the airport. This is why; with time I've gotten better at packing. Let me give you some tips to pack better:
Depending on how many days you are going away, plan the same number of outfits. Three or two days? Pick top and bottoms that look good together even when exchanged between each other.
Neutral Colors can make your trip so much more relaxing. Even if you happened to wear the wrong top with the wrong bottom (not how you've had it plan) if it's all neutral colors, you're almost guaranteed all combinations look good.
Wear only one statement item per day. You know I'm a big fan of minimalistic fashion. If you have some great shoes or new jacket you really want to wear on your trip. Give it the attention it deserves and wear basic clothing with it.