Murph, congrats on your new shirt, belt and bottoms! A red belt is most useful, you'll see. There are tons of other color combinations to be made with it too.
To answer you question: it really depends because noramally, my small wallet forces me to buy piece by piece (the ones on sale preferably) in hope of finding unity afterwards. This method also leads me to many returns, and some mistakes. Sometimes, in a store I know and trust, I will buy 1,2,3 pieces that work together. This represents a splurge for my teacher's salary, these items usually not on sale, but it is a much durable, useful purchase: sleeves'length will match, hems will fall right where they should, fabrics will work one with another for minimal creasing, bulking, and then I can play around for shoes and scarves. It's like buying a look instead of just one piece. Later, when I am in a rush of just not in a mood for thinking up an outfit, I simply revert to the original things bought together and go from there.