Whether by combining related prints or pieces of the same hue, playing matchmaker takes a lot of confidence. This is a boldness in an exciting new form and it's certainly a risk - not so much for the effortlessly chic crowd as the avant-garde creative types.
The three model outfits I've created below are inspired by some outfits I saw walking the streets of Italy as well as my own brainstorming and ideas.
My rule of thumb is that when matching pieces, make sure to maintain one subtle difference. Perhaps ironic, but adhering to this principle ensures that your look's multidimensionality. As you'll see in my creations, each match uses slightly different hues or prints of different scales, injecting your look with more depth and personality.
Fashion cannot be for the faint of heart or there is no fun. Everyone needs excitement.