I've been doing "it" this way for years and there's no real science to it. I simply place clothing on my bed and play match-maker with an ensemble. I usually start with one article of clothing that I def want to wear and I style the outfit around that. In this case it was the gray sweater vest. I wanted to dress up the look so I passed on wearing jeans and opted for navy trousers. A fitted blazer, Gucci loafers and a silk pocket square completed the look. Because I was wearing grays and blues, this was an "easy" outfit to style. Matching up colors, prints and patterns elevate the challenge. We'll talk about that some other time. For now, the take away is to work around a single piece of clothing and build from there. Oh and lay things out. Standing in your closet thumbing through hangers and hangers (and they better be wooden btw!) can overwhelm.
[my look: blazer-austin reed; vest-thom browne brooks brothers; shirt-7camicie; pocket square-century 21.]