The very first step, if you are unskilled at putting outfits together, is to subscribe to or otherwise obtain several men’s clothing catalogs. This is the best way to study what clothes go together and what clothes look silly. Sign up for LL Bean, Land’s End, Eddie Bauer, J. Crew, and any other catalog that sells clothes you like.
Look at the outfits in the catalog and if you see a look you like, rip that page out. If you don’t want to purchase the clothing from that store, simply take the page to a store you do shop at and try to find something similar. It will help the store associates find you something you like if you have a picture of what you’re after.