Gary: This isn’t a typical letter, but far be it from us to spurn a cry for help. We suspect you’ve already read our series on men’s fashion. (If you haven’t, check it out here. Bingo!)
Now, regarding your question about colors: The trick, dear reader, is not to think of it in terms of ‘matching,’ as you put it, but in terms of coordinating. Stick with neutral-toned slacks. Browns and blacks are the most popular, but grays and even blues appear in the wardrobe of many a well-dressed fellow. Once you’ve got a good, relatively neutral base, you’re pretty much home free when it comes to shirts. Any color works: white, blue, yellow, even lavender. Just avoid most patterns, and you won’t need to worry about matching – unless you’ve also got lavender pants, in which case, you’d might as well get the whole ensemble out of the way at once. Run with it, Gare; the world is your oyster, and you are its nacreous pearl.