Peter Kaplan, the legendary editor of The New York Observer, wore the same outfit to work almost every day for decades: blue oxford shirt, tie, khakis and the occasional blazer. For Kaplan, it’s his uniform. It looks good. It doesn’t take much thought. And to me it seems like absolute genius. I am not deliberately sloppy. I have a sense that some things look better than others. But when it comes to clothes, my brain can never seem to concentrate. Which is why the idea of a Kaplan-like uniform—a single outfit, bought in bulk, that looks good everyday—is so appealing. It takes the thought, but not the style, out of dressing for the office. Ethan Song, the ever-chic CEO of Frank and Oak, an online men’s clothing boutique garnering a ton of buzz these days, agrees that it’s a solid idea. “I’m the laziest dresser in the world,” Song says. But different jobs, lifestyles and personalities, dictate different uniforms. To sort out what works for you, we’ve created this flowchart. Follow its path and you’ll be effortlessly stylish in no time.