When Fidel Castro died last week, there was no question about what he'd be buried in. Over the last half century, Castro was one of the leading proponents of the Uniform Theory of Style, i.e., the idea that a man should pick a signature outfit and stick with it forever. In theory, this sends a variety of positive signals to the world. It says you're extremely sure of your choices and your identity. It says you have no time to devote to the mundane routines of day-to-day living. It makes you easy to spot in a crowd, or buy presents for. All good, and generally speaking, we think the Uniform Theory of Style is an acceptable, albeit fairly boring way to go, especially if, like Castro, you plan to live to 90.

Superman. An early adopter of the Uniform Theory of Style.

So if you ever start thinking about going this route, just remember, a uniform is like a tattoo. Once you commit, it's very hard and maybe even psychically impossible to change it. The sunk costs of a dozen cashmere mock turtlenecks and New Balance joggers were nothing to a billionaire like Steve Jobs, and yet once he committed to his unfortunate Dentist Casual look, he proved, for whatever reasons, incapable of an upgrade. The man who envisioned the future remained, on the level of personal aesthetics, stuck in 1988.

So how did Castro, who embraced the Uniform Theory of Style so literally he actually wore a uniform, fare on a relative basis? Better than Jobs. Better than Mr. Clean (too matchy-matchy), Superman (who gets points for his cape but loses them for synthetic fibers and a visible logo), and the Supreme Leader of Toolbag Nation (who tries to obscure his obesity behind a two-man suit-tent of super 100s wool).

And yet, still, not so good. For 50 years, Castro looked like he was wearing a sack of laundry. In our estimation, only Fred Flintstone, the Black Panthers, and the Patron Saint of the domain, Hugh Hefner, have truly pulled off the uniform look. It is a feat that's harder than it looks.