Best: Red looks so good on you, that you're fine with that.

Worst: Red looks so good on you because you happen to be covered with an incurable plague of p***y red boils! They are incredibly painful, and the flannel shirt (while exactly the same hue) irritates your boils to the point where they start dripping all over the place. Everybody in your town is swept out to sea in a gian tidal wave of boil excretions.

Best: You were on a landing party from the Enterprise and Dr. McCoy is with you and he cures you of your nasty boils. And since the red shirt became disgusting with all the pus, he gives you another shirt to wear.

It's another reversible-ugly-skin-tone-clashing-plaid-on-one-side-red-on-other-side shirt and you're right back where you started.

Best: You paint it blue and the blue paint has no unfortunate side effects.

Worst: You look HORRIBLE in blue.

Best: your shirt magically turns pink

Worst: When your shirt was magically turned pink, it also became about 6 sizes too small and you can't breathe and you can't get it off!

Best: You miraculously find a giant seam ripper and tear the shirt off of you.

Worst: People aren't allowed to go walking around the Starship Enterprise without their shirts, so you are beamed down to the first planet they pass.

Best: It's a planet inhabited by lovable teddy bear things(or are they ewoks?) who make you their supreme ruler.

Worst: the Ewoks decide that you look like a god who would just LOVE to torture his people by making them eat him, nasty as he tastes.

Best: These Ewoks are really vegetarians so eating humans (meaning you) would be against their dietary code.

Worst: The Ewoks are not the only inhabitants of the planet and unfortunately, the Ewoks are lower on the food chain than the other inhabitants. After the Ewoks are gone, the other inhabitants take you prisoner.

Best: The other inhabitants are not so bad after all and treat you well as a prisoner and then release you.