Traditional animal characters were often naked below the waist. Maybe that's one reason they were so appealing and funny. You wanted to laugh before they even did anything.
Modern designs are sometimes pantsless but they're designed in such a way as to de-emphasize the nudity.
For human characters the obvious way to go is clothes that are either too small or too big. I like the way Curly's jacket fits in this photo.
It works like this: the wife waits til her husband is busy with something then asks him a few questions that have an obvious "no" answer, questions like: "Are you saving this ball of lint?" "Do want this pencil stub?" "How 'bout his used Kleenex?" She gets a nice litany of automatic "no's" going then casually throws in the important item, in this case: "Do you want to save this ugly old Uncle Eddie jacket?" The first ten times my wife tried this I reacted with horror that she could even think of such a thing, but she persisted and one day when I was seriously distracted I found myself saying, "Huh... oh, yeah...sure...whatever..." and that was the last time I ever saw my jacket. Now I live in fear that my more-precious-than-rubies Wrinkle Jacket will suffer the same fate.
But I digress.
I like one-of-a-kind outfits myself.
Cartoonists should be fashion leaders, not fashion followers.
I like suit jackets (above) that flare out and stay flared.
What kind of dress shirt? One way to go is bulky one-size-fits-all shirts that always look ironed and new, like they just came out of the wrapper.
A certain kind of character should tuck in his shirt even though that's not the style now. In real life tucking it in requires constant adjustment and that's a great bit of business for a character with OCD.
Besides, tucked in shirts look great when they're pulled out (above) and allowed to hang loose. They retain their beautiful wrinkles at the shirt's bottom.
BTW, how do you like the crumpled forearm fabric and long cuffs?
Dress shirts come with all sorts of biases. This one is tight at the shoulders and loose everywhere else.
I wish I could have found a picture of a ballooning "parachute" backed tuck-in but, Alas!, it was not meant to be. Maybe next time.