1. Hogwashers. When I came across this term in a David Sedaris essay, I needed Mr. SZ (who comes from a part of the country where people wear them) to tell me it meant overalls. Months later, Mr. SZ made me laugh by gesturing to a toddler in a coffee shop and saying, "That baby is wearing hogwashers." (Trust me, it was hilarious.) Hogwashers are even funnier when they're made by Dickies. Speaking of...
2. Dickeys. No explanation necessary. The item of clothing itself makes me chuckle, too.
3. Highwaters. Subject of the timeless elementary-school chant, "Highwaters, highwaters, can't be beat/24 inches above the feet." See also: floods (and the couplet "The flood is over and the grass is dry/Why do you wear you pants so high?").
4. Dungarees. That's what we called jeans when I was a kid. I am quite old.
5. Rubbers. I am old, yes, but I have the sensibilities of a sixth grader.