- Unfortunate. "She's an... unfortunate-looking woman. That's the nicest way to put it, isn't it?" -David Sedaris's Mom, Dress Your Family in Corduroy and Denim. "That was an... unfortunate choice of words." Etc.
- Inappropriate: an excellent chastisement, particularly for business settings. You can write an inappropriate memo, say something inappropriate in a meeting, wear an inappropriate outfit, or conduct yourself inappropriately.
- Disappointing: "I'm disappointed in you." "That essay was disappointing." Their fake sadness and disappointment makes you feel guilty. As you should.
- What were you thinking? It's always insulting and annoying to ask someone a rhetorical question that has no good answer.
- Adequate. A great word for a book review. "So-and-so's latest effort is adequate, however..."
- "Well-written." My writing teacher uses this, and it is always followed with "but..." This is an example of a set-up neg, in which an ambiguous compliment paves the way for harsher criticism.
- Modest: "A modest little person, with much to be modest about."-Winston Churchill. Here, Churchill uses a word that is usually a compliment as an insult. The key here? Repetition.
It's so tired, simply calling someone bitchy or the son of a terrorist Jew! "The great thing about using feckless is that it lets you be extremely dismissive and mean without sounding mean; you just sound witty and classy," the late David Foster Wallace wrote, as Galleycat mentioned today. Which made us think about other succinct, erudite put-downs. (As with many things, we must look to the Brits on this one.) The secret? The adjective must be either rare, or mild. Like: "unfortunate":