Possible Clues:

• Don, as apparel (2 words)
• Add, as weight (2 words)
• It's not for real
• Assume
• In retrospect, no sheepish type gets an affected accent
• Try for fit, as jeans (2 words)
• Worn down? Contrariwise!
• Sounds like instruction to address local joke
• Produce a play
• Don boycotting university, perhaps, wanting a rise