Brash Jeff: I can Guess That Theme in two entries.
BOOT CAMP …
HAT TRICK … Things you can wear!
Bzzt!
THIMBLE RIG … Things you can wear!
Ahem. You already guessed that. Bzzzzt!
IRON MAIDEN … Things you can wear!
Bzzzzzzt!
Well, technically you could wear an IRON MAIDEN. It wouldn't be comfortable, but you could—
Bzzt bzzt bzzt!!!
I love getting bamboozled by a Monday theme. Hitting the revealer—MONOPOLY tokens—I slapped my forehead. I should have gotten it. At least, I should have stopped guessing "Things you can wear."
The BOOT, HAT, THIMBLE, IRON, DOG, aren't a complete set, but it'd be impossible to include all the kooky items they've used over the years. A penguin? T. rex? Don't even get me started on the Pokemon collector's set. I choose you, Pikachu!
What's most important is that the theme set screams MONOPOLY, and this does just that. I'd never heard of THIMBLE RIG, but the THIMBLE is one of the iconic tokens. (The one I always got stuck with. Seriously, a THIMBLE?)
Maybe I'd have used WHEELBARROW RACE in there instead, paired with IRON SUPPLEMENTS. My brother always got infuriated when we landed on the same spot, and I invoked the wheelbarrow carry rule. Your token goes onto mine, and then you have to pay rider's fees, doubling with each step.
What, you never played Calvinopoly?
Stellar gridwork, as I've come to expect from Christina. She did everything right—squeezing BOOT CAMP and HAT TRICK together for smart overall themer spacing, wisely alternating her long down slots (DADS TO BE not interacting much with COWBOYS), choosing great bonuses (SHARK OIL and NO CAN DO!), and all the while, minimizing her crossword glue.
Making a crossword isn't rocket science, yet forcing yourself to work with only common short words and names is something that few constructors adhere to. The great majority give in and say "good enough" way too quickly. Not Christina, always putting in the serious time and hard work required.
Exemplary Monday offering. I'll be pointing newbs to this one, and that's the highest Monday compliment I can give.