I guess the most unusual Halloween costume I ever wore was as the Mushroom of Honor at my closest friend’s Halloween wedding back in the late 80s. She was Queen Elizabeth I and her betrothed was Mr. X. (Amazingly, the union didn’t last!) There are pics somewhere, but I’m too lazy to dig them out.
The funnest costume I ever wore was Mae West. This pic was snapped just after a “find your cherry” pie-eating contest. I won.
Fun times. 
I’d carry a little pouch with a bottle of suntan lotion too.
Unfortunately, you’re right. I always seem to end up in places where it’s too damned cold to go out naked after August. 
Can I come up and see you sometime? 
I once saw a man dressed as a farmer with a sheep attached to his groin. Always wanted to replicate that one.
ROFL, prize for being the first!
Hey, MacLeod! Get offa my ewe! 
That is insane but would be wondrous to behold in the wild.
I mounted two styrofoam wig heads on my shoulders and went as a three headed man. They had strings attached that I could pull to make them nod individually.
An Australian on holiday in New Zealand is walking through the countryside when he spies a farmer shagging a ewe.
The Ozzie says “Y’know mate, where I come from we shear those!”
The Kiwi replies “Bloody hell! I’m not shearin’ this with anybody!”
That’s creative!
I once went as a poorly put together Medusa with a paltry number of snakes attached to my head…maybe with clothespins? I can’t remember but it was a memorable flop.
Dollar Store Medusa.
Or - in my era - Five and Ten Medusa.
Good one!
You just reminded me of this:
I once dressed as Malibu Barbie. That may not seem extreme, but if you knew me, you’d have been quite startled.
LOL - they don’t give a lick.
You’re not from Minnesota are you? 
Hey, walking on bare tip-toes and lying on a beach towel on the floor next to Ken was damned cold! Plus I shaved my legs and armpits, which I didn’t do at the time, so I was extra goose-bumpy in that bikini. Poor Ken wore only a stars-and-stripes Speedo.
Kink-y!
It was one of those “the lesbian-feminist confounds your expectations” evenings.