When I was 5 I wanted to be a chocolate chip cookie. I remember vividly driving up to a dumpster behind a big box store to find a single piece of cardboard big enough to make a me-sized cookie. Then I got all upset because everyone at school wanted to eat me 🤣

• Went to army surplus store, got various stuff, also got peace buttons and a headband, took all my hair down (long hair), and wore the military gear all unbuttoned and disordered. There wasn't really a plan for the costume beyond that, but people partway through the night decided I was Ron Kovic, which seemed like it fit even though I had no wheelchair. I had a photo from that night for a while with a friend who was going into the navy, who was dressed up as some kind of special forces man with a big hunting knife, with us standing together him looking like a psychopath and me smiling doing a peace sign. We were the before and the after.
• The day I cut off my long hair, I invested in a super-sharp suit, and went before work to get it all cut off and get a super-sharp short hair haircut instead. I showed up to work in full suit and tie, neatly shaved, looking like a completely different person. My coworkers kept getting startled because they would look over at my desk and see this suit guy sitting there for some reason instead of me.
• When I was in my mid 40s I dressed up as an old man. Powder in the hair, glasses, old man clothes, and moved around all slow and careful and looked over my glasses at things. People were alarmed a little bit by how effective and accurate it was lol... like "I don't want to see you this way, stop stop doing that."

Those three I all enjoyed quite a lot.

Not me, but my spouse. In 2008 as the economy was tanking, she went as a box of Franzia. Painted wardrobe box with 2 bladders of wine in there, she took days to paint the box like a real Franzia box. Thing must have weighed 20 pounds. Went to a parade and huge outdoor event and she was very popular. Those nozzles saw a lot of action, and were basically a public health danger 30 minutes into the night. The wine lasted hours and she ditched the box with some wine still in at some house party we passed.

I have a big bushy beard which somewhat limits my costume options if I'm going for any kind of accuracy unless I want to wear a mask

My two standby costumes that I dust off when I find myself with unexpected Halloween plans are

A lawn gnome. I dye my beard white, put on a blue ren faire sort of tunic, a wide belt, and a red pointy hat

And a Monty Python lumberjack. Red flannel shirt partially unbuttoned over a bra, suspenders, high heels, and a knit hat. I also have a big ol' double bit felling axe I may trot out if the occasion warrants it.

I suppose I can also lose the heels and bra and just be a regular lumberjack.

When I was in college I decided to go drag for Halloween. I got the gayest dude in our dorm to pick my outfit, wig, do my makeup, and make sure everything was perfect. Then a bunch of us went bar hopping and it was easily one of the best nights of my college life.

Plague doctor in 2020.

Ninja samurai, not quite a samurai but wearing more (cheap plastic or foam) armour than a regular ninja. 9 year old me had it so good. The sword almost lasted a whole 20 minutes of play

Not for halloween but for a friends birthday costume party when I was like 19: I strapped a cone of white paper to a head torch on my head, then sellotaped a piece of paper to my t shirt that said “I’m a fucking unicorn” and won the costume competition there lol. I didn’t know it was a costume party till last minute and improvised.

Zombie. At college I had a costume party coming up with few options. However I had a ripped sweatshirt and a bunch of plastic spiders and rubber snakes. A bunch more rips, some strategic dirt, and attaching the critters turned me into a passable zombie. I really liked the results.

Note: I wish I had the confidence to….. the winners at that party was a couple dressed in trash bags. Only trash bags

IRS agent, I had a clipboard and a plaid jacket. I looked the other way for an extra piece of candy. I came home with stuffed pillow case full sweets and a pencil, fuck those guys.

Did way more Halloween stuff in my 20's-30's, slowed down a bit in my 40's but still go out to events in October.

I was a Chilean miner in 2010, that one was fun since the mining accident in Chile was all over the news at the time and people immediately recognized the hardhat and whatnot.

Another year I had dressed up as a sort of sleepwalker complete with bathrobe, slippers, etc. But it turned out that was way too vague and everyone called me Hugh Hefner that night.

But most years I was a bit lazier and just turned myself into a zombie with makeup, fake blood, ripped clothes, that sort of thing.

“A bad night”

Handcuff on one wrist, dress shirt ripped, tie still on. Hair messed up, lipstick, blood, dirt, and no pants.

Went clubbing like that.

A vandal. A visibly hand-made empty egg carton, a baseball bat, a ski mask, and a candy sack. Felt pretty proud of myself with that one.

The Spanish Inquisition from that one Monty Python sketch. I was 15.

Not Halloween because that's not a thing here but for Karneval I had the coolest Spider-Man costume. At least it's the coolest in my memory. Anyway, imagine a beaming 7-year-old running around as Spider-Man for months at every opportunity with her blonde hair sticking out under the hood (which was really more like a Daredevil cap, probably so that kids don't asphyxiate themselves).Then I lost the hood. Still used the rest as a pyjama for as long as I fit in it.

Another time I was a witch disguised as a clown. I don't know why. It was really just a collection of weird, mismatched clothing articles and some clown make-up.

And for some reason, at one point I REALLY liked this guy:

Not Mickey but the Phantom Blot. REALLY wanted to be him for Karneval. So my mum took an old sheet, dyed it black and then I had to explain to everyone in my class, one after the other, that 'no not the phantom of the opera.....'

I once went as a TV. Basically just a huge painted box with a cutout with Saran Wrap over it as a screen and a pair of my dad’s suspenders to keep it on my shoulders. I have no idea how I collected candy in it, I suspect my parents had to actually do it for me.