Worst -
I have two - one was in the 80's. We used to as a rule visit Walton On the Naze and go to a pub called The Walton Tudor Inn. This was a New Years Eve tradition in my family. It was run by Ron and John a gay couple. Since sadly departed. All my Uncles and Aunts would go and the only stipulation was everyone had to attend in fancy dress. It will hunt me to my days that my mother was obsessed with Falcons Crest. So come new years eve we arrived, Dad was a bumble bee, mum was a butterfly, my younger brother was covered in cardboard boxes wrapped in foil and had come as Metal Micky and me - I came as a bunch of grapes LOL. oh dear. I was a vision in green tights, green jumper and a skateboarding helmet with a sign on it saying "Product of Falcons Crest" and of course the grapes, smothered from crotch to neck in green balloons. I arrived looking like a bogey, squeaking with the occasional dull thud as one of my bum balloons failed.
2nd one - Went on holiday to Cornwall. There are several pictures of me wearing a flat cap, a FELA jacket, jeans, and sporting a walking stick and Bowling shoes. I was 14. And despite my best efforts - every so often these pictures still surface now and then. However its usually my brothers attempt to take the michael. And now after a Chritsmas prank where I had to dress up as father Christmas because he bought us all these stupid outfits, there are some quite frightening pictures of my 6 foot, slightly tubby brother, dressed as Mrs Christmas (my revenge for the following year). Including assets and pig tails. We were all supposed to laugh and fall about at my brilliant revenge joke. Instead we sat there as he twirled in stunned open mouthed silence. It was quite intimidating
Still there you go