@Kwaaked, thank you for your contribution....
I had hoped for serious suggestions to make the contests useful and accessible for everyone here.
It was somewhat serious if it helps. I find I am in an ugly clothing style at the moment.
Doing a monthly contest, or bi-monthly you've got all kinds of things to pull from.
Jan -Feb: Date night for Valentine's day
March-April- Easter (4-21 this year)
May-June - Garden party, since a lot of weddings will be happening.
July-August- Preparing for winter with a Coat, looking forward to fall or a summer blowout with the final garment of the season.
Sept-Oct: Halloween...could do costume, orange, purple and/or black ensembles, a Pearlies contest incorporating some form of bling (and really, I kind of love them), Guy Fawkes day outfit for the bonfire (aka: outerwear)
Nov-Dec- Holiday dress, Christmas sewing, New Years Eve outfit
General ideas not specified to a month or time:
pick a celebrity/royal and create an outfit for some type of soiree
favorite shirt contest with an explanation of why this is your fave style as part of it
fabric specific contest and choosing one outside the norm for most people (be it natural, shiny, knit)
fancy pajama/loungewear
color you normally don't wear
modernizing historical component/dress
lingerie/slip
Day to night challenge
Match an accessory you love and have nothing to wear with it.
Some obviously can be changed to fit, like Pearly can be an embellishment challenge or some such.