The subject line might be misleading--I mean "worst" not in terms of design, but in terms of construction and practicality.
From 2006 through 2008, full-size candy masks were sold in many outlets around the country. Seems like a cool idea, but hell, you couldn't hold 'em against your face long, and once you did wear them and get them sweaty, you wouldn't want to eat them! And they're huge--take you a week to eat 'em, and by then mold spores or ants have gotten to 'em anyway. Yikes!
Just as bad as candy masks are sticker masks. Here are pics of some Jane and I found of this really bad idea for Halloween disguise:
No, they won't wrinkle, sag and look bad in ten minutes, or itch in five. Of course not. How could I think such a thing?
A precursor to those dumb paper sticker masks are starched cheesecloth masks. They've been around since at least the 1930s, and possibly earlier. My older brother and father remember wearing them, and how soggy your exhaled breath got them. Of course, by the end of trick-or-treating, you had a sort of melted look on your puss.
Here's an example in remarkable shape after many decades, proving it got little use:
Of course, during the Depression and until the Fifties, modern plastics were not available. Perhaps more durable in use were cardboard masks like these old Depression-era devils:
But the very worst mask idea is a kind you see, rarely, on adults--the permanent kind:
I suppose, if you want to become one with your "mask", to change your mundane life's role into one more like the one in your head, the one you wished been born into, it's the best mask. But talk about a mask that'll get distorted, wrinkled, and saggy! And if you find a different mask you want to become one with later, that's too bad.
These guys shoulda learned how to put on makeup.
Thanks to Bobby Beeman for some of the candy mask pics.
Image source for demon lollipop mask: Flickr account of RhiaP
Image source for face tattoos found here.
Image sources for Lollipop Masks are here and here.
Gauze mask images found on eBay.