Having just taken a look at some of the styles from New York's Fashion Week, I find myself asking the same question, not because any designers screwed up (that seems impossible on runway shows), but because I'm genuinely wondering what thought processes were at work.
My best guesses:
(Academy of Art University): "Hmm....let's take an outfit that fat ladies wear -- a baggy jacket, a loose-fitting untucked shirt, culottes, and a scarf to hide the double chin -- and put it on a skinny guy. Yeah, I bet that's never been done before!"
(Anya Caliendo): "What the public needs needs is a wedding veil for those brides who want to send the message that they're so horny they can't wait for their wedding night."
(Anya Caliendo): "We'll start a whole new trend: Triceratops Chic."
(Argentine Designers): "Let's see....if the Tinman from the Wizard of Oz tried to check his wife's oil when she wasn't in the mood, what would she have looked like afterward?"
(Betsey Johnson): "Hmm...let's dress up a model in hospital whites, to make her look like an escapee. We'll put a wig on her so she looks like that vacuuming woman in Something About Mary. We'll wrap her wrists and hands in gauze, like a boxer. We'll apply lipstick so garish her mouth will look like a bird's beak. We'll hang a small license plate around her neck. And we'll have her stride extra jauntily down the runway singing to herself. No one will think she has anything in that box but a severed human head. Yeah -- that's crazy!"
(Czar by Cesar Galindo) "Let's make a dress that a woman can't possibly walk in. All she'll be able to do is stand on a pedestal while people admire our creation."
(David Tlale) "Hmm....let's make something that's part dress, part negligee, and part veil, but make it sheer only around the breasts, so that no man can see it without thinking that he is basically being propositioned. We'll call it the So How Do You Like My Tits look."
(Elle Fashion): "First, let's create a top made out of sheepskin with sleeves about a foot too long. Then let's dye it to look as if some ink got spilled on it by accident. Then we'll add a sash that wraps around crookedly and doesn't quite match, or meet up in front. Then we'll gather up all the wool fabric clippings that have been left on the cutting room floor and stitch them together in a dress with uneven pleats and extra flaps sewn on. Then we'll combine that with samurai leggings and eskimo boots. We'll call it Expensive Homeless Chic."
(Falguni and Shane Peacock): "Let's put together a complicated design with two large dark spots on either side of the nipples with what looks like a large nose between them and some fat lips right below that. But the large nose will turn out to also be a torso itself with two nipples that could also be eyes. Then we'll put a dark triangle where her crotch is to add some allure. We'll call this the Fish Scales Rorschach Test look."
(Falguni and Shane Peacock, again): "This is the ultimate female assassin's outfit. At first glance it looks as if we're trying to create a Polio Chic look with those leg braces. But then the target's eyes will be drawn to the sight of her breasts, so she can quickly pull the knife out of her left "brace," which is actually a sheath, and run her target through. We're going to call this the Mata Hari."
(Fashion Shenzhen): "Let's find a model who looks as if she's been hypnotized and put her in a sheer dress with both her breasts and crotch line visible. We'll call it Sex Zombie."
(Female readers: just so you know, sheer tops are definitely in this year.)
(Jill Stuart): "Let's come up with a creation which is not appropriate for a single situation. It won't quite be a bathing suit, but won't cover up enough so that you can actually go anywhere in it either. We'll make it out of fine linen, too nice to wear for workouts. And the undies look will render it inappropriate for any sort of social occasion. This will stymie everybody!"