Welcome to the ultimate collection of “What Were They Thinking?” moments in fashion history. Each outfit featured here tells a story of bold choices gone terribly wrong, from homemade prom dresses that look like craft projects gone rogue to celebrity fashion moments that their stylists probably wish they could forget. We’ve included exclusive interviews with fashion experts who break down exactly why these looks don’t work, and how they could have been saved. Plus, we’ve gathered hilarious social media reactions that turned these fashion faux pas into viral sensations overnight.
The Jeans Dress – The Jress.
We never thought we’d live to see the day when the jeans dress (otherwise known as the “Jress”) would reign supreme. Thankfully, that day hasn’t come yet. But this picture of an incredibly fashionable model posing perfectly in a jeans dress makes us wary. Like, this could definitely pass as a Vogue model or something. We just hope this won’t start a new wave of Jeans-dresses that’ll override whatever’s going on today in fashion.

Not to say that the model’s doing anything wrong – she’s just doing what she was paid to do. The problem lies with trendsetters of our generation. To them, we say: Please don’t usher us into the age of the Jress.
The Tactical Espionage Camo Look
Other than the two suction cups with strange valves coming right out of them where the model’s bra should be, this dress would definitely fit in a piece of desert camo reserved for super, top-secret agents and James-Bond-like spies. But those suction cups are quite the discrepancy, especially when you’re trying to camouflage yourself. Didn’t this lady learn anything in camouflaging 101? You’ve got to blend in with your environment.

Also, we haven’t touched on what’s going on with her feet. Are those shackles? Is that a bunch of scrambled tinfoil? Why does this lady have tinfoil furled across her feet?
We’re Just as Mortified as Her
We’re not even sure what is going on in this picture or why this fit is so horrendously terrible, but we do know that both we and the person wearing it feel terribly uncomfortable. Maybe that’s it, though; maybe it’s just the fact that the model is feeling incredibly uncomfortable in this suit which makes the whole fit look bad. On the other hand, something about just doesn’t seem right.

Which is strange given just how fashionable suits and formal dresses tend to be. They just tend to look good on most people, regardless of body shape and build. Not this time.
We’re Not Sure What’s Wrong With This Dress But It’s There
It’s hard to point the finger on the exact thing that makes this dress seem outlandish and bizarre, but it’s definitely there. We cannot be the only ones imagining it – something is just a tad bit off with this dress. This, by the way, is perfectly acceptable; there’s nothing inherently wrong with wearing something weird, but one should own up to the fact that he is wearing something weird.

Anyways, we’d be thoroughly spooked and perhaps even a bit weirded out were we to witness somebody casually strolling around in public wearing this dress. We wouldn’t know how to react.
Just Came Back From the Ocean Floor Look
Oh, damn. She’s got the Moss-11s – the rare piece of underwater apparel that doubles as both a dress and vintage streetwear. Okay, we’re just making things up. But could you imagine a world in which growing live plants on your outfits was socially acceptable? On second thought, neither can we. That is, however, exactly what this person did. We applaud her for her eco-friendly fashion vision, but it’s still weird.

Like, this dress looks as though somebody just fished hit out of the ocean, or as if it were the outer side of a house in the suburbs or something like that.
High-End Fashion Is So Weird Sometimes
We don’t know what the deal is with all those high-end, super fancy-schmancy, we’re tempted to say pretentious fashion events, but they somehow always feature some incredibly strange, totally unwearable pieces of clothing that no sane person would ever think of wearing on a day-to-day basis. And yet, maybe that’s exactly the point – to see what kind of wacky stuff we can come up with that could pass as clothing.

If so, maybe we should stop viewing these events as the peak of everyday fashion, and start seeing them more like elaborate pieces of performance art or something like that.
It’s Football Season!
Go Packers! Or something. Whatever. We’re not too big on football. Do you know who is big on football, though? This gal right here. Don’t believe us? Well, maybe this photo of her dressed in a football-themed dress will change your mind. We would roast her for wearing this if it weren’t actually really funny. Like, it’s obvious that this person’s got a good sense of humor. We can’t roast her for that.

On the other hand, maybe she isn’t joking, and she genuinely adores that football dress. If that’s the case, then we definitely don’t have the heart to roast her. You do you, girl!
Artsy Fartsy Much?
This one is actually kind of beautiful, but not in a “this a dress I’d wear on a day-to-day basis” kind of way. It’s pretty in an “I dressed up as a gothic, arthouse flower for Halloween and nobody really understood the costume” kind of way, which is the best kind of pretty in our opinion. On second thought, maybe we should start normalizing dressing this way. Like, why not?

Maybe all those prestigious fashion events and runways were good for something after all. Like, we definitely wouldn’t have come up with this evil flower look totally on our own.