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The World’s Most Regrettable Haircuts

Those days where you’re feeling bold, strut into the salon, plunk yourself in the chair, and declare that you’re going to completely reinvent yourself? These people should have just stayed in bed on those days…

  1. “The Pigtail Bangs”


Are they… are they dyed green to match his ensemble? The most unfortunately Picture Day moment; recorded for all time.

  1. “The Double ‘Stache”

Handlebar on top, creep ‘stache in the middle, a tiny patch of horror on the bottom. It’s the hair sandwich from hell.

  1. “The Realest Rat Tail”

One of the worst trends of the ‘90s, somehow just got worse. A fine example of someone who took things far too literally.

  1. “The Angular Anomaly”

Wha– what? It somehow manages to have a thousand different lines squeezed into one portrait. Aside from the mysterious laser beam battle happening behind this kid as well as the prison stripes on his shirt (foreshadowing his future?) it’s flat on top, straight on the sideburns (or lack thereof) and flowy in back. DEAR LORD.

  1. “The Emo Charlie Brown”

This guy is infinitely less adorable than our beloved Blockhead. But the hairstyles are eerily similar. It’s like he tried to get Charlie Brown’s look, but failed. Hard.

  1. “The Hairline of Horror”

No. No no no. That’s not how you’re supposed to do it. It’s like his entire head just became a paint-by-numbers where you have to stay within the lines and draw back on some hair for this guy.

  1. “The Bart Simpson”

Has no one else had that sense of deja vu while cringing at old episodes of “Jersey Shore”?

  1. “‘The Simpsons’ Style Redux”

But, really. Who looks in the mirror in the morning and says, “I love that I look like a cartoon character today”?

  1. “The Ginger Pile o’ Poo”

What does that stacked, swirling quality with the plop on top remind you of? Anything?

  1. “The Fruitcake”

This guy: “Who lives in a pineapple under the sea?”

Barber: “Say no more.”

  1. “The Fail Jordan”

You’ve disappointed Michael Jordan, kid. IS THIS WHAT YOU WANTED? IS IT?!

  1. “The ‘I Woke Up Like This’”

Not as “Flawless***” as Beyonce makes it sound, apparently. Especially when you seem to sleep flat on your face at night. Or maybe she just walked to Picture Day past a jet engine turbine?

  1. “The Polka (Dot) Party”

He looks waaay too happy for someone sporting that particular diseased look happening on his head.

  1. “The Scream”

Some barber somewhere spent HOURS on this. And was proud enough to document it via photographic evidence. …Even his hair is crying about it. They’re yelling at this guy to free them from their scalp prison.

  1. “The Crown of Shame”

Don’t wear it so proudly, sir. This is how we crown only the most royal of idiots. He reigns supreme.

  1. “The Escaping Snakes”

Even his eyebrows are trying to run away from him. Can you blame them? Don’t worry… he gathered all those squiggles into a preppy side pony so they can’t wiggle off his head and into your nightmares.