When Bras And Buttons Fail: The Best (Or Worst) 'Awkward' Wardrobe Malfunctions

Because Jenna’s prom-night dress disaster brought back so many memories.

A good outfit can give you a sense of resolve, help you cultivate a style identity and encourage you to harness your artistic inclinations. A bad outfit will usher you out of your prom in a deluge of tears that could fill an aquifer.

On Monday night’s "Awkward" episode, prom queen nominee Jenna Hamilton thought she had her senior year’s final dance all figured out…until, that is, she accidentally spilled a cup of red wine all over her white dress. Rather than panic, though, Jenna and Tamara called in the big guns to help them find another gown at the 11th hour, and when Jenna tried on a garment they managed to unearth, it fit like a glove.

Unfortunately, it fit like a glove dreamed up by Vera Wang, and almost immediately upon entering the dance, Jenna realized she looked like PHHS’ own shotgun bride. She and T tried to hack away at the hem to make it more modern, but it was no use, and eventually, they packed it in, cut their losses and abandoned ship.

Jenna’s Wardrobe Waterloo was bad, but thankfully, she’s just a needle in an ‘Awkward’ haystack. Take a look back at some of the show’s most memorable wardrobe malfunctions below, and see if Jenna can get herself out of this mess Monday night at 9/8c!

  1. Save Val (Vag) T-shirt

    In an act of solidarity with Val, who was on thin ice with the Palos Hills’ school board in Season 3, Matty and Jenna designed and ordered a collection of “Save Val” T-shirts to wear at the guidance counselor’s hearing. Unfortunately, the “L” was lost in translation, somehow became a “G” and, well, you can guess what happened next.

  2. Jenna bares it all

    When Sadie sent an image of Jenna topless in the locker room around campus, Jenna instantly became the school’s laughing stock. Rather than lay down and take the abuse, though, she decided to become the master of her fate, and flashed passersby to prove she was in control. Unfortunately, she flashed a little bit more than she meant to.

  3. Sadie’s obstinate outfit

    As part of a Palos Hills pep rally, Sadie and Jenna were challenged to exchange outfits with two of their male peers, and the fastest team would be deemed the winner. Unfortunately, Sadie had some trouble assuming her new look and was forced to accept a very distant second place.

  4. This sweater doesn’t go with these facial piercings

    If Tamara thought showing up to a Halloween party without a costume was a faux pas, she was in for a real surprise when — later in the night — a stranger’s…face ring?...got trapped in her sweater. Push, pull, tug, twist — it didn’t matter. The objects might as well have been super-glued together, and the ladies spent the better part of the evening by each other’s begrudging sides.

  5. Lissa can’t come undone

    Not that Jake showed a lick of interest in Lissa’s “behymen,” but even if he had, her bathing suit top was tied more tightly than a series of Lariat Loops at Scout Camp. Maybe consider Velcro next time…?