Horror Stories: Outfits That Flopped At the Office

Apparently there’s no dress code at the offices of Gilt Groupe, the online sample sale Mecca that we are obsessed with, because the founders “adore the personal style of every employee.” From the “blokes” at the warehouse in their Kidrobot tees to the world’s most stylish IT department, members of which teeter around in Louboutin and D&G, from the sound of it, it’s like fashion nirvana over there. [The Huffington Post]

But while site founders Alexandra Wilkis Wilson and Alexis Maybank may be down with all manners of sartorial experimentation, I can think of quite a few times when previous bosses were a tad aghast at my work wardrobe. Like that time I wore five-inch heels to oversee envelope stuffing at a politician’s campaign office. I was totally fine, but all of my coworkers thought it was hilarious for some reason. Lucky for me, I’ve since left political fundraising in favor of a more fashionable line of work and my office outfit mishaps are at a minimum these days. Too bad I can’t say the same for everyone else!

Check out some awesome work outfit horror stories after the jump and let us know if you’ve had any winners (by which we mean losers) of your own.

“Know what’s officially a bad idea to wear in an office full of guys? A sheer blouse. I thought it would be stylish with a pencil skirt but I got a lot of not-so-awesome attention while wearing it.” – Gina

“My office has no dress code, so one day I decided to screw it and wear a puffy party dress with motorcycle boots. I spent the entire day trying not to blush as literally everyone in the office looked at me like I was completely insane.”– Sarah

“I needed to wear my cute new sundress immediately after I bought it last week. Unfortunately, my obsession with the new item prevented me from seeing it for what it was: totally see-through. That was a fun day at work.” – Melinda

“I wore my new wide, really wide-leg, pants to the office last winter and all the guys kept calling me Gumby.” –Lauren

“You know your attempt at boyfriend jeans has gone awry when your boss asks, rather severely, if you bothered to go home and change out of your boyfriend’s clothes before coming into the office. Oops.” – Stella

“I was fresh out of college and started a new job three weeks before Halloween. My boss made a big deal in the Monday morning meeting about how he was going to dress up… He was even going to have a costume contest in the break room and buy the winner lunch. Being the new hire, I wanted to be a team player. So, I prepared an office-appropriate version of ‘Peggy Bundy’ complete with a huge red wig. When I showed up, no one else dressed up, not even my boss. He did however point and laugh along with my other coworkers. I wanted to die, but not in those god-awful costume leggings. And of course, I did not get the free lunch.”– Mindy

Tags: work clothes