The Most Offensive Clothing Items Ever Made

After initially defending a new line of custom basketball sneakers that connect to the foot via way-too-reminiscent-of-slavery ankle shackles, Adidas finally pulled the shoes off the market. About time. It made us wonder, were the Shackle Shoes — slammed by Jesse Jackson as a “gross insult” — the most offensive article of clothing ever released?

They’re definitely up there. But between JCPenney’s sexism and Urban Outfitters’ racism, Adidas has some stiff competition. Here’s our list. Agree? Disagree? Have some vintage threads in your closet that’d put all of this to shame? Weigh in below.

1. Urban Outfitters’ Star of David shirt

In late April, Urban Outfitters released a tee featuring a star graphic that looked way too close to what Jews were forced to wear in Nazi-occupied Europe. You know, the symbol used by the Gestapo to determine who would die in ghettos and concentration camps. The shirt is still sold today — just without the star, and for half the initial price of $100.

2. JCPenney: “I’m Too Pretty to Do Homework”

WHO HAS TIME TO DO HOMEWORK WHEN THERE’S A NEW JUSTIN BIEBER ALBUM OUT??!?! Not JCPenney, who could have easily done the research to determine that the year was not 1951. The company mercifully pulled the shirt from stores and online.

3. Urban Outfitters: Ghettopoly

Clutch Fans

Not clothing, but this gets a nod for just being a f***ing ridiculous thing to stock in a clothing store. In 2003, UO sold a board game called Ghettopoly, which featured “playas acting like pimps and game cards reading “You got yo whole neighborhood addicted to crack. Collect $50.”

4. Urban Outfitters: “Eat Less”

Hey, guess who! Urban’s controversial 2010 offering was a shirt, pictured on a skinny model, emblazoned with the words “EAT LESS.” Awesome message to send teenage girls, Urban Outfitters.

The Frisky noted that just months before, Urban had a plain T-shirt whose color was described as “Obama/Black.” Amelia McDonell-Parry said what we were all thinking: “You know what I want? Urban Outfitters to STFU.”

But the company was just concerned about its customers’ health, right? Right.

5. Abercrombie & Fitch: Rick Shaw’s

Oocities

Though A&F’s Asian-inspired T-shirts were meant to be funny, the stereotypical images of Asians with caricatured faces and slanted eyes weren’t amusing to any Asian-Americans.

6. Abercrombie: Thongs for kids

In May 2002, Abercrombie expanded their market for underwear to include sizes for children ages 7 to 14. The undies had phrases like “Eye candy” and “Wink wink” on the front. The move shocked consumers and pissed off mothers everywhere.

7. Urban Outfitters: Palestinian violence tee

Chic and Untroubled

UO really has a knack for insensitivity, doesn’t it? The American Jewish community was outraged over a shirt that seemed to support Palestinian violence. Stay out of politics and stick to fashion, Urban Outfitters.

8. Abercrombie & Fitch: “Who Needs Brains When You Have These?”

Hermansaksono

Abercrombie, done with pissing off moms, then focused its attention on insulting teenage girls. Some young women held a boycott of the store’s sexist tees.

Other slogans included phrases like “Do I Make You Look Fat?” and “Gentlemen Prefer Tig Old Bitties.”

9. American Apparel: “Teenagers Do It Better”

Gothamist

After AA CEO Dov Charney’s multiple and well-publicized lawsuits involving sexual harassment of his young employees and models, this shirt scores high on the creep factor. The item, a collaboration with Ey! Magateen (celebrating “the magnificent vitality, energy and power of young male adulthood” and featuring 16-year-old models), is still sold online.

10. Urban Outfitters: the “Navajo” line

Jezebel

After getting in some legal trouble for their use of the word “Navajo,” the company found a way around the issue altogether — changing one letter in the word. The items remain in the catalog, but instead of a Navajo skirt, you can now get a Navado skirt.

BONUS: What the hell is this?

Mallory Kathleen