Remember Urban Outfitters' pill bottle-shaped flask and "Navajo hipster panty?" We wish we didn't. And yet somehow, despite all the bureaucracy required to take a retail item from conception to shelves, retailers still manage to green light offensive items, inciting widespread backlash and leaving PR departments scrambling to issue apologies.

Here are some of the most memorable headline-making incidents that have left apparel companies in hot water over the years:

1. H&M
Earlier this summer, Swedish chain H&M came under fire for selling fake feather headdresses. Supposedly crafted with summer music festival attendees in mind, the items were pulled from five stores in Canada after complaints that the headgear was tantamount to cultural mockery. If only H&M had done a quick Google search, the retailer would have noticed the trouble Victoria's Secret got into when it sent supermodel Karlie Koss down a runway in a Native American-inspired headdress.

2. Nike
In its quest for edgy, eye-catching design, Nike is no stranger to overstepping boundaries. Most recently the brand found itself at the center of controversy over a pattern on women's tights that closely resembled a traditional Samoan tattoo reserved for males. The Pacific community found the design exploitative, resulting in the retailer stopping production. And in putting out another product, it seems the sportswear brand needed a brush-up history lesson. Aiming to appeal to Ireland's national pride on St. Patrick's Day, Nike produced a line of black and tan sneakers intended to reference the popular drink made from mixing stout and lager. Unfortunately, "Black & Tans" is also the name of a violent British paramilitary group that targeted civilians during the Irish Revolution.

3. JC Penney
Once considered one of the tamer of the big-box department stores, JC Penney has found itself at the center of controversy numerous times over the past few years, for one reason — a revolving door of CEOs, for example — or another, like a girls' shirt that read, "I'm too pretty to do HOMEWORK, so my brother has to do it for me." Mommy bloggers were in an uproar over the top, which added insult to injury by spelling out the phrase in colorful bubble letters and juvenile cursive across the front. Two hours after a petition went up on, sale of the shirt was discontinued from the store's website.

4. The Children's Place
In another example of not learning from competitors' mistakes, parents were less than pleased with the messages The Children's Place was sending to girls with shirts it featured earlier this month. The most offensive of the bunch, which has since been discontinued, listed "My Best Subjects" and included "Shopping," "Music," "Dancing," and "Math," with boxes checked next to all subjects except "Math." At the bottom of the shirt it said, "(Well, nobody's perfect)." Parents bristled at the shirt's implied sexist message, which echoed the infamous, inflammatory Barbie recording from the early '90s that declared, "Math class is tough!"

5. Abercrombie & Fitch
Prep-style standard-bearer Abercrombie & Fitch could go head-to-head with Urban Outfitters to determine which retailer has produced (and pulled) more rabble-rousing merchandise over time. Most recently, irate Taylor Swift fans rallied to have the store remove a T-shirt that read "#more boyfriends than t.s.", referring to the seemingly-always-changing male companions in the singer's personal life. While the Taylor Swift tee might have drawn the ire of a niche demographic, in the past, Abercrombie & Fitch has produced some other absurdly offensive tops. Two shirts for females in 2005, for example, had the phrases "Who Needs a Brain When You Have These?" and "Gentlemen Prefer Tig Ol' Bitties" emblazoned across the chest.

6. Macy's
In an attempt to appeal to Latina shoppers back in mid-2007, Macy's printed T-shirts with the unfortunate catch-phrase "Brown is the New White." The shirts definitely attracted the attention of the target demographic, though, with Hispanics voicing offense at the suggestion that they should strive to be or pass for "white."