Britney Spears' Most Inappropriate Outfits Yet

For all her fame and success, Britney Spears hasn't had an easy road. From the very first moments of her debut, the pop star was scrutinized over everything from her style and attitude to, eventually, her fitness as a parent. Outlets and audiences alike howled over her public appearances — like Britney Spears' twinning Canadian tuxedo moment with Justin Timberlake — and harshly critiqued the quality of her performances.

Despite all of this, there's no denying that Spears built herself into an industry icon. And with all the subsequent revelations and legal battles that have played out since her early days, the "Oops! ...I Did It Again" singer has definitely earned some grace as we look back over her career and fashion choices. Still, certain outfits seem to stand out as questionable speed bumps in the progression of Spears' signature Y2K style. From the scandal surrounding her breakthrough music video to moments of tone-deaf styling, Spears has worn more than her fair share of inappropriate ensembles throughout the years.

Compared to some modern fashions — and even some other fashions later worn by the pop princess herself — Britney Spears' first head-turning outfit from "...Baby One More Time" is barely a blip on the radar. At the time, though, her sexy schoolgirl look blew up in both good ways and bad, helping rocket Spears to stardom while also earning her derisive nicknames like "little Lolita" (via The Austin Chronicle). Proponents of teenage modesty evidently weren't pleased, and whether or not this look was genuinely inappropriate, it certainly made waves.

Britney Spears has never been afraid to get flirty with bared skin, but that often comes with a side of adorability. Unfortunately, there was nothing cute about her ensemble at the 2002 MTV Video Music Awards. The "Lucky" singer showed up in a confused dominatrix-inspired look that didn't even gel with itself. For one thing, there were too many textures, from the mesh arm-socks and gladiator heels to the scalloped lace slit on the short leather skirt. Worse, Spears did nothing to reimagine the aesthetic, so the effect looked like Party City's tacky idea of a "bad girl" rather than a red-carpet ensemble.

The TRL Awards may not have lasted very long, but we'd argue that any award show demands a certain amount of decorum and effort. However, Britney Spears elected to ignore red-carpet convention for the TRL Awards' inaugural 2003 event, skipping formalwear for a cropped and shredded sweater over a bare midriff and low-rise hippie skirt, all in plain neutrals. Worse still, Spears was actually co-hosting the show in this utterly low-key outfit, which seemed like a random and underwhelming choice for the occasion.

The year 2007 lives in infamy among Britney Spears fans. This was the year of her divorce from Kevin Federline and very public breakdown, from shaving her head to hit-and-run charges. Some celebrities have stunning post-breakup style transformations, but the "Toxic" singer's frazzled headspace seemed to come through in her bizarre fashion choices that year, such as the helter-skelter cover-up she donned during a South Beach visit that May. This outfit had everything from haphazard, asymmetrical straps and gold accessories to a black fedora. The one thing it didn't have: a sense of direction.

Britney Spears' saucy 2009 "Circus" tour was full of fabulous costumes inspired by both the big top and positions of authority. Spears appeared not only as a ring master but also a cop, a military officer, and an armor-plated warrior. It was an ode to female empowerment for the most part, but at least one outfit was memorable for all the wrong reasons. Spears' sparkly, nude-and-black bodysuit mimicked the effect of nipple pasties in a sexualized aesthetic that felt out of step with the theme of her other, stronger looks. Fair play to the star for showing that a mother of two can still rock a revealing, skin-tight bodysuit if she wants to, but with such incredible competition, this was probably the least-empowering outfit of the tour.

Faux pasties weren't the only sartorial trouble Britney Spears got into during her "Circus" performances. This was also the tour that raised questions of cultural appropriation over one of the singer's costumes that was seemingly inspired by Indian culture, which she donned for a Bollywood-style remix of "Me Against the Music." There's a fine line between celebrating another culture and turning it into a caricature, and it's unlikely that Spears meant any offense with the look. Still, it was ultimately too on-the-nose to be written off as an homage.

For more Spears content, read up on how she found herself on our list of celebrity outfits that made us cringe in the past but we love now.