5 Taylor Swift Award Show Outfits That Totally Missed The Mark

Taylor Swift is a fashion icon. She not only knows how to rock a trend the right way, but also has street style to die for. Like a lot of stars, though, she doesn't always quite get it right. In fact, the "Fortnight" hitmaker has admitted she's changed her style over the years after wearing some questionable pieces. 

"I think that as much as you should be creative and experiment, there are certain things I know are fads, and so I try to steer clear of most of the obvious ones," she told ASOS magazine in November 2014 (via Glamour). "I play the tape of my life forward and don't wear the things that my kids or grandkids will make fun of me for wearing, [like] 'Wow, cool, Mom, cool cowboy boots that you were wearing constantly in 2006!'" she joked.

It may not happen often, but more than one Taylor Swift outfit has missed the mark. Addressing it may be delicate (isn't it, isn't it?) but these looks could have done with a little more thought.

When Taylor Swift attended CNN Heroes: An All-Star Tribute in 2008, she wore a silky black-and-white Trina Turk dress. It was certainly classy, but added about 10 years to her age — she was only 18 at the time! We get that she wanted to dress appropriately for a night honoring inspirational people, but Swift looked more like she was about to walk onto the set of "Suits" than into an award show. Her open-toed black stilettos further cemented the business attire aesthetic, as did her sensible bun and plain clutch. Swift was in her "Fearless" era at the time, and this couldn't be further from the cute, youthful looks she rocked around then.

Taylor Swift attended the 2014 MTV Video Music Awards in a controversial Mary Katrantzou playsuit that just wasn't flattering. We love that she tried to do something different and wasn't afraid of color, but the super short cut created an unfortunate gather at the crotch and looked more like a modest swimsuit than a red carpet outfit. Peep toe heels were trendy at the time, so we can't blame her for giving these Elie Saab shoes a go, but they did nothing to elevate the one-piece. They cut off Swift's naturally long legs at the ankle, whereas a cute pointed court shoe would have helped elongate her legs even more.

We've seen Taylor Swift dressed to the nines on the red carpet over the years, which is why her 2006 Academy of Country Music Awards look was so underwhelming. The then up-and-coming country star hit the red carpet in a BCBG Max Azria dress with a mix of patterns and cowboy boots. The shoes felt authentic for the time, but seeing as this was Swift's debut appearance at the country music awards, we're surprised she wore such a casual daytime sun dress with no real glitz or glam. Three years later, she returned to the awards in a jaw dropping floor-length red gown by Angel Sanchez, which was way more appropriate.

When Taylor Swift walked the red carpet for the 2009 Country Music Association Awards, the color of her outfit just didn't work. The Collette Dinnigan mini dress was cute, glittery, and very in keeping with her sparkly style, so it makes total sense why she picked it. However, the muted gray was too cool to add a healthy warmth to her skin tone and, coupled with her blond locks, Swift appeared washed out. We think this could have been saved via a necklace with a statement jewel, such as an emerald, to warm things up.

The 2010 Met Gala theme was "American Woman: Fashioning a National Identity," but we didn't get that from Taylor Swift's dress. Though she looked gorgeous in her Ralph Lauren Collection white gown, the overall ensemble missed the mark. The simplistic, floor-length dress – that featured thin straps, drop shoulder lace, and lace ruffles — was too understated for the biggest event in the fashion calendar, which is all about over-the-top outfits (check out Blake Lively's iconic Met Gala looks). We do have to give Swift points for bringing a pop of color with her signature red lipstick, but that wasn't enough to elevate this plain, safe choice.