15 Of Taylor Swift's Biggest Fashion Fails

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Taylor Swift is a global superstar who has been able to make a name for herself in both the singing and acting world. Taylor has become most recognizable for the fact that most of her songs are based around issues in her personal life that have since given her a huge amount of media coverage. Taylor moved to Nashville, Tennessee when she was just 14 years old to pursue a career in country music, but Taylor has since been able to evolve along with her music.

Over the past decade, Taylor has won a number of awards for her incredible career in music, including 10 Grammy awards, 19 American Music Awards, an Emmy Award and a Brit Award. As well as this, by the beginning of 2016, Taylor had sold more than 40 million albums and 130 million singles downloads, which shows how much her music has affected her audience.

Even though Taylor is a recognizable star all over the world and someone who has been linked to a number of well-known celebrities over the past few years in her personal life. It seems that even someone as fashionable as Taylor has bad days when it comes to her fashion sense. The star has been named a number of times on the worst-dressed list at events she has attended as well. The following list looks at just 15 of the worst outfits that Taylor has been seen out in public in. These are some of the biggest fashion fails of her time in the spotlight.

Cowboy Boot Obsession

Taylor Swift turned up to the 2007 American Music Awards thinking that she probably looked great because she had matched her knee-length black dress with her usual cowboy boots, but this was another outfit that saw Taylor hit the worst-dressed list.

The country singer had a serious obsession with cowboy boots in her earlier career, which meant that she would try to pair them with everything she wore, whether she was on stage, on the red carpet, or just spotted outside in public. Thankfully, this obsession became less compelling when she evolved out of country music, but it seems that there are still a number of photos of Taylor in her early career that prove that this obsession was so painfully real. Taylor would never wear an outfit like this on a red carpet in 2018, so it seems to also prove that not only has Taylor's fashion sense changed, but trends in general have as well.

Taylor Knows How To Stay Warm

When Taylor isn't rocking cowboy boots to red carpet events, it seems that she is showing the world the most effective way to stay warm, which is in this long coat that looks very comfy, but probably isn't very practical.

Taylor decided to pair this potentially heavy wool coat with black boots that just don't seem to go together. It seems that in the early 2000s when the rest of the world was experimenting with their fashion sense, Taylor decided to see if it was possible to wear the world's longest coat. The frumpy material of the coat does nothing for Taylor's small frame and just makes her look she's lost inside it. Luckily, Taylor was only seen in this coat once so it seems that the impracticality of it finally convinced her that it was a bad idea to continue to wear something that long on a regular basis.

Rainbow Reputation

What was Taylor thinking when she wore this outfit for the launch of her Reputation album? It seems that this Taylor wanted to prove that her original girl-next-door image was well and truly gone and this rather vibrant dress and matching jacket from Ashish's Autumn/Winter 2017 collection was the best way for her to do this.

While many Taylor Swift fans thought this was an iconic look and went to some extremes to pick up one that looked similar, it seems that many other people saw this as Taylor wearing a rather strange outfit that she had decided to match with gold heels. It wasn't one of her best ideas, but obviously, she wanted to garner attention for her upcoming album so it seems that the image did exactly what she intended for it to do, which was to get people talking so that her new album was being mentioned around the world as well.

Grammy Award Fail

Taylor made the transition into being a pop star a few years ago and it seems that she marked the occasion by attending the 2016 Grammy Awards with a lot of her outfit actually missing.

It seems that her floor-length skirt had a slit that went a little too far up, as it showed off too much, while her tube-style top didn't look as though it was supposed to be matched with the skirt at all. While Taylor has an incredible figure and toned legs that she obviously wanted to show off, the Grammy Awards were the wrong ones for her to decide to make this kind of statement. Taylor's bob haircut is perhaps the best part of this outfit, but as a whole, all three of these components don't all mix together to create a good outfit, which is why this is added to the fashion fail list.

Feeling Blue

Taylor decided to wear this blue outfit to the 2014 MTV Video Music Awards and it is one of her looks that many fans have a dislike for. It is unknown why Taylor chose to wear an outfit of this kind rather than a traditional dress to walk the red carpet at the awards, but if it was to show off her incredible legs, then we may be able to forgive her for it.

She looks fantastic as ever, but it seems that the shoes and the long sleeved blue and yellow playsuit just don't fit together at all. In fact, an outfit of this kind has no place at an award ceremony, since it doesn't give off the right kind of vibe like a dress usually would. Taylor was taking a lot more risks with her style back in 2014 but it seems that this was a risk that she will definitely live to regret.

Green Envy

Taylor arrived on the red carpet of the 2014 Teen Choice Awards wearing a green cropped dress that she decided to pair with some yellow heeled shoes. Once again, Taylor enjoyed showing off her midsection, something that she obviously worked hard to maintain but this wasn't enough to land her on the best-dressed list.

Light green is something that should perhaps never be paired with yellow; it is a little bit too much colour for one outfit. The material of the dress is slightly questionable as well, but the outfit as a whole just doesn't work. Taylor's skin is glowing and her hair looks fantastic as it seems that she has decided to try something new with it, so it seems this look had a lot of potential if she didn't try to put two bright colours together. This isn't one of Taylor's biggest fashion fails, but it is definitely one that deserves to be on the list.

Country Chick

Taylor Swift first rose to fame back in 2007 when she released "Teardrops on My Guitar," "Our Song," "Picture to Burn" and "Should've Said No." But Taylor first hit red carpets back in 2006 when she would show her country roots by always attending events in traditional country boots as well as showing off her blonde locks in her own curled style.

It seems that Taylor's taste in fashion has definitely improved over the past few years since the singer-songwriter now oozes class when it comes to some of her stunning outfit combinations. But it seems that even someone as connected as Taylor Swift is unable to erase the memories of some of her biggest fashion fails, even though this one was around twelve years ago. Looking at the above image, it's easy to see why Taylor wasn't seen as a fashion icon until much later in her career.

Prom Dress Inspiration

Taylor was just dipping her toe into the water when it came to walking red carpets and attending awards events back in 2008 and it seems that her default option was often the colour purple or prom-style dresses. The singer herself was asked about her worst fashion choices and made a comment about the prom dresses she once wore at many of the red carpet events that she was invited to.

Taylor stated that because she missed her own prom she used it as inspiration for many of the outfits that she wore around that time. She is seen wearing a beige version of this dress in the music video for "Love Story," which was also released in 2008. It seems that Taylor has moved on from the obsession now and not a moment too soon; purple definitely wasn't the best colour for Taylor, as you can see.

What Was She Thinking?

The early 2000s saw a number of outfit fails for a lot of celebrities so we probably shouldn't hold it against Taylor that she was spotted wearing the above outfit. The "Love Story" singer decided it was a good idea to match a knee-length bubble dress with vertically striped tights and heeled ankle boots.

Any of these components worn separately would have made for quite a good outfit choice but it seems that Taylor decided to put a few too many things together and the tights look glaringly out of place. As already stated, during the early 2000s, there were many celebs who made these kinds of fashion mistakes because it was more acceptable then. Looking back, there are many images that Taylor would probably cringe about right now.

Schoolgirl Inspiration

Taylor's fashion on the red carpet has been talked about quite a lot throughout this article, but it isn't just on red carpets that Taylor has had mega fashion fails.

Taylor is pictured here looking as though she has taken inspiration from the whole schoolgirl look when she put together this outfit. The oversized blouse and the grey skirt wouldn't look out of place in a school, but it seems that the added knee-high cowboy style boots that include a heel this time just take the outfit over the edge, not to mention the mustard yellow handbag. Maybe Taylor was still a schoolgirl when she decided to wear this outfit because it's the only excuse that would make sense and explain why she decided to wear it out in public when it wasn't an outfit that even remotely made sense.

Red Suede Boots

There seems to have been an obsession with over-the-knee suede boots over the past few years with almost every female celebrity showing that they own a pair of these sought-after boots. It comes as no surprise that back in 2016 Taylor showed off her red pair when she decided to wear them with a pair of shorts and a long-sleeved white shirt while out in public.

The boots should complement the outfit given the colour, but it seems in this case that the boots just look completely out of place. Taylor has managed to pair the boots with an outfit that they have completely overpowered. Annoyingly, Taylor looks stunning when it comes to her hair and makeup but the outfit and the boots were just the wrong choice to put together with an outfit of this kind, which is why this outfit has made the list.

2016 Met Gala

It seems that not all of Taylor's fashion fails came from much earlier in her career since the above image comes from the 2016 Met Gala where Taylor went for a punk-inspired futuristic silver look and the results are seen above. It seems that this outfit was obviously one that was much better in Taylor's head since she was awarded a worst-dressed accolade for her outfit.

Taylor is in fact wearing a mini dress that was made by Louis Vuitton, which mixed metallic snakeskin with leather and was cut out in all the wrong places. Taylor decided to pair the hideous dress with boots that wrapped up her legs and looked completely out of place, not to mention the fact that she opted for purple lipstick alongside her platinum white blonde hair. It seems that Taylor just had a completely off day because this is one of the worst outfits the singer has ever been pictured in.

Personalized Cowboy Boots

It's been more than a decade since Taylor was pictured wearing her own personalized cowboy boots that she had decided to pair with a flowing blue dress. The evolution of Taylor's fashion has been quite noticeable over the past few years and it seems that back in 2007 the star was most focused on her music than she was her fashion.

It's incredible that at the age of 18, Taylor was able to get away with wearing an outfit like this. Luckily her popularity at the time had already reached such a peak that the star could do no wrong when it came to fashion, and her addiction to cowboy boots was seen as a way for her to always be loyal to her country music roots. However, looking back at some of the outfits she wore with these boots and the fact that she had her own personalized pair is slightly cringeworthy.

Horse Lover

Taylor Swift was spotted back in 2014 in Tokyo leaving Narita International Airport, wearing high waisted black trousers with suspenders, a purple cropped jumper with a horse printed on it, and red ankle boots. It seems that the star didn't think that she would be pictured here and was obviously in a hurry to dress since she didn't think through the outfit choice at all.

The handbag doesn't fit in with the outfit, but neither do the red ankle boots that she decided to pair it with. It seems that there are too many colour combinations in this outfit to be able to make it work and the horse on her woolly cropped jumper just seems to make this ensemble even worse. By 2014, Taylor had been in the spotlight for long enough to know that there are cameras around every corner so this is a major fashion fail on her behalf.

Child-Like Outfit Choice

Taylor is pictured here performing at the 2013 Billboard Music Awards and it seems that her outfit choice led to quite a bit of backlash. Many fans accused Taylor of dressing too much like a child, despite the star being 24 years old at the time. Taylor is seen wearing a pair of high waisted shorts and a sparkling unicorn t-shirt as she performs at the event.

It could be argued that the star has a strange sense of style, as has been discussed throughout this article, but this could easily be seen as one of her worst choices. Wearing something like this at a televised awards event was always going to gain her some backlash but it seems that Taylor is a big enough star that she can get away with wearing something like this, even though no one else in her position would ever be able to.