Ellen DeGeneres' Fashion Misfires At Awards Shows Over The Years

Ellen DeGeneres is a celebrity generally known for her comedy prowess, longtime talk show, and some interesting controversies here and there. As for her fashion sense, it's arguably not one of her strong suits. Over the years, DeGeneres has stepped out for awards shows, red carpets, and other events dressed in both good and bad looks. But the bad might outweigh the good. 

Even considering how DeGeneres' reputation took a dive in 2020, she has had cause to dress up for the many award shows she has either been invited to or nominated for throughout her career. Her awards shelf at home (or it might be a whole room, at this point) is weighed down by her many accolades. This includes over 30 Daytime Emmy Awards and 20 People's Choice Awards, among others. With this in mind, she's also had to be present to accept most of these awards, which means her stylist has had a lot of work cut out for them throughout DeGeneres' long time in the industry. 

Stylist Kellen Richards was the costume designer and stylist on "The Ellen DeGeneres Show," and she was also behind many of DeGeneres' red carpet looks. Sure, DeGeneres was nominated for several Daytime Emmy Awards for her talk show work, but as for awards show outfits, that's another story. While there were some winners here and there, she had a lot of awards show ensembles that were questionable at best. Here are some of her worst fashion fails over the years.

Not long after Ellen DeGeneres' talk show, "The Ellen DeGeneres Show," premiered in 2003, she attended the VH1 Big in '04 special award broadcast. For the event, DeGeneres tried to go for a more relaxed outfit. But for multiple reasons, it was a major miss.

For starters, she wore a gray blazer with prominent shoulder pads and a red and gold cross emblazoned on the side. She then paired it with loose-fitting jeans that seemed too long for her. It was one of her earliest fashion fails. 

At the more relaxed Teen Choice Awards in 2010, Ellen DeGeneres' outfit should have fit in well, with ripped jeans and preppy sneakers. But she seemed to be holding on to the last vestiges of 2000s fashion with her choice of top.

DeGeneres had on a white and dark blue shirt with huge stripes on it, with a vest on top. The vest style was very popular in the '00s, but we're pretty happy it's stayed there, for the most part. 

By 2020, Ellen DeGeneres truly had her own style figured out, but that doesn't mean that it was always good. She appeared at the Grammy Awards that year in this ensemble with black pants, a black top, and a dramatic bomber jacket on top.

The jacket was gold and black and covered in sequins, with a sort of chain-like pattern all over. While we can admit that the sequins brought a bit of glam that felt fitting for the venue, the jacket was too in your face with the design. 

In addition to winning a few of the trophies over the years, Ellen DeGeneres has won the honor of being one of the worst-dressed celebrities at the People's Choice Awards. Unfortunately, her frequent appearances at award shows have led to several not-so-great fashion moments for the comedian. In 2007, one of those moments happened when she arrived at the PCAs in what looked like tweed pants with a white button-up shirt. 

While those were fine, she decided to complete the ensemble with a velvet blazer and a long, thin black scarf. The scarf is another trend we're glad stayed in the past, because it only made the outfit 10 times worse.

Ellen DeGeneres' love for patterned bomber jackets seems to be a more recent development. In 2017, while presenting an award at the MTV Video Music Awards, she had on jeans, white sneakers, a black shirt, and a black jacket covered in what appeared to be white dove imagery.

It might seem like a simple outfit, but the jacket is clearly the main focal point. We just wish DeGeneres had chosen a different jacket that wasn't eye-catching for the wrong reasons. 

It turns out that Ellen DeGeneres didn't give up on the vest trend in 2010, since she decided to wear it again at the Teen Choice Awards the next year. It's hard to decide if this time around was better or worse.

Instead of the striped shirt underneath, DeGeneres wore a white button-up and added a loosely tied black tie with small white polka dots. Overall, the fit and colors were better than the year before, but the vest was still a hard pass.

While taking home another People's Choice Award in 2009 for her talk show hosting skills, Ellen DeGeneres wore another questionable ensemble. She donned a white shirt with a dark blue cardigan buttoned up on top. 

Although that in itself was a bad choice, she also wore dark pants with pinstripes all over and a bedazzled heart on the left side. Without the heart embellishment, the attire would just be boring and too casual. But the bedazzled design takes it further into the strange.