By Wonderwall.com Editor
September 18, 2021 8:49 am PDT
Wonderwall.com is preparing for the 2021 Emmy Awards on September 29th by looking back at some of the hottest looks in the last few years. Start with this one, which was on many of the worst dress lists in 2015, and read on to relive some of the most unforgettable fashion moments of the annual awards show. Heidi Kulm delivered a major fashion flop in her “Big Bird” dress — Canary Yellow Asymmetric Versace Flock with one sleeve and a light skirt — during the 2015 Emmy Awards. Sadly for supermodels, it’s one of the worst looks in the history of the award show.
Keep reading more memorable Emmy night fashion …
Related: Best Emmy Award Jewels Ever
Do you remember this? I’m still thinking about the gorgeous green gown that Zendaya wore for the 71st Emmy Awards in 2019. The “Euphoria” star surpassed many of the best dress lists of the year. Featuring a sleek, bone-in corset-style bodice, Vera Wang’s dark green design turned into a silky skirt with thigh-high slits, showing off her matching green Brian Atwood heels.
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Kerry Washington unveiled a baby bump at the 2016 Primetime Emmy Awards. The actress wore this sleek black Brandon Maxwell design — complete with cutouts to show off her belly! — While pregnant with the second child.
Lena Dunham arrived from Giambattista Valli to the regrets of fashion followers, layered with pink ombre sweets. The top started strangely with a neckline and was replaced by a frothy tulle skirt. The result was a fashion blunder.
Blake Lively was a style prominent figure in 2009. The “Gossip Girl” star has appeared in this sexy Atelier Versace number. The neckline plummeted, with ultra-high slits on the front, showing off Christian Louboutin with a tanned peep toe.
Iconic! Jennifer Aniston saw every corner of the golden goddess in a strapless Chanel dress at the 2004 Emmy Awards. This was an unexpectedly bohemian choice on TV’s biggest night.
For Jennifer Aniston at the 1999 Emmy Awards, this was another iconic fashion moment, but this time for the wrong reason. The “Friends” star looked sloppy in a Randolph Duke dress that lacked the proper support of the top. To make matters worse, she was dressed in fake dreadlocks. But the candy on her arm was on target. The boyfriend Brad Pitt at the time looked sharp with a black ensemble.
Wow! This Armani Preve pick from the always stylish Sarah Paulson was amazing at the 2014 ceremony. Star’s strapless design was full of tulle with mysterious red polka dot details throughout.
Another crop top! Calista Flockhart arrived at the 1999 Primetime Emmy Awards with this amazing combo. This is a white button-down shirt tied over her nose over a pretty gold floor-length skirt.
“Crazy X-Girlfriend” star Rachel Bloom looked absolutely nice in a black lace Gucci gown at the 2017 Emmy Awards. But that doesn’t make people talk. In a red carpet interview with Giuliana Rancic, six Emmy nominees revealed that she actually bought the dress from the rack — “Gucci didn’t lend me the dress! She equipped. “I love it, and I can resell it. I’m in a place where I can afford it now,” she said. “In a previous interview, I said,’Oh, I don’t like size zero, so it can be difficult to find a place to lend a dress,’ but it’s okay because I can afford it,” she said. I advised my viewers at home, “Look at the Real Real of this dress tomorrow!”
Sarah Paulson dominated the red carpet at the 2016 Emmy Awards with a stunning sequined Prada gown with jeweled décor and a plunging neckline, turning envy and completely green! The star of “American Horror Story” proved why she is a respectable fashion force while rocking one of the greatest looks of the annual award show ever.
Ahead of her time! Halle Berry attended the 1999 Emmy Awards for these black glittering coordinates. The upper half featured a cropped spaghetti strap tank with coral embroidery, and the lower half featured a full skirt with subtle glittering embroidery on the top and hem.
In 1992, Cindy Crawford rocked this funky flock at the Primetime Emmy Awards. Black and white dress with bustier bodice, side slit fit skirt, cutouts and long sleeves. She ended it with a strange selection of accessories: a beret.
The sexy open-back dress worn by Calista Flockhart at the 1998 Emmy Awards was simple and stunning. But it also caused rumors that a thin-pinned actress suffered from an eating disorder, which she denied. “I eat. I eat normally. I eat what I like when I want. I don’t have a mess with food,” she insisted on People magazine.
Tracee Ellis Ross was Valentino’s vision at the 2018 Primetime Emmy Awards. The star stood out on the red carpet of the year with this hot pink Valentino number with dramatic oversized sleeves and a full ball gown skirt.
Hot mom! Hayden Panettiere was dazzled by Lorena Salve’s gown with her wide open chest when she was pregnant with her daughter Kaya Klitschko at the 2014 Emmy Awards. This is one of the greatest maternity style moments in Emmy history.
Rainbow stripes aren’t perfect for the classic Emmy look. Patricia Heaton learned this in a difficult way when she appeared on the red carpet in 2004 in this sleeveless multicolor disaster.
It was shocking enough that Sarah Silverman appeared at the 2013 Emmy Awards with a simple LBD instead of a ball gown. But then she dropped a big slaughter: she bought her Stop Staring! $ 60 dress online. “Doesn’t it look as good as the flashy or expensive ones?” She asked E to be memorable! Ryan Seacrest, the red carpet pre-show host.
Everyone was talking about the red dress that Padma Lakshmi wore in 2018. The beauty of “Top Chef” looked bright red in J. Mendel’s gown with a plunging neckline and thigh-high slits. However, Padma wore exactly the same dress a year and two days ago at the 2017 Vogue India Women of the Year Awards in Mumbai. “In this era, I think we should stop sending the message to young women and girls that we all have these endless closets that we will never wear, especially on red rugs. All the strength and gorgeous fabrics are worth wearing again and cherishing. It seems a waste not to enjoy these dresses, “she told People magazine that she decided to wear the same gown twice.
At the 2012 Emmy Awards, Sofia Vergara flaunted the Colombian curve with this extraordinary aqua-decorated Zuhail Murad mermaid dress. The gown was certainly gorgeous, but what really talked about people was the decision of the “Modern Family” star, who revealed on Twitter that he had bust the zipper in the middle of the show.
TV’s biggest night crop top? !! Jaws fell when Gwyneth Paltrow appeared at the 2011 Emmy Awards in Race Black Pucci Separate.
January Jones surpassed many of the best dress lists after the 2010 Emmy Awards in this bold blue Versace gown made up of silk satin petals. In the years since she wore this unforgettable futuristic flock, it has become one of the most instantly recognizable looks of an annual event!
The Marquesa gown worn by Olivia Wilde at the 2009 Emmy Awards is virtually legendary. The warm-up, open-back dress featured an actress’s torso and a thin panel that meandered across one waist.
Eva Longoria took a great fashion risk when she arrived at the 2008 Emmy Awards in a knee-length Marquesa dress with a large ribbon and fringed skirt throughout her bodice. It may not have been the best look of the day, but it was certainly the most memorable!
Hayden Panettiere was talked about for all the wrong reasons when he wore this shapeless iridescent Marc Bauer gown at the 2007 Emmy Awards.
Heidi Klum had a big moment in maternity wear while wearing a red Michael Kors gown and showing off the pregnancy curve (and small legs!) At the 2006 Emmy Awards. She was pregnant with her fourth child, daughter Rusamuel, at the time.
Who can forget when Charlize Theron channeled the flapper girl at the 2005 Emmy Awards? The Oscar-winning actress showed off her stalks at the Chanel Shift of Beads on the biggest night of television.
At the 2003 Emmy Awards, the great late Joan Rivers looked more like a little chick resting in a feathered nest than a host on the chic red carpet. I said there!
Jennifer Garner looked modest and elegant in a strapless ivory Narciso Rodriguez gown during the 2002 Emmy Awards. This timeless look still fits on the red carpet, as it did nearly 20 years ago.
The most unforgettable fashion moment of the 2001 Emmy Awards actually took place during the show, not the red carpet. Ellen DeGeneres had the thankful job of hosting a ceremony less than two months after the 9/11 terrorist attacks, but disguised Björk’s iconic swan dress from the 2001 Oscar. ..
Sarah Jessica Parker shook the wings of many fashionistas when she wore a pink feathered ballerina dress from Oscar de la Renta at the 2000 Emmy Awards and wore a corsage armband. Fashion commentators may have disliked this look at the time, but it’s now one of the most iconic award show fashion moments to date.
The Emmy Awards are now Gothic! The look of this black Armani with a thin overlay was the best choice from Lena Headey at the 2012 Primetime Emmy Awards.

