The American singer, songwriter, rapper and actress Kesha is probably known just as much for her unique and weird outfits as for her music. Back when she had just started her career her outfits were often criticized and the singer herself was often placed in the worst dressed celebrity lists.
Back then Kesha was all about glitter, animal prints and gold. Her outfits were ridiculous and cringy but they were also attention grabbing and unique. They were not great or chic or elegant but at least they spurred talk and gossip.
In terms of fashion, the singer has come a long way since then. Nowadays her outfits are much more stylish, chic and unique, so much so that she has become one of the newest style icons whose looks are to be emulated, not laughed at or made fun of.
The list below consists of Kesha’s best and worst looks. For the most part her worst outfits come from years ago which gives us hope that the singer has developed a sense of style. Her best looks tend to come from New York Fashion Week.
20 Fashion Forward - A Stunning Black Dress
We’re so used to seeing Kesha attending formal events wearing the most ridiculous and bizarre pieces that when eventually she does show up wearing something we deem “normal” we can’t help but applaud the quirky singer.
For example, take this dress that Kesha wore at the 2014 Billboard Music Awards. It is a stunning black and cream dress and it looks absolutely fabulous on the singer. The dress is rather tight-fitting but because its bottom is wide and flowey. It looks wonderful.
Kesha opted to forego all accessories when wearing this dress, instead letting the dress speak for itself.
19 Forgot To Use A Mirror - Dress Shorter Than Her Braid
This outfit, worn by Kesha at 2010 MTV Video Music Awards, wouldn’t be that bad if Kesha’s dress was slightly longer. The outfit, which consists of a mini black leather dress, black heels, a silver clutch and silver earrings is quite tasteful except for the fact that the singer’s dress is obviously way too short.
For this look the singer opted to put her hair into a long braid which is actually longer than her dress. As far as Kesha’s outfits go, this look isn’t terrible but it is certainly not great either. We certainly hope that the singer can avoid such short dresses in the future because they’re neither chic nor sexy.
18 Fashion Forward - A Chic Black Dress
Kesha wore this edgy but chic black dress while attending World Premiere of Disney’s film Planes: Fire & Rescue at the Al Capitan Theatre in Hollywood, California.
The long-sleeved black dress has silver studs on it and comes slightly above Kesha’s knees, which allows the singer to showcase her beautiful, long legs. Kesha paired the dress with black heels and rings, foregoing all other accessories that may take away from the outfit.
Kesha also left her purple hair down which she had styled in waves. We must admit that the singer looked amazing at this event.
17 Forgot To Use A Mirror - A Sparkly Rainbow Cape
This outfit is possibly one of the worst outfits ever worn by Kesha. In fact, we’re not even sure what the outfit consists of but we’ll try our best nonetheless.
As far as we can tell, the outfit consists of sparkly pants, an electric blue shirt, a light blue eagle brooch, a weird sparkly cape, and silver shoes. Kesha wore this rather ridiculous outfit at 2017 MTV Europe Music Awards at Wembley Arena in London.
The singer certainly stood out from the crowd with this unique look but we’re not sure that it looked that great on her.
16 Fashion Forward - A Quirky Look For Banana Republic Collection Launch
Kesha wore this stunning outfit at Banana Republic L’Wren Scott Collection Launch. The singer’s outfit consisted of a floral green skirt, a black crop top, a stripy shirt which the singer wrapped around her hips, a denim jacket and knee length black boots. The singer’s rainbow colored hair was left down in waves.
Kesha decided to forego all accessories understanding that adding jewelry may take away from the outfit rather than add to it. We love this particular Kesha look because it’s quirky and unique but not sleazy and weird. We hope that she opts for more outfits like this in the future.
15 Forgot To Use A Mirror - Awful Gold Dress
This is not a bad outfit and in fact may even look good on someone else. However, it looked absolutely terrible on Kesha. The above outfit consists of a gold dress, black shoes and accessories such as earrings and rings.
For this particular look Kesha opted to keep her hair down and wore quite heavy makeup, particularly around her eyes. For some reason the gold dress looked terrible on the singer and suited neither her body type nor her skin tone, which is a shame because with the right dress Kesha would have looked stunning.
14 Fashion Forward - All-Black Outfit
You have to admit that the quirky singer looks pretty amazing in this all-black outfit. Kesha wore this outfit at 2015 New York Fashion Week and looked absolutely fabulous. The outfit consisted of a black velvet dress, a black furry coat, a black hat and black boots.
The singer’s blonde locks were left down in her signature waves and her makeup was minimal which complimented her chic outfit perfectly. While we’re somewhat surprised that Kesha opted for this all-black outfit (after all, she is usually seen sporting mad colors and patterns) we are incredibly glad to see the singer toning down her look.
13 Forgot To Use A Mirror - Leather Bodysuit
This is an awful outfit that Kesha opted to wear for her performance in Las Vegas in 2013. The outfit consists of a black leather bodysuit, black leather knee length boots and a black and brown cape. For this particular look Kesha decided to keep her hair down and opted to forego all accessories.
Only a year later, Kesha revealed in a Vogue interview that her style has changed significantly – “I look back lovingly because I was having so much fun [with hair and makeup]. There was a time I went on the red carpet with a Mohawk, but I’ll probably never do that again. And before I went on stage I used to pour beer on my body [as an adhesive] then roll in a bathtub full of glitter. I don’t do that anymore because it irritated my skin.”
12 Fashion Forward - Black Sequin Jumpsuit
This is another amazing look that the singer sported while attending New York’s Fashion Week in 2015. You have to admit that Kesha looked absolutely stunning in this incredibly chic but at the same time unique and quirky outfit.
Kesha’s outfit consisted of a white sweatshirt, a black playsuit dotted with sequins, white heels and white shades. As always, the singer left her blonde locks down in her signature waves and opted to forego all accessories and jewelry and let the outfit speak for itself.
This is a pretty unique look that is at the same time both casual and formal and we can’t wait to steal it from Kesha.
11 Forgot To Use A Mirror - Staff Fit For A Voodoo Ceremony
Kesha wore this ridiculous outfit to the 21st Annual Much Music Video Awards in Toronto in 2010. While her outfit wasn’t that bad if you choose to ignore the weird staff that is probably more suited to a voodoo incantation than a music award ceremony, it is still quite awful and therefore deserves to be on this list.
The above outfit consists of a black shirt, black shorts, black shoes, black hat and of course a strange looking staff. The outfit certainly looked too casual and strange for such an event and we do hope that the singer opts for something different next time.
10 Fashion Forward - All-Pink Outfit For Fashion Week
Kesha clearly kept all her best outfits for New York’s Fashion Week. This is another amazing look that the singer showcased at Fashion Week. Her outfit consisted of a baby pink skirt, a pink bra, a baby pink see-through top, a baby pink coat, white heels, a white clutch and unique pink shades. As always, Kesha left her hair down and opted to forego all accessories.
You have to admit that the all-pink outfit looked absolutely amazing on the singer and we truly hope that she will opt for similar outfits in the future. Who knew that Kesha had a great fashion sense after all?
9 Forgot To Use A Mirror - Mannequin's Head As An Accessory
Kesha wore the above bizarre outfit to the KIIS FM’s Wango Tango Concert at the Staples Center in 2010. Her outfit consisted of a black shirt, black shorts, black heels, shades, a black fur coat and... a mannequin’s head!
We know that Kesha likes to surprise us with her odd looks but we think the above outfit is a bit much. It is however worth remembering that the above look is all the way back from 2010 and Kesha did talk about how her style has completely transformed in a Vogue interview in 2014. Thus, there is still hope yet that Kesha will no longer stun us with extremely bizarre outfits such as the one above.
8 Fashion Forward - Chic Black And White Checkered Dress
We are both perturbed and frightened by the fact that Kesha’s best outfits were worn by her at New York fashion week. Does that mean that the quirky, animal print loving singer only made a concession to her overall style during the New York fashion week? Or has her style truly been transformed?
We seriously hope that the latter is the case! Here we can see another amazing outfit that Kesha wore during the New York Fashion Week. The outfit consists of a black and white checked dress, a black blazer which was slung casually over the singer’s shoulders and black knee length boots.
7 Forgot To Use A Mirror - Splattered In Paint
Kesha wore the above outfit at the MTV Europe Music Awards in 2010 at La Caja Magica. The outfit consists of an electric green bodysuit, electric green socks, and black boots. Furthermore, the singer has spray paint all over her body, face and hair.
There’s no denying that this is one of Kesha’s worst outfits ever. It looks neither stylish nor innovative and we must admit that it truly disappointed us because it showed us that the singer has no style whatsoever.
Still, Kesha has come a long way in terms of her style since 2010 so hopefully we will never have to see outfits like the one above ever again.
6 Fashion Forward - A Chic Ensemble
Here we have another amazing outfit that Kesha wore at New York Fashion Week. It seems that the singer really went all out in 2015 to stun everyone with her amazing fashion sense. Here’s to hoping that she keeps it up and continues to amaze us with her unique and chic outfits!
The above stunning outfit consists of a blue and white dress, a baby pink overcoat, white socks, maroon shoes, a baby pink hat and cool shades. The singer left her hair down and opted to forego all accessories. You have to admit that this is a pretty stylish look!
5 Forgot To Use A Mirror - 90's Inspired Outfit Gone Wrong
Kesha wore the above outfit to the MTV Movie Awards in 2013. The outfit consisted of pink flowy patterned pants, a patterned top, a black throw and a black hat. For this look Kesha wore rather heavy makeup including a bold lip.
This outfit is generally deemed as Kesha’s worst outfit ever and it is generally believed that for this look Kesha combined all the worst 90's trends. There’s no denying that the above outfit is truly awful and once again it proves that Kesha has no taste, or at least, that she had no taste back in 2013.
4 Fashion Forward - Simple But Chic
This is probably one of Kesha’s simplest and most chic outfits ever. The quirky singer wore this elegant outfit during New York Fashion Week in 2015 and looked pretty amazing. Her outfit consisted of a simple black shirt with a white collar, a white skirt and white heels.
Kesha left her hair down in her signature waves and decided to forego all accessories and jewelry so as to let the outfit speak for itself. Her makeup was simple and elegant which complimented her outfit perfectly. This is another one of Kesha’s outfits that we will probably steal.
3 Forgot To Use A Mirror - Patriotism Taken Too Far
Kesha wore the above outfit to the 2013 RIAA Presidential Inaugural Charity Benefit. For the event Kesha wore a red Paul & Joe suit, Lublu blouse, Justine M. Couture headband, Desla bracelet, Dolce Vita shoes, a number of rings and a Gabriela Artigas necklace.
Kesha tweeted that morning saying – “wearing it proud ❤ U$A” and “Obama became 1st president to address gay rights during an inauguration speech. Proud to have a president who believes We R Who We R.”
However, while her outfit may have been fitting for the occasion many couldn’t help but think that it looked too much like a costume.
2 Fashion Forward - A Cute White Dress
We truly don’t understand why Kesha chooses to wear ridiculously bizarre outfits when she looks so good in chic and elegant ensembles. Take this above look for example. Kesha wore this outfit to the 9th Annual Delete Blood Cancel Gala in New York and looked absolutely stunning.
The singer’s outfit consisted of a cute white dress that suited her perfectly. Kesha left her hair down and opted to forego all accessories and jewelry. Her makeup was simple which complimented her outfit nicely. We wish Kesha always dressed this chic – when she wants to, the singer can be a real style icon!
1 Forgot To Use A Mirror - Baby Pink Suit
There’s no denying that the above outfit is one of Kesha’s worst looks ever. The above outfit consists of a black lacy bra, a pink patterned shirt, purple shoes and a baby pink trouser suit that has colorful and quirky patches sewed onto it.
The above look did not suit Kesha's body type at the time but it shouldn’t have been an excuse for haters to criticize the singer either – “I’ve had a lot of ups and downs. It’s been quite a journey. I went to a dark place. There was a lot of not eating—and I started to think being hungry to the point of feeling almost faint was a positive thing. The worse it got, the more positive feedback I was getting. Inside I was really unhappy, but outside, people were like, “Wow, you look great.”
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