1. Jennifer Lopez, 2000
Yes, this is that dress. J.Lo walked the red carpet in 2000 in her now-iconic Versace dress that featured a dangerously low front, and was held together by gilded safety pins.
It was revealed earlier this year that this dress prompted the creation of Google Images, because people kept searching for this on Google’s website.
2. Joy Villa, 2015
If awards ceremonies are about the best couture, Joy Villa likes to take the other route, with the most head-scratching looks. Here, she shows up in a dress that can only be described as “construction site couture”.
3. Joy Villa, 2017
Proving once again that she doesn’t take red carpets too seriously, Joy Villa stole the conversation again when she showed up in a “Make America Great Again” dress. Adding more question marks to the look, the back of her fishtail featured President Trump’s name boldly sequinned.
4. Destiny's Child, 2001
Before Beyoncé became the full-fledged fashion diva that she is known today, she was a member of the iconic girl group, Destiny’s Child. When they attended the Grammy Awards in 2001, the trio wore matching outfits in forest green lace from Beyoncé’s mother’s fashion line, House of Dereon.
5. Margaret Cho, 2017
Between the massive hair, the dramatic eyeliner or the goth lip colour, comedienne and actress Margaret Cho certainly knew how to make an entrance.
6. Paula Abdul, 1989
Ruffles, that neckline, sequins, and those crunchy curls…Paula Abdul reminds us again why the ’80s had some of the most daring fashions ever.
7. Lady Gaga, 2010
Complete with a matching star accessory (which she carried down the red carpet the entire time), Lady Gaga worked a futuristic dress with towering heel-less platforms and proved that this is a look only she could carry off.
8. Lil Kim, 2002
Lil Kim was the biggest fashion icon of the ’00s, because she paid no attention to the critics and her brand of unapologetic music and garish, gaudy fashion won her fans all over the world. Here, she races down the red carpet in a racer-inspired outfit complete with a Chanel-branded motorcycle helmet.
9. Madonna, 2015
Pop’s Material Girl a.k.a. Madonna proved that even at 57, she could rock a scintillating outfit. While the back of her outfit provided her with her share of wardrobe malfunctions, there’s no denying that Madge is rocking this look with aplomb.
10. Annie Lennox, 1995
This is a look best described as “Minnie Mouse for adults”. You could say that sweet dreams are made of this.
11. Bleona, 2015
We have to hand it to Bleona for wearing a moulded corset with a ruffled train. Imagine the trouble of having to go to the toilet in that! Still, she manages to carry it off, thanks to her confidence and a relatively simple mien.
12. Imogen Heap, 2010
In 2010, indie songstress Imogen Heap walked the red carpet with a parasol, a bubble skirt, a structured collar and ballet flats. If you’re confused from reading this sentence, you’re not alone.
13. Nicki Minaj, 2012
Never one to shy away from controversy, rapper Nicki Minaj brought an actor dressed as the Pope with her, as she slinked down the red carpet in her Versace robe. Okay…
14. Toni Braxton, 2001
The “Unbreak My Heart” singer proves that if you’ve got it, flaunt it. And flaunt, she did.
Receiving her award for “Best Female R&B Vocal Performance” in a white Fifth Element-esque gown that left little to the imagination, Toni was radiant with excitement and confidence despite her risqué dress.
15. Sasha, 2012
Russian singer Sasha Gradiva came out guns blazing to make an impression, and we mean that literally and metaphorically.
While her baby pink gown exuded demure, Old Hollywood vibes, Sasha threw on the most unexpected accessory to complete her look: an armpiece featuring several model firearms.