The black-tie extravaganza, which raised money for the Costume Institute in New York, is attended by the biggest stars in the business who spare no cost on their outfits for the night.
Our reporters - Karishma Dipa (KD) and Masego Panyane (MP) - unpack some of the most outrageous and stylish looks of the night.
Rihanna in a show-stopping multicoloured 3D layered design by Comme des Garçons, paired with thigh high strappy red stilettos.
KD: The pop princess is notorious for her unique style, and she’s never afraid to break all the fashion rules and wear whatever she wants. Although I applaud her for her no-holds-barred approach and for sticking to the theme of the night, “Art of the In-Between”, this look didn’t pay off.
The layers looked clumsy and while she might have been going for an over-the-top look, there were too many elements in play, including the variety of colours on the dress, dramatic make-up and shoes which were too tightly fitted.
MP: Where credit is due, it must be given. Riri’s hair, make-up and dramatic shoe game are insanely on point. The shoes are reflective of the Rihanna we all know and just love to bits - bold, daring and cute all at the same damn time. But the dress, man. I understand that with the kind of the event that the gala is, the dress is a fitting part of the show. I still can’t help but cringe at what I perceive to be its chunky, extra style.
John Legend in a white tuxedo Burberry suit and black pants.
KD: The suave-looking musician, in my opinion, was the best dressed male of the night. He played it safe enough to show up dressed in a tuxedo but took enough of a risk to play around with the classical monochrome trend. The suit was also impeccably well tailored and fit him perfectly while also ensuring that he stood out from his counterparts.
MP: A stylish black and white ensemble. Nice fit, cut is flattering to Legend but the suit’s simplicity also allows his partner, Chrissy Teigen, to dazzle in her outfit.
Kendall Jenner in a barely-there dress by La Perla.
KD: The reality celebrity and model is a rising star who isn’t shy to show off her youthful body. I love that this was the case this year and that she wasn’t scared to take a risk, and choosing to do so in black, a colour which is flattering for all shapes and sizes. However, this naked-dress formal wear left nothing to the imagination and revealed too many body parts at once.
MP: This barely-there ensemble just doesn’t work, okay? Her shoes are lovely, hair could have been slightly more exciting but the dress, no. The material, no. The cut, no. NO. NO. NO. Yes, this is the one time to go risqué, which Jenner has down to its bare necessities, but no. The girl does have a banging body, though.