Celebrities Who Have Broken Anna Wintour's Fashion Rules (and Pulled It Off)

Anna Wintour’s influence over the fashion industry is undeniable. As the Editor in Chief of Vogue U.S., Wintour has spent the last 30 years deciding which trends deserve to grace the pages of her famed magazine and which should be left by the wayside. In some circles, Anna’s opinion means everything, and receiving the coveted "AWOK” stamp of approval can make or break a career. 

Given the fact that Anna’s word counts for so much, it would be logical to assume people would be hesitant to go against her advice, particularly when it pertains to fashion. However, whether it be wearing head-to-toe black or mixing patterns with unbridled flair, we’ve found several examples of celebrities who have (perhaps unwittingly) broken Wintour’s fashion rules and managed to prove that rules really are made to be broken. 

Whether it was intentional or not, this is an ode to the risk-takers of Hollywood who have proven it is okay to play by your own style rules. Scroll through below to see four times celebrities have successfully broken Anna Wintour’s fashion rules. 

Rule 1: Never Wear Head-to-Toe Black

One of Wintour’s most famed fashion commandments is to avoid wearing head-to-toe black. In a recent segment of the Go Ask Anna video series, Wintour was asked how to spice up an all-black outfit, to which she responded simply: "Just don’t wear all black—it seems too gloomy and as if one is going to a funeral.”

One celebrity who often defies this rule is none other than monochrome maven, Jennifer Aniston. The actress regularly wears entirely black outfits and manages to make it look interesting every single time.

Shop Jennifer's Look 

Rule 2: Beware of Mixing Prints 

Despite the fact Wintour often wears patterns herself, the Editrix warns that people should be quite wary when it comes to mixing prints or patterns, particularly, those of us who may be of smaller stature. "One should be very very careful when mixing patterns,” Wintour said in a Go Ask Anna video. "You need to be very confident and usually pretty tall, otherwise you can look a little busy.”

Diane Kruger is somewhat of a print-mixing expert. The actress regularly attends events and red carpets wearing very precisely crafted multi-pattern looks. Funnily enough, she only stands at the relatively average height of 5’5.”

Shop Diane's Look 

Rule 3: Neon and Fluoro Should be Avoided 

While she has not said it in so many words, it seems Anna Wintour is certainly not a fan of neon colours or fluorescent shades. In a Snapchat video celebrating the US Open, Wintour warned those planning to attend the tennis event, "Don't forget to wear your sunglasses—especially if the male players insist on wearing those ugly fluorescent colours.”

In a separate video, Wintour also told Taylor Swift that "neon leopard-print leggings” were the trend she wished never existed.

Wintour might think fluorescent colours are ugly, but Blake Lively proved wearing the shade favoured by elite tennis players doesn’t have to be. While promoting her film A Simple Favour last year, Lively opted for a head-to-toe neon look from Versace’s spring/summer 2019 menswear collection. Perhaps this suit would make Wintour think twice about her stance?

Shop Blake's Look 

Rule 4: Don't Wear a Boring Sequinned Dress

Much like neon, Wintour hasn’t exactly denounced sequins, though she doesn’t have very positive sentiments about them. When asked about what to wear to a black-tie event, Wintour explained, "Don’t wear a boring sequin dress or a debutante-style dress just because you feel you should.”

In another video, she described the red carpet mainstay of fishtail sequin gowns as something we’ve seen "5000 times.”

While Anna’s critique that a sequinned gown is something we’ve seen a thousand times may be true, there are people who are managing to make sequin gowns feel new again. Zoë Kravitz wore a sequinned gown to Wintour’s annual Met Gala, and let’s just say that it was anything but boring. 

Shop Zoë's Look 

Next, see the winter trends you need to know.