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Anna Wintour on Fashion: Embrace Individuality, Confidence, and Timeless Style

Anna Wintour

 

Anna Wintour is seen outside Burberry during London’s 2019 Fashion Week. Anna Wintour, the editor-in-chief of Vogue magazine and artistic director of Condé Nast Publications, cuts a commanding and authoritative figure wherever she goes. And as the most powerful woman in fashion, she is scrutinized head to toe, her word is taken as gospel and she is revered within the industry.

Her influence extends beyond the silky confines of the fashion world, having raised millions for pet projects like the annual Met Gala, the highly anticipated  fundraiser for the Metropolitan Museum of Art’s Costume Institute with a coveted guest list. So what does the most powerful woman in fashion wear?

Despite a rumoured yearly clothing allowance paid by Vogue and a job that advocates buying the latest and trendiest things, she surprisingly sticks to a signature style  one best described as feminine and classic. So to mark Wintour’s 71st birthday on Nov. 3, we’re revisiting some of the fashion icon’s most legendary looks and gleaning lessons we can incorporate into our own personal style.

NEW YORK, NY - MAY 02: Anna Wintour attends the "Manus x Machina: Fashion in an Age of Technology" press preview at the Metropolitan Museum of Art on May 2, 2016 in New York City. (Photo by D Dipasupil/FilmMagic)
Despite the notion that fashion pros love to wear black, the editor is almost always seen wearing colour and loves bold patterns. Here she doubles up on prints and wears a striking dress with an overcoat in contrasting colours. The lesson here is not to be afraid of big, bold prints. The flowers on this dress might be extra large, but they are a simplified design executed in wonderful pastels. Cinching it with a belt helps define the waistline and ensures Wintour doesn’t get lost in the oversized patterns.
NEW YORK, NY - APRIL 13: Conde Nast Artistic Director Anna Wintour, shoe detail, attends the world premiere of "First Monday in May" during the 2016 Tribeca Film Festival at John Zuccotti Theater at BMCC Tribeca Performing Arts Center on April 13, 2016 in New York City. (Photo by Taylor Hill/Getty Images)

Fashion magazines like Vogue usually obsess about shoes, detailing the latest, the greatest and the must-have footwear of the season. Surprisingly, editor-in-chief Anna Wintour sticks to a classic slingback with a medium heel by Manolo Blahnik for daytime, which works with every outfit. For chilly days, her go-to footwear is knee-high boots. Heel heights and styles may come and go, but you’ll never find her in a wedge or a ridiculously tall stiletto. The trick to making one style of shoe work with your entire wardrobe is to keep it simple, demure and in a neutral colour.

 

NEW YORK, NY - APRIL 13: Conde Nast Artistic Director Anna Wintour attends the world premiere of "First Monday in May" during the 2016 Tribeca Film Festival at John Zuccotti Theater at BMCC Tribeca Performing Arts Center on April 13, 2016 in New York City. (Photo by Taylor Hill/Getty Images)

Sunglasses are a booming business for designers since most people buy more than one in a variety of styles. The editor is famous for hers — dark, oversized and in a classic rectangular shape — and  is rarely seen without them. Find the perfect frame to suit your face, free of embellishment and large logos, and you really only need to own one pair.

 

attends the Carolina Herrera Fall 2016 fashion show during New York Fashion Week on February 15, 2016 in New York City.

Wintour found the perfect hairstyle to suit her face years ago and has stuck to it since  a bob with sharp bangs. The biggest change the famous bob has undergone over the years is that it has lightened in colour. Most hairdressers will suggest you change your hairstyle as you get older,  as your face changes or the mood strikes for something different, but a simple, classic cut never goes out of style.

 

PARIS, FRANCE - MARCH 07: Anna Wintour is seen arriving at Stella McCartney fashion show during Paris Fashion Week : Womenswear Fall Winter 2016/2017 on March 7, 2016 in Paris, France. (Photo by Jacopo Raule/GC Images)

The one part of her wardrobe that Wintour tends to make a loud fashion statement with are her coats. She tends to favour classic animal prints, bold prints or, in this case, a beautiful floral embroidery. However, the shapes are still simple with classic cuts. The lesson here is that a great coat can hide a multitude of sins. It’s the first part of an outfit one notices, so invest in a spectacular piece. After all, winter is a dreary time of year and your image  and your spirits  need a boost.

A sure sign of a powerful woman? She doesn’t tote a handbag. That’s just one of the perks of having a chauffeur and car service to store mundane things such as keys, credit card and purses. However, the one thing Wintour always has on hand is her phone.
As much as she is known as the editor of Vogue, Wintour is the mastermind behind the annual Met Gala, the celebrity-studded fundraiser where the worlds of fashion, sports and entertainment merge. The event is one of the most exclusive invites and the red-carpet fashion is the ultimate in peacocking as celebrities try to outdo each other by dressing to a Costume Institute exhibition theme. But the haute hostess of fashion sticks to her own signature Gala look  usually a couture gown by Chanel in a straight-line silhouette. When it comes to hemlines, this floor-length look is one of two Wintour wears. For daytime, she favours a midi-length dress or skirt suit, and she never wears a pantsuit to the office.

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