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Anna Wintour’s Signature Look: Iconic or Overrated?

The untouchable style of Anna Wintour: why does no one question it? The style of the Great and Terrible Anna from the perspective of an independent stylist.

The anniversary of the most influential woman in the world of fashion Anna Wintour, has just passed by with a bang. I’ve read countless laudatory articles and still can’t understand why no one asks the obvious question that keeps me awake at night: Why is the woman who dictates fashion trends worldwide and heads the most influential magazine on fashion and style – Vogue – herself not in vogue?

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Let’s look at Anna impartially, from a stylist’s perspective, and acknowledge – such hairstyles are no longer worn! Yes, her iconic bob is already outdated! But how can that be, you ask? Because bobs are supposed to be timeless?

Indeed, but it’s all about proportions and details. Anna’s bob, in terms of proportions and trends, has “frozen” in the mid-90s – a teased bob from all sides with baroque volume is outdated, not to mention the ends that are curled inward and the thick medium-length fringe…

For comparison, here’s what seems like the same bob with bangs but is actually current and modern – honey blonde instead of yellow blonde, a longer bang, an asymmetrical parting instead of a straight one, and of course, no volume at all – it has been outdated for 20 years. The devil in fashion is always in the details. Do you think we should give Anna the phone number of Taylor Swift’s hairstylist?

There are also questions about her sunglasses. They are the simplest way to instantly become trendy. The frame shape that Anna has worn for the past 20 years is now outdated, and let’s be honest – it doesn’t really looks good.

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In the last five years, fashion has seen a boom in sunglasses – there have been thousands of new shapes, styles, and rhythms, with old forms returning but updated – in different finishes, frames, and proportions.

But the biggest questions are raised by her style. How can someone who has access to the latest novelties in fashion and style wear such outfits?

Let’s examine several of Anna’s looks from a stylistic, trendy, and up-to-date perspective.

Outfit 1

For example, this blue polka-dotted dress.

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Seriously? A blue dress with large polka dots, an A-line skirt, and a low waistline paired with pink pearls and boots in the style of the ’90s? But let’s think – maybe she wears it because it’s looking cool? No, again! Not too large facial features and suddenly a plum-sized print on the dress.

Okay, but maybe this is just a one-off failure? We all occasionally choose outfits for going out that aren’t very successful. 

Outfit 2

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Let’s look at the next outfit with a black dress and jacket. What could go wrong? The jacket! Let’s examine this half-circle neckline, fitted waist, absence of buttons, and blurred stripe print. I won’t even mention the unfortunate sleeve length that makes the arms look as unflattering as possible.

Outfit 3

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Anna Wintour loves large floral prints, let’s forgive her this small weakness, but if flowers are large and pink, it is an inevitable fashion disaster. But that’s not all! Just consider her outfit – huge pink flowers on a white dress (already doesn’t sound great, right?), but all this is combined with a bag of outdated shape in brown-beige tones, and as footwear, cream espadrilles with daisies. And the final touch – solid black sunglasses!

I would change everything, but even this dress can be “saved” with a white, bright pink – matching the flower edging on the dress, or green bag – contrasting with the flowers, even a black bag would look better and match the dress. And another important rule – cream with white is best not to wear, so any white shoes would look much more successful. 

Outfit 4

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Besides the clothing itself, there are also questions regarding the combinations. Why did she wear a plaid fringed scarf with a floral print dress? It seems as though the scarf didn’t quite fit into her wardrobe, so she had to settle for wearing it around her neck.

Outfit 5

Who do you think is the fashion editor here, and who isn’t? Surely not the woman in the green dress with pink flowers? But no! Phan Dang Hoang – the stylish man in a fashion shirt and pants – stands out unfavorably when compared to Vogue’s chief editor’s style.

Hey! She’s 75 years old and can’t keep up with the ever-changing trends from TikTok! – you might say. Yes, but let’s remember that Anna isn’t selling potatoes at a supermarket; she leads the most influential fashion project in the world! And there are many fashion bloggers her age who look incredibly cool at 70, 75, and even 80 years old! Think of Lynn Slater, Linda Rodin, or Carmen Dell’ Orefice – how stylish, relevant, and always on-trend these women are, despite none of them heading a fashion magazine!

Let’s wish Anna good health, for her to get a pixie cut (or at least schedule an appointment with Taylor Swift’s hairstylist), switch to larger and more trendy glasses, and update her wardrobe – fewer floral dresses and more contemporary pieces like jeans, faux fur coats, leather skirts and trousers. This way, the title of “the first face of world fashion” demands being stylish and current!

What do you think about Anna’s style?

author avatar
Ekaterina Savitskaya
Award-winning stylist and founder of the Paris School of Style with over 20 years of fashion industry experience. Worked with top brands such as Cosmopolitan, L’Etoile, Bosco Di Ciliegi, Vivienne Sabó and others.

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