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Anna Wintour: The Holy Grail of Fashion

Even those people who are not fashion conscious know how Anna Wintour looks. Being the epitome of fashion expertise, she is surely the most famous person in the world when it comes to style. She is the editor-in-chief of Vogue US, and she does what she is best at. Although she is always seen incorporating key trends in her outfits (like various prints for example) she stays loyal to her everlasting style, with the recognizable short bang bob, and evergreen silhouettes. Always topping worldwide best dressed lists, she still isn’t letting down her game when being 66! Read about Meeting Women Over 50 with Fabulous Style.

Earlier in her career she had been known for mixing and matching t-shirt with designer labels, but as she grew older, she swapped those with famous Chanel jackets and skirts, worn with the sole purpose to evoke her chic self. Also, the perfect addition to her short hair are the Ray-Ban Wayfarers, allowing her to keep reactions private (great idea Anna, but it is known that she also wears them due to vision problems). Anyway, let’s get to admire her outfits!


Anna is seen in her classic favorite silhouette that is never above the knee, and she nailed it with this trench coat, that has a classic tailoring with a beautiful abstract print to it that adds a modern touch to spice up the coat.

Two-piece suit

Anna Wintour before MaxMara show during Milan Fashion Week Day 2, street style on February 26, 2015 in Milan.

Ah, the classic Chanel suit. So effortlessly worn by Anna, it would make even Coco jealous at her elegance! Although this is not a classic black and white model, this is also a perfect example how Anna loves adding a bit of edginess to classy things, like it is shown in this slightly sequined Chanel suit.

Anna Wintour poses for photographers before Tod’s fashion show, Milan Fashion Week Day 3 street style on February 26, 2016 in Milan

A little splash of color

Anna certainly enjoys a little splash of color (and we do too!)! Add a subtle 70s flair to your outfit by wearing a bright, warm color with a printed neck scarf, paired with a tailored camel coat of course! More Elegant Fall Fashion for Women Over 50 can be found here.

Print dress

Again, this is a perfect example of how to wear a grasshopper-worthy print with ease in your sixties. Bravo Anna!

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