The 20 Best Anna Wintour Outfits That You Probably Haven't Seen Until Now

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Anna Wintour's style file has been carefully documented over the last 40 years. Since becoming head editrix of American Vogue in 1988, the now-mogul has layered up (fur coats, high-neck frocks and tall boots) and down (slinky sequin dresses and strap-y heels) for just about every occasion. Though known for her consistency, it may come as a surprise that the best Anna Wintour outfits are actually super different from one decade to the next. Her now-polarizing aesthetic has changed significantly since her early years, which sported all the exuberance of a young editor in the heyday of her career.

The early '90s, for example, were laden with youthful silhouettes including leggings and crewnecks, mesh cut-out tops and coogi skirt-suits, which made what followed all the more surprising. Her signature style as we know it — colorful, printed frocks, flanked by shadowy Chanel frames and criss-crossed Manolo Blahnik's (which are remade from a mold of her foot every season) — was solidified much later. As is true in fashion and life, it's all about the journey; and Wintour's is no exception.

Ahead, you'll find a sequential round-up of AW's very best ensembles, from Met Gala red (or, sometimes pink) carpets to far-flung fashion weeks over the years. Be sure to shop similar standout pieces, to ensure your style is just as timeless.

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