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