Anna would never ever wear dainty jewelry I literally wrote that and then laughed when I noticed she’s wearing a tiny chain in the picture above. Anna surprised me multiple times over the course of putting this together. I thought I knew her style to a T. I love her style and strongly identify with her 90’s aesthetic personally. I think of her as timeless, polished, and precise. And when I think of dainty jewelry, I associate it with messy, layered, and boho. Nothing could be further from Anna. But if I stop projecting and push myself into the seat of an objective observer, it’s clear that Anna is wearing that delicate necklace in an exacting way that echoes and complements her spaghetti straps and falls just below her collarbone and just above her dress neckline. It’s not casually or haphazardly layered over her dress. I believe she chose that necklace and every other item she is pictured wearing with great intention and care (and if I’m being honest, I’m feeling compelled to source a dainty chain necklace of my own). When we perceive people in a certain way, there are reasons why. Anna wears a lot of things that don’t seem “Anna” on their own, but when they become a part of her formula, they feel just right. Let’s dive in to the elements that make Anna, Anna.

ICONIC HAIR

Her hair obviously sets the tone for the whole Anna Wintour vibe. She is strong, confident, timeless, considered, elegant but also a bold risk taker. She takes every available opportunity to clearly communicate who she is, beginning with how she cuts and styles her hair. Polished and powerful, not too serious (just yet, this is her 90’s era). A bit softer than how she wears it today. We see more of her face. We see her eyebrows. It’s silkier, has more movement, and the bangs are a bit more fun and choppy. To maintain this level of precision (the length exactly meets / extends her jaw line and the bangs fall just above her eyebrows), my guess is she got at least two haircuts a month (perhaps a weekly trim when she had it blown out). Because of all of the intention behind this look, we instantly perceive her as ridiculously considered, polished, and somehow equal parts severe and lighthearted. It’s one of the greatest hair cuts of all time.

BEADED COLLARS

The occasional dainty chain aside, her signature neckwear cannot be denied. A substantial beaded collar necklace is Anna’s go-to and has been for the better part of five decades. She wears her necklaces at the most flattering place possible: the point on her neck just before it widens into her shoulders, which slims and elongates the neck.

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CREWNECK KNITS

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