Wintour isn’t anti crop, but she’s extremely pro-proportion. If you’re baring midriff, the rest of your look better be sophisticated and definitely not paired with low-rise anything.

Summer’s not an excuse to become a walking billboard. Subtlety reigns. A discreet designer detail? Acceptable. Monogrammed from head to toe? Absolutely not.

Wearing head-to-toe neon is like shouting in someone’s face. A pop of lime in a clean silhouette? Approved. A blinding yellow romper? You’re on thin ice.

Oversized bug eyes, bedazzled frames, or novelty shapes? Hard pass. Think sleek, timeless, face-flattering shapes that add mystery, not costume vibes.

If your sandals look like they were crocheted, glued together, or designed for camping, they’re probably not Anna approved. Go for strappy, sculptural, or minimal, always chic.

Wearing head to toe black might feel safe and slimming, but Anna Wintour sees it as a missed opportunity. Summer is about light, movement, and color. Swap the funeral core for crisp whites, saturated pastels, or bold hues. Monochrome black in July? That’s not chic, that’s heatstroke.

Cover ups, sarongs, and bikinis masquerading as tops have no place in the city. Wintour draws a firm line between resort wear and real wear.

That shell necklace you’ve been wearing since college. Time to retire it. Anna sees accessories as the punctuation of an outfit; if it doesn’t elevate, it eliminates.

In Wintour’s world, hats are not statement pieces; they’re subtle punctuation marks. Because they sit so close to the face, she believes they should frame, not distract. Think clean lines, minimal detailing, and nothing that screams for attention. Overly embellished, theatrical hats? Too costume, too loud.

Summer is short, but that doesn’t mean your outfit rotation should be. Wearing the same linen dress on loop says, “I gave up,” not “I’m iconic.”

Following Wintour’s summer rules isn’t about being elitist; it’s about being intentional. Your closet should serve your style, not enslave it to trends or comfort alone. So, if you’re feeling personally attacked by these laws, take it as a sign: it might be time to elevate your summer game. Not for her but for yourself. Because in Anna Wintour’s world, style never takes a vacation. And neither should yours.

Disclaimer: This list is solely the author’s opinion based on research and publicly available information.

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This is where I share the good stuff: beauty drops, fashion finds, travel moments, and confidence notes from my heart to yours. .