'The September Issue' Rewatch: Anna Wintour, Grace Coddington, and the Sienna Miller Hair Crisis (with Kate Casey)
Montag, 31. August 2026 · 1 h 12
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The September Issue is R.J. Cutler's 2009 documentary about the biggest issue of Vogue ever made up to that point — 843 pages, 13 million copies sold.
Amy is joined by Kate Casey, host of Reality Life with Kate Casey and a documentary and reality TV expert, to rewatch it seventeen years later. They get into what Anna Wintour really thought of the film, why she and her Vogue team hated Sienna Miller's hair so much, how it all aged, and much more.
CHAPTERS
Introduction
13 million copies sold — and what's left now
How Anna and Grace actually met
The retailers' breakfast, when Vogue set the trends
"Your girls always look the same" - Anna at her harshest
Anna at home, and the kids who didn't follow her
The Sienna Miller cover disaster
843 pages, and the era that ended
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Follow Kate Casey
🎙️ Reality Life with Kate Casey:
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Spotify: open.spotify.com/show/7iZzKUbEWAsWVkFRebb9Gu
📷 Follow Kate on Instagram: @katecaseyca
This episode was edited by Chrissi Harris.
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