This Christmas is the Countess of Wessex’s 20th Christmas as a member of the British Royal Family. Over the past two decades, she has worn a fascinatingly diverse array of hats to church on Christmas Day at Sandringham:
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Green felt top hat with raised pleated brim in 1999; Ecru folded brimless hat with black curled quills in 2000
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Camel split crown felt cloche with bow in 2001; Prim navy domed pillbox with burgundy feathers in 2002
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Chocolate felt wide-brimmed Philip Treacy sidesweep with leaf trim in 2003; Repeat of the camel felt cloche in 2004
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Black felt sidesweep with feather flower in 2005; Burgundy humped crown cloche in 2006. Both by Philip Treacy.
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Textured straw beret in 2008; Red felt beaded flower headpiece in 2009. Both by Rachel Trevor Morgan
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Purple button percher with jewel trimmed ruffle in 2010; Navy beaded felt pillbox in 2011. Both by Jane Taylor
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Chocolate felt cut leaf headpiece in 2012; Beaded black button percher with flying bow in 2013;
Leopard print felt pillbox with flat black bow in 2014. All by Jane Taylor
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Grey felt percher with jinsin twistl in 2015. Black laser-cut percher with raw-edge crin in 2016. Both by Jane Taylor
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Navy felt leaf headpiece in 2017; Black crushed velvet percher with birdcage veil in 2018. Both by Jane Taylor
UPDATE- Since this post was published, the Countess has worn the following hats on Christmas Day:

Maroon velvet veiled bandeau by Jane Taylor in 2019
This mix includes extremes from classic to unconventional, restrained to exaggerated, familiar to experimental. I can’t say I’d choose many of these hats for myself but I find myself drawn in to many of them for a closer look- they are fascinating! It’s this bravery, versatility and unpredictability that makes Sophie’s millinery so much fun to follow. What hats here stand out most to you?
Photos from Chris Jackson, Chris Jackson via Getty; Splash News/Corbis; Tim Rooke/REX/Shutterstock; Pool/Samir Hussein/Wirestock via Getty; Getty as indicated