Uh-Oh: Anna Wintour's Boyfriend Owes the IRS a Lot of $$$


(Photo by Getty) Ms. Wintour, why the frowny face?

Shelby Bryan and Anna Wintour at the 2011 US Open (Getty)
Uh-oh, Shelby Bryan — Anna Wintour's longtime man-friend since 1999 — is in a bit of a pickle with the IRS.

According to a report in the Telegraph, the 66-year-old banker-turned-businessman owes the government a lot of dough in back taxes, $1.2 million to be exact. (That's, like, nearly 230 classic quilted Chanel 2.55 handbags, you guys.)

Bryan's whopping debt to Uncle Sam happened after a stock arrangement investors once used to delay paying taxes was "unraveled." And unfortunately for Wintour's beau, the arrangement was banned back in 1997, leaving him to now pay the sum all at once.

A suggestion: maybe Wintour should pull a Kim Kardashian and put her wardrobe up on eBay. You know she's probably got, oh, 20 or so pieces that would add up to a cool mil — we bet she's only worn them once and never will again anyway, right? Nah.

See Anna Wintour's designer-filled lookbook here:
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