Not being the tallest of men, 5ft 7in Lenny may have possibly bought the boots to give him a bit more height. He would not be the first rock star to do so - 5ft 3in singer Prince always wears high heeled boots or shoes.
But if that's not the reason then Lenny may want to consider getting himself to the men's department of Bloomingdale's or Macys very soon.
Or maybe he was just feeling fashionable having been spotted in the front row at a couple of shows during New York Fashion Week including Tommy Hilfiger's show where he was seated next to actress and singer Jennifer Lopez, 42, and Mad Men star Christina Hendricks, 35.
Or maybe he's just been heavily influenced by all the beautiful women he's been with in his life.
Lenny, who lives in his native New York and has been snapped out and about in the city over the last week, has not been short of women in his life.
He famously married The Cosby Show star Lisa Bonet, 42, on her 20th birthday in 1987 after they met two years before backstage at a New Edition concert.
They had a daughter, Zoe Isabella, now 21, but Lisa and Lenny divorced in 1993.
In 2002, he was reported to be engaged to Brazilian model Adriana Lima but he denied the rumours.
In 2003, he met and started to date Nicole Kidman, a couple of years after she and Tom Cruise were divorced.
Nicole and Lenny split in 2004 and Nicole has hinted that they were engaged.
In the September 2007 issue of Vanity Fair, she revealed that she was secretly engaged to someone after her divorce and before she married country singer Keith Urban in 2006, prompting gossip that the mystery man was Lenny.
Fashionista: Lenny watches the Tommy Hilfiger catwalk show at New York Fashion Week next to Jennifer Lopez and Christina Hendricks
Personally I dont have a Love for Wedges So i say Nay to the Wedge but he looks real relaxed and Chill!
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