The celebrity circuit is teeming with male stars who have taken that long walk across the screen in gender bending footwear.
Patrick Swayze, Wesley Snipes and John Leguizamo perhaps made the most convincing and memorable men in heels as three drag queens stranded in small town America, but they were by no means the first.
There were a few earlier instances, but the real jumping off point was Some Like it Hot in 1959, which starred a flamboyant Jack Lemmon next to a more reluctant Tony Curtis in drag, high-heels and all.
Lemmon stole the show from Marilyn Monroe with his natural attitude and flair as a musician in women's shoes and clothing on the run from gangsters.
Tom Hank starred opposite Peter Scolari in the TV series Bosom Buddies in 1980, as two men who opt to dress in drag and pose as women to secure an apartment.
Dustin Hoffman made movie history as a man in heels when he starred in Tootsie in 1982, as a man who dresses as a woman to get a better job and ends up taking it a bit too far.
That year also saw the incomparable John Lithgow as the ex-football transsexual in The World According to Garp opposite the legendary Robin Williams.
Williams took his own turn in drag as Mrs Doubtfire in 1993 sporting ghastly women's shoes.
This was followed in turn by the famous To Wong Foo, Thanks for Everything, Julie Newmar in 1995.
1998 saw undeniably masculine and utterly convincing Anthony Tyler Quinn (Boy Meets World, Melrose Place) sporting killer heels and silk stockings in the TV version of Tootsie, a series called Ask Harriet.
Many of these actors have gone on to become A-list celebrities, and a common thread is how very masculine many of these men are.
Hanks was anything but effeminate in Castaway, and Snipes played the baddest boy on the block in Blade.
Swayze was rarely cast as anything other than a beefcake, but handled the various types of ladies' footwear in To Wong Foo with grace and aplomb - no doubt thanks to his dance career.
Matthew Broderick and country singer Garth Brooks among others have done skits for late night comedy shows such as Saturday Night Live, and there are numerous other actors who have proven they can strut in women's shoes as well as the women themselves.
Woody Harrelson played a transvestite lady of the night in Anger Management - with clogs as footwear and a startling Dutch accent.
Other countries have their share of cross-dressing stars as well.
Britain's Monty Python and their Canadian counterparts Kids in the Hall have performed many skits in drag.
Eddie Izzard, the well known British comedian and actor has been a hit on the comedy circuit for over a decade.
His trademark black leather thigh-high boots with stiletto heels have become legendary as well as his ability to manage them as he dashes back and forth across the stage.
Do girls really have more fun? Catch a few of these men in heels, and decide for yourself!