Have a look at this article from the NYT in regards to men in heels. Certainly interesting, possibly inspiring.
Via New York Times:
On a recent summer evening at Mr. Black, a dance party held every Tuesday at Bardot on North Vine Street, Sean Wagner was towering above the crowd. Mr. Wagner, 23, is tall even in socks (6-foot-2), but that night he had some extra help.
On his size 11 feet were a pair of eight-inch bright neon green lace-up stiletto ankle boots, procured from The Ladies Studio Exotic Shoes on Hollywood Boulevard.
He jokingly dubbed them “my usual hiking shoes.”
Mr. Wagner was otherwise dressed in men’s clothing: a loose-fitting black tank top with a pair of tapered black pants. He had a neatly trimmed beard, and a pair of black-framed glasses sat perched on his nose.
“I never leave the house with less than eight inches on my feet,” he said cheerfully. “It helps you see over the cattle.”
Mr. Wagner was not the only man wearing high heels (but no other women’s clothing) that night. At Mr. Black, Luke Nero, a promoter, estimated that 10 or more men were traversing the dance floor in a pair of pumps. “I went to a loft party yesterday, and there was a guy in normal shorts, normal tank and really hot red pumps. That’s it!” he said. “Everyone was like, ‘Oh my God, I love those shoes!’ ”
In a way, Mr. Wagner and his stiletto-wearing cohorts are repeating history. Until Napoleon banned them, high heels were considered a sign of nobility in France during the 18th century and were favored by men as well as women; long before Louboutin, Louis XVI donned five-inch red-accented heels depicting wartime battle scenes.
In 2009 the Atlanta hairstylist Derek J became famous after appearing on “The Real Housewives of Atlanta” wearing women’s pumps with jeans and a sweater, the same year that the designer Rad Hourani sent male models down the runway in boot heels reminiscent of Prince and ’70s glam rockers like David Bowie and David Johansen of the New York Dolls.
At Mr. Black, two best friends, Coy Barton, 24, and Mark Cramer, 25, who go out together as a duo dubbed Coma, were dressed alike in buttoned-up white shirts, dark gray dress slacks pegged at the ankle — and black leather ankle boots with peep toes that showed off their black painted toenails. “I’m in Steve Madden, he’s in Chinese Laundry,” said Mr. Barton of their shoes, “These were $115. Mine were, like, $170.”
Expensive, yes, but nothing compared with the price of Gregory Alexander’s prized pair of Balenciaga six-inch wooden wedges: $2,000. They were safely ensconced in his closet. That evening, Mr. Alexander, 26 and a host at Mr. Black, had paired Yves Saint Laurent’s Imperiale platform stiletto ankle boot (original retail price: $1,395) with a leather motorcycle jacket, tight black jeans, a white shirt and a skinny black tie. “They were a pretty penny,” said Mr. Alexander, 26, referring to the YSL’s. “They were a Valentine’s present to myself. I had them engrave a card for me, too.”
Mr. Alexander, who runs a popular party called A Club Called Rhonda, said he owns about 30 pairs of women’s heels. He wears a women’s size 11, and just barely fits in most designer shoes.
Mr. Wagner, meanwhile, said he often resorts to paying for custom-made heels for his larger feet.
“I love the height,” he said. “It helps when you’re in a club. I’ve bought Louis Vuitton. I’ve bought Gucci. But a lot of designers don’t go high enough for me. I found a company in Arizona that will do 15-inch heels for $3,000.”
Jeff Paice, a clothing designer at Mr. Black who had dressed up his buttoned-up black shirt and black pants with a pair of sandal wedges, said he was bored with the usual choices. “There’s nothing for guys,” he said.
Mr. Barton agreed: “I literally look at girls and think, you have so many options. You have jumpers, you have skirts, you have dresses, you have pants, you have shorts. Boys have pants and shorts. Or suits and a shirt.”
None of the men interviewed considered themselves to be in drag. “I always make it very clear that I am a man, and I’m not trying to portray an illusion to anybody,” Mr. Wagner said.
Though some would call it a form of drag, he added, “As far as we’re concerned, this is just bringing a look to a club — which is what you are supposed to do.”
“I wish society was more acceptable of men wearing heels,” Mr. Paice said. “I think it’s fun. I think it makes a statement.”
Mr. Alexander cited reasons for wearing high heels many women have known since they were invented: “It’s a power thing. You’re higher than everybody else. You make more sound. You walk a different way. It makes your legs look better.”
He added: “I don’t ever take them off. I even drive in them — stick shift.”
Last summer, he broke his ankle trying to jump a fence to get into a party while wearing a pair of heels. “I was in a cast for four months,” he said. “They told me I should never wear heels again, obviously.”
“But I don’t know,” Mr. Alexander added, admiring his YSL-clad feet. “I’m back.”