"I'm not a chicken. I'm just really hesitant." -Frasier Crane
Question #11137 posted on 12/06/2004 4:21 a.m.

Dear 100 Hour Board,
Will high heels ever come back into style for men?
- teetertotter

A: Dear teetertotter,

Good question. Let's look at the history of high heels, for those who are thinking, "'Come back' into style for men? When were they ever in style for men?"
Approx. 4000 B.C.
Earliest depictions of shoes (flexible leather pieces held in place with lacings) in ancient Egyptian murals on tombs and temples.

Approx. 200 B.C.
Platform sandals called kothorni, with high wood or cork soles, become popular among Roman tragic actors.

King Henry II of England popularizes shoes with narrow, pointed toes. Legend says they hid his deformed toes.

Knights of Richard the Lionhearted begin to wear sollerets, downward-curving pointed toes, to keep their feet from slipping out of stirrups.

A law passed in Paris bans university professors from wearing shoes with long, pointed toes. However, shoe toes, a symbol of rank, grow longer and pointier during the next two centuries, culminating by about 1382 in the spiky-toed cracowe. Kings and princes sometimes wore toes 30 inches long.

Knights fighting in the Battle of Sempach in Switzerland are forced to amputate their shoes' long toes after dismounting before they can advance on foot.

Approx. 1500
Shoes begin to be made in two pieces, with a flexible upper attached to a heavier, stiffer sole. This leads to the introduction of the heel, devised as a better way of keeping a rider's foot in the stirrup. Heeled boots for men quickly become fashionable.

Henry VIII of England favors wide-toed shoes, sometimes 12 inches across, which had to be stuffed to keep them on his feet.

Short-statured Italian bride Catherine d'Medici, married at 14 to the Duke of Orleans, wears shoes with two-inch heels to exaggerate her height. The high heel may have been invented by Leonardo da Vinci (1452-1519).

Mary Tudor ("Bloody Mary"), another vertically challenged monarch, wears heels as high as possible. From this period until the early 19th century, high heels are frequently in vogue for both sexes.

An extreme shoe style called chopines, popular among women in Italy, Spain and France, had pedestals of cork or wood as tall as 24 inches. A Venetian lady wearing chopines needed two servants to help her in and out of a gondola.

Pilgrims arrive in the Massachusetts Bay Colony. A law is passed prohibiting "excess in bootes."

French shoemaker Nicholas Lestage, so clever at his trade that some accuse him of sorcery, becomes shoemaker to Louis XIV. The heels of Louis's shoes, some decorated with miniature battle scenes, are as tall as five inches. High "Louis" heels are also fashionable for ladies.

Madame de Pompadour, tiny-footed favorite of Louis XV, popularizes high, narrow "Pompadour" heels. Ladies tape their feet to reduce their apparent size and faint at court.

Marie Antoinette ascends the scaffold to be executed wearing two-inch heels. However, in the wake of the French Revolution heels become lower than at any time in the 18th century.

Early 1800s
Flat shoes and Grecian-style sandals become popular.

Approx. 1865
The "sneaker" or plimsoll, a canvas-topped, rubber-soled shoe, is invented for badminton and tennis. Ladies' heel heights vary but stay below two inches during the rest of the century.

The ladies' "pump" or court shoe, a British invention, reaches America. Shoe stores begin to stock shoes with a range of widths around now.

Approx. 1955
Tall "stiletto" heels for women's shoes, invented in Italy, become a fashion rage. Very pointed toes come into vogue for both sexes.

Return of the platform shoe.

Modified source from http://users.powernet.co.uk/wingett/History1.htm
So, there we have it: men used to wear high heels. As we all know, fashion history usually repeats itself ("those who do not know history are condemned to repeat it"), so you should not be surprised to hear that some men are trying to bring high heels back into style. Which brings me to my next question: Are you one of those men? Are you or someone you know looking to make the switch? If so, have I got some advice for you!.

A Primer on Heels at Work

1) Gauge the atmosphere at your place of employment. Is the dress code flexible or stringent? Observe what female co-workers wear. You don't have to copy what women wear, you only want to get ideas.

2) Start out slow. No four inch stilletos on the first day out. Ease your way in with one or two inchers. Gauge how well that goes over that goes with co-workers.

3) Wear black. This is just my opinion mind you, but since 99% of men wear black shoes, your chances of acceptance is greater in this color than anything lighter in shade.

4) Coordinate your clothing. Don't dress like a slob, even if you're not in heels. Go with tasteful dress shirts and tailored slacks. In my opinion, you can never go wrong in that kind of ensemble.

5) No spike heels....PERIOD! Again, this is just me, but I don't think spikes just don't look good with slacks, opt for thicker heels.

6) While on that subject, don't be prejudiced against block heels. They're good to wear because the width provdes more stability when walking or standing.

7) Set limits on heel heights. My rule of thumb is nothing over three inches. You don't want to call unnecessary attention to yourself, especially in a serious work environment.

8) If possible, look for heels with squared toes. This style is not only roomier and more comfortable for day to day wear than the traditional pointed toe variety, their mannish appearance will aid in acceptance. Case in point: when I first wore a pair of three inch block heeled loafers with squared toes, co-workers actually thought those were MEN'S shoes!

9) Don't be extravagant with flashy colors or outrageous styles like strappy sandals, mules or stilletos. Remember, you're in a work environment, and that sort of thing just wouldn't go over very well.

10) Be calm, don't be nervous when wearing your heels for the first time at work. If you act as if it's no big deal, then you won't draw attention to yourself and make people wonder what's wrong with you.

11) Be prepared for a variety of opinions from co-workers when they see your heels. While I've had nothing but compliments (even good natured kidding about my added height), my case is unique. There's no way to know if you'll be accepted in your workplace. That's why you should start out with a low height.

12) Respect your co-workers. Don't force others to look at your shoes. No one else does that, why should you? If someone asks about your shoes however, then you can show them off, but do so with pride, never be ashamed about what you choose to wear.

From http://freespace.virgin.net/firey.fox/jeffb.htm

The *real* question is, when will skirts for men come back into style? After all, you shouldn't have to cover your nice heels up with slacks all the time--show some skin! Give us a little leg! These men are totally behind you:
100 Men in NYC Seek Right to Wear Skirts
The Atlanta Journal-Constitution (02-08-2004)
NEW YORK (AP)--About 100 men in minis, midis and even tutus took to the streets of Manhattan to call for an end to the tyranny of trousers.

"We're not transvestites, homosexuals or cross-dressers," David Johnson told the New York Times for Sunday editions. "We don't want you to call us Jean or Sally. We're men. Men who want the right to wear a skirt."

Johnson, a retired teacher from Poughkeepsie, N.Y., and the other pants opposers walked several blocks from the Guggenheim Museum to the Metropolitan Museum of Art, where they visited an exhibit called "Bravehearts: Men in Skirts." Their presence attracted confused looks from a few fellow visitors.

Ingemar Johnsson, 39, came from Sweden to join the march Saturday. He told the Times that men in Europe often wore skirts and pantaloons until the time of the French Revolution, when pants became the expected masculine attire. Others pointed out that Scottish men have donned kilts for centuries.

"The male bird is always the pretty one, not the female," another participant, 27-year-old Chris Taylor, told the Times. "Why can't the male human being dress with style and color?"
Interested in wearing a skirt? Can you picture yourself in one of these?

From http://menintime.de

Here's a testimonial and advice from a guy who is all about wearing a sarong:
"You are the sexiest thing I have seen today," said somebody else's woman, staring a hole through the front of my gray and black sarong. "How would you know?" I responded. "It's still early."

When I was in high school and becoming image-conscious, I asked my father if it was true that clothes make the man. "You're a man on two feet," he said, disgusted, rolling his eyes a bit. "Man makes the man." Back then I wore WilliWear, by black designer Willie Smith - I had an eye for classic style, even back then. I got laughed at because of my allegiance to his brand, but I wore his fine suits and separates by the season - well ahead of the curve, well ahead of my time. Twenty-odd years later, fashion sheep will be loyal to any tag with a name on it, but I am still the urban style iconoclast. This summer, I'm rocking a sarong almost exclusively.

It was the fall-winter of 2000 when I first thought seriously about sporting a wrap. I was going to see D'Angelo and I wanted to sport a different look. See, just like in your town, dudes be wearing any type of Sunday suit hook-ups or technicolor ensemble to the spot, and I had to separate myself from the suckas. Besides, I'm ashamed to say that I don't own a suit that fits, and those wack fake Versace shirts aren't my flow - my style is a little more subtle than that. So, naturally, a sarong seemed like a logical alternative to consider.

I wore it to the concert and caught snickers from the derby and doo-rag crowd. None of them had heart enough to say anything stupid - after all, I'm kind of a big guy. I saw one of my dudes at the spot and he ran up to me, mouth agape. "That is just the phatest s--t," he said. "I wish I was man enough to play a wrap - are the sisters checkin' for it?" Were they ever. My girl really dug the look on me, and so did everybody else's girl - all eyes and wet thighs whenever I passed by. Afterwards I retired the wrap, just breaking it out occasionally. But I vowed I would find a way to play that style every day, if I could.

This summer, I decided I was gonna wear wraps in place of shorts -shorts make my boys sweaty and give me heat rash - and with the heat in the 90s on the regular, this seemed like the time to set it off. So most days nowadays, you'll find me on the streets of Cleveland, downtown no less, in a skirt. To be honest, there is little to no reaction in my hometown - nobody even blinks. I don't know if it's because I'm a somewhat well known writer here, and people assume anybody who writes for a living must be crazy anyway. Or maybe between the two feet of hair and the floor-length sarong, their circuits are just completely overloaded: Too Black, Too Strong. Whatever the reason, I walk the streets unmolested, save for the women who stop midstride and fall out of car windows trying to check my steez. "You are the sexiest thing I have seen today," said somebody else's woman, staring a hole through the front of my gray and black wrap. "How would you know?" I responded. "It's still early." What can I say? Chicks dig the skirt. I even wear it to work. Dats right - and I work for the white man, just like you.

I'm employed by a major not-for-profit company, and there is nothing in the dress code that says I can't wear a sarong to work. The first time, there were second looks and a strange inquiry ("What do you have up under your skirt?" asked one of my female coworkers. My response? "How badly do you want to know?"). But my bosses are mellow - they accept my wrap as an extension of my Afrocentricity, and that bodes well for their progressive thinking and commitment to diversity.

The wrap has come to symbolize my refusal to be reconstructed by whatever people's assumptions are. It's also the ultimate assertion of manhood for me: it speaks to my roots, my warrior status, my fearless nature in a way that fake dashikis don't. I mean, it's like there's an "S" on my chest or something - I have never felt more masculine, not ever, than when I don the wrap. Why? Well, maybe because it is so not a question of sexual preference or identity. I don't have any gay friends with balls enough to wear a sarong. Besides, it's unisex, stupid - if all it takes to make you question your sexual identity is a garment, you've got more questions than I can answer, RuPaul.

See, the thing about wearing a sarong is that, as a man, you have to have a certain confidence, a certain arrogance. You must be absolutely secure in your manhood - flat out - or it won't come off well. You'll look like a man in a skirt: clumsy, misplaced and utterly ridiculous. In a wrap, whatever where-with-all you have as a man is up for scrutiny: you've created an artificial vulnerability that requires strength to secure. Plainly speaking, a man in a sarong projects an audacity and demands a respect that khakis don't. Fact is, you might not be man enough to pull it off. If you think you're ready, I got a few tips for you. Finding a wrap is more than a notion - it's not like Laura Ashley makes a men's skirt line. The trick for me was to find something masculine - a tough skirt, if you will. I couldn't find what I was looking for at first, and the cultural shops in my town wanted too much bread for some of the stuff they had. So I improvised: I went to my local head shop and got a few of those groovy, thin cotton throw-rug joints for 20 clams each.

Choose earth tones when picking out a wrap. Browns, blacks, greens, burnt oranges and yellows are preferable - bright colors denote femininity. Only traditional or tribal patterns - no tie-dyes or flowers, Nancy. Wear fitted T-shirts or short-sleeved shirts on top: let them guns blaze. Footwear is player's choice - blunted toes for winter and sandals for the summertime look best. If you hot like that, take a bold leap and play a three-button jacket with an open flare-collar shirt. Mudcloth is an okay material for winter, but roll with a light to heavy cotton in the hotter months. Wear linen pants up under in the wintertime; in the summer, anything goes.

So here I am, on the street of Cleveland, Ohio, in a sarong. Rollin' hard, Jack. I go out of town and sport it, and cats ask if I'm from overseas or something. But I know there are a few cats on either coast wrappin' on the regular. Fashion comes and goes, but style is timeless. And here I am: well ahead of the curve, well ahead of my time. I'm pretty sure this style won't catch on, but maybe it should. Dad was right: clothes don't make the man. A man can stand on two feet - sarong and all.
Source: www.africana.com/Utilities/Content.html?&../cgi-bin/banner.pl?banner=Lifestyle&../Column/bl_voices_63.htm

You can find a lot more information out there on skirts for men, including http://www.kiltmen.com/

And if you're going to show off those legs, you're going to want to start wearing nylons come winter. I found these tips and success stories for men who want to start wearing pantyhose:
If you want to have beautiful pantyhosed legs, you must shave your legs. It is particularly true for Asians because their hair is usually dark. In the past my sheer pantyhose covered my dark haired legs, which is not so nice. With the legs shaved, they look smooth and sexy!

Also, Wear a pair of 2.5 or higher high-heels! You legs will absolutely look longer and slimmer. Do more exercise for your legs! Recently I have followed the "Claudia Schiffer - Perfectly Fit Legs" video tapes , and her other productions. The exercises are really nice ones!

If you feel embrarrased to buy 'ladies' things, just pretend that you are buying for your wife/girlfriend.

We played pool a lot at a local pub and are always making silly bets on the side. So... I bet her if I won, she would have to wear pantyhose to bed. She thought for a second and asked what she got if she won. I thought for a second (yea right) and told her I would wear them if I loss too. Of course I loss. She ended up like it very much and the next time we were both wearing and have been for about 4 years now. I've told others about this and it's proved useful. Any game the same.

On my wife's birthday, I bought her a 'ladies' shaver as a birthday gift. After sending her the gift, I secretly shaved my legs. Later on I let her see and said that I tried to use the shaver to see if it was comfortable. Of course, it didn't matter. The fact was that I had my legs shaved - very beautiful after shaving! I also received a gift - she complimented my legs in sheer pantyhose!

[To avoid runs] Before you put the pantyhose on, apply some lotion to your hands. I have been able to make my hose last a very long time by doing this. This advice is for men and women alike. Also, when they start to sag, do the same thing and it will make it easier to pull them up...with you palms that is, don't use your finger tips...
Lastly, to wrap up the whole heels-skirt-hose ensamble, you probably need a purse. You can now buy men's purses bags here: http://www.manbag.com/product.htm

- Piquant
A: Dear Piquant:

You just wrote eight pages, four of them on skirts, and didn't once mention a lava lava. My Polynesian friends are going to be ticked.

-- Misaneroth
A: Dear Misaneroth:

I guess you missed the story about the guy who wears a sarong, which according to my research on Google is often the same thing as a lava lava.

- Piquant