Share your best Freestyle Fashion pictures here.

[Maximilian]

what do you think?

I hope you had a nice evening at the dance club

If you chickened out that time my solution is this...a few shots of a nice single malt scotch for that "liquid courage" feeling and off you go. Don't forget to take a cab or have a buddy drive though

[HappyFeat]

A wonderful look all the way around. I love the color of the shirt.

[JeffB]

what do you think?

Impressive! Very impressive!

[Dawn HH]

Looks good to me. Cheers--- Dawn HH

[kneehighs]

heeluis--not to stir up any fire or anything, but I'm surprised you're not wearing some Helmut Lang skinny leather pants. You look great though!

[Maximilian]

Returning from Japan after 3 weeks, seeing great heels and styles in Japan and not being able to wear my heels there, gave me a big urge to wear them once I got back home.

I feel as though my confidence to wear more feminine styles in public has gone up. I've done the skirt/high heels thing in public already, although not very often yet am now coming to terms with the fact that I simply love that look on me. In my humble opinion, a skirt and heels are a killer combo. I like that look even more than boots over skinny jeans or tights.

I was looking for a tunic to purchase for a while that can pass on as a long sweater. During my search I came across a black short dress by Alfani that looks like a tunic and loved it. In the past I refrained from the idea of wearing a shorter skirt or heaven forbid any sort of dress as I felt like that was really going into "cross dressing" territory.

However, after thinking a lot about it I came to the conclusion that I should wear what I like regardless and boost my carefree feelings about other peoples opinion about my fashion choices.

Lets be honest here, as long as people don’t talk to you or here your side of the story, they’ll think that I crossdress anyway just by wearing low block heels. They’ll think that I’m gay as well. I had no problem with that perception while wearing stilettos in public so why think otherwise while wearing a dress as a guy. So, it seems yet again that I'm the one that's putting boundries on my fashion desires. I always liked the shot skirt look on me but was concerned of that image in public. It took a while to get over the concern to wear a knee length skirt as well.

I'm at a point now that I want and will wear skirts more in public since I'm more comfortable wearing it and simply love the skirt/boot combo.

I've also started to build my confidence to wear that Alfani black dress in public since I just love how it feels and looks on me.

My standard operating procedure is to venture out first at night to build confidence.

My style of choice for that night (I was out between 4:00-6:00 am Monday) was:

1- Alfani leather jacket

2 - Alfani black short dress

3 - black leggings

4 - Giuseppe Zanotti black leather knee high 4" stiletto boots

Here are the photos of my look (I apologize for not taking photos outside since it was night time and my camera doesn't take good photos at night, even with the flash. I wish I could though):

My first stop was a very large power center with many outlets. At night it is virtually empty. I like going there at night for a first time public outing because it is lit quite well so while walking I see myself, I go there alot during the day so being there already dressed like I am helps boost my confidence, my heels on the sidewalk make very nice clicking sounds especially these stiletto boots and also because I can see my reflection clearly on the store windows which is a treat.

I didn't run into anyone at that hour. The only traffic were the garbage trucks. It was raining slightly but not heavily so I didn't get really wet. The only problem with wearing a skirt/dress are the lack of pockets so I had to get a bag. The bag isn't very feminine but the shoulder strap is thin and makes it look like a womans bag. Personally, I don't like carrying bags/purses but there aren’t many options if there aren’t any pockets.

It was fun, yet after a while it was kinda boring.

I decided to venture to places that in the past I was too scared of going there in public in heels especially with a skirt. My first stop was Whyte ave, the main entertainment area of Edmonton where many bars and trendy boutiques are located. Since it was around 4:30 am, everything was closed and there were barely any people there. I parked my vehicle and went for a walk. I was nervous because of the other "weirdos" I encountered, especially while passing them. Now that I think of it, it might not have been a good idea to wear those clothes in that part of town by myself at night since I could've been mugged but nothing happened. By the end of my walk I was very happy and went back to my vehicle.

My next stop was downtown Edmonton. During the day there are many people around, most of them dressed in business attire. I was dressed pretty classy and would fit in perfectly during the day hours if I were a woman. It was already after 5:00 and the bus service started operating. There weren't many people in the street yet but traffic increased. I walked to the entrance of a club I've wanted to go to in heels for a long time since they have an alternative dressing night on Saturdays and I was wondering what the closest parking area would be. I walked around the downtown core for a few blocks, nervous yet increasingly happy by seeing my reflection on the store windows and listening to the clicking of my boots. I passed a few people who took a quick glance yet said nothing and continued on their way. It was very early in the morning and I doubt they were awake enough to even contemplate what they had just witnessed hehe.

By the time I got back to my vehicle I was tired from walking but felt like I was on cloud 9. Before going home I drove to the park and sat on a bench next to the pond. Walking with stilettos on the grass was a strange yet comfortable feeling compared to walking on concrete.

I got home at about sunrise and said to myself that I have just about reached my ultimate level of feminine fashion I like with only one hurdle left, wearing the same outfit during the day or during the evening with lots of people around.

It was a great night. I can't wait to be back in town and try it out as well as increasing my skirt/heel outings as well.

[Maximilian]

2 more pics

[kneehighs]

I actually like the collar on that dress and it seems like you can never go wrong with a leather jacket. Nice one!

[spiker]

Wow! Nice one....seems like you should start your own thread now! Now to think of a verb that starts with M! Keep us posted on your experiences - at least that way those of us that don't have your confidence can relive your experiences... Spiker. (The outfit looks great by the way)

[Elegant]

I've always been keen on your accounts. Great look and attitude, as always. Have you thought about contributing to http://highheelspassion.blogspot.com ?

[JeffB]

Wow! Nice one....seems like you should start your own thread now!

I couldn't agree more! Max, you SHOULD start your own thread! I am so impressed with your sense of style it's not funny! You look sensational in your latest pics! That dress and boots combo was absolutely killer! Bravo to you, my friend!

[Mr. X]

As Darth Vader Would say. Impressive, most impressive. Well done Max!

[dingpat]

As Darth Vader Would say. Impressive, most impressive. Well done Max!

What an amazing nerd moment! love it!

[WhyNotMenToo]

Hello Max,

You said "Lets be honest here, as long as people don’t talk to you or here your side of the story, they’ll think that I crossdress anyway just by wearing low block heels. They’ll think that I’m gay as well. I had no problem with that perception while wearing stilettos in public so why think otherwise while wearing a dress as a guy. So, it seems yet again that I'm the one that's putting boundries on my fashion desires. I always liked the shot skirt look on me but was concerned of that image in public. It took a while to get over the concern to wear a knee length skirt as well" Well I like the way you think, I'd like to envite you and any one that feels the same as Max, I found a yahoo group the skirtman that is pushing Equality in Fashions http://groups.yahoo.com/group/Skirtman/ I hope I have not broken any rules here but I think the more people push for fashions freedom for men the better and I think the owner and Moderator can use a little help too.

[WhyNotMenToo]

Max, This is a great look!!!

[heeluis]

Wow, Heelius.

What a great looking ensemble. Totally a fashionable 'guy in heels' look. This shot really strikes me as a very passable, fun, aggressive and 'I'm cool with myself' look. If you're on the street in this look, the heads turning should be thinking 'heels for guys look great'. Any other shots like this would really be appreciated as they easily provide justification 'to wear heels as a guy fashion.' Can you tell us about the evening out...or is that in another thread that I've missed?

SP

Hi Spartan, I was only out arround the corner to have a beer or two and this is funny because I was walking down the street and suddenly a guy atared at me from a bar through the window and I was allready chicken out as I thoght -Oh, I know him from somewhere-

Well he finally came out and even though it took a minute for both of us to remember who the other was, we finally found out that we new each other over friends in common and a girl with whom I used to work with. Anyway we had a great chat and suddenly he said- Hey what great shoes are you wearing! Respect! So it was everything fine and I came back home happy!

[Maximilian]

For those of you who have been following my posts and personal journey of gradually wearing in public all the fashion styles I like, know by now that high heel shoes/boots are only an accessory to a total look I'm interested in, a look regarded by society as feminine/crossdressing yet by me...a badass/confidence booster look. I've always been a big boot fan. I ride horses and riding boots have always been fun to wear. A good quality riding boot worn over a pair of breeches does wonders to a womans look (one of the reasons I started riding many years ago). When I wear my breeches and boots (they are Cavallo boots, a high quality german brand) I always get a ton of compliments so I guess women like that look on men. Lucky for me, English style riding is considered a womans sport in Western Canada. Male riders are rare and guys think that only gay men ride, another stupid stereotype yet very beneficial for a guy like me who is surrounded by women with no competition. However, the problem with good quality real leather riding boots is that they are designed for riding. They need to be stiff fo protection purposes as well as competitions where you are judged by your appearence. Dressage boots are by far the most elegant since that riding sport is all about elegance. Heaven forbid they'll slouch. So wearing real riding boots as fashion boots is very uncomfortable and makes you walk like a robot. I've been looking for fashion riding boots for quite some time. Since I have enough black boots, I wanted a different color. I've always liked cognac colored boots. Yesterday I've received my latest purchase, a pair of "Pour la Victoire" brand letaher cognac knee high/otk boots with a 1 inch heel. The boot type is "Malorie". Basically, they look like tall riding fashion boots, a very popular style with the ladies these days...and myself heheh. They also make very nice clicking sounds since the heel is made of wood. I took them out for a test run today. I'm still quite self aware of my look when wearing tall boots over skinny jeans, flats or high heeled boots. It's simply one of those looks that scream for attention. With the boots I wore a pair of Levis blue skinny jeans, a striped dress shirt and a brown leather belt. I really liked how I looked and the boots were exactly what I was looking for. First stop was Future shop (electronics store like Best Buy). I had to buy a few things and wondered around the store (which was pretty empty) for a good 20 minutes. I spoke to 2 young salesmen, a guy and a girl in their early 20's. The girl didn't seem to even notice the boots and pointed me to the right direction. The guy however, although he didn't say anything specific with regard to my look, did seem to take special interest in me. He was very helpful and nice. He asked me if I had been to the store before. I told him that I've been there many times and he said that he never saw me. It seemed like he was one step away from asking for my phone number. Luckily, he didn't. Before leaving the store I had to stop by at a counter to get a bag for my purchases. The girl there examined me while I walked towards her. She was very polite. Just before leaving she said "I like your boots". I thanked her and went on my way. My next stop was Walmart. I spent about 15 minutes in there walking around yet didn't notice any stares or double takes. I left Walmart and drove to my local Safeway. 10 minutes, and a few stares later I was on my way home. That concluded my first outing in my new boots, a regular outing for me. This is how I looked like:

[Mr. X]

Way to go Max! The pictures and outfit look great even though they are not my particular style.

[Guest]

your high stylin as usual Max, LOVE your new boots!!!!

[roniheels]

Here is a few pics I took at work. Feelin a little frisky

pic 1

pic 2

pic 3

pic 4

pic 5

Pretty high heels. Nicely done. Thank you!

[danielp6406]

Here is a few pics I took at work. Feelin a little frisky

Nice heels you got there mrhiheelz :-) May I ask you what type of work you are doing ?

I guess your co-workers and boss are very open minded. Congrats

...Yesterday I've received my latest purchase, a pair of "Pour la Victoire" brand letaher cognac knee high/otk boots....

Very nice boots indeed. I also like "riding style" boots but not OTK.

I got one pair which I like very much but they are not "real" riding boots like yours

(See picture below except mine are black). I hope you like your new boots as much as I like mine !

[WhyNotMenToo]

For those of you who have been following my posts and personal journey of gradually wearing in public all the fashion styles I like, know by now that high heel shoes/boots are only an accessory to a total look I'm interested in, a look regarded by society as feminine/crossdressing yet by me...a badass/confidence booster look.

I've always been a big boot fan. I ride horses and riding boots have always been fun to wear. A good quality riding boot worn over a pair of breeches does wonders to a womans look (one of the reasons I started riding many years ago). When I wear my breeches and boots (they are Cavallo boots, a high quality german brand) I always get a ton of compliments so I guess women like that look on men. Lucky for me, English style riding is considered a womans sport in Western Canada. Male riders are rare and guys think that only gay men ride, another stupid stereotype yet very beneficial for a guy like me who is surrounded by women with no competition.

However, the problem with good quality real leather riding boots is that they are designed for riding. They need to be stiff fo protection purposes as well as competitions where you are judged by your appearence. Dressage boots are by far the most elegant since that riding sport is all about elegance. Heaven forbid they'll slouch. So wearing real riding boots as fashion boots is very uncomfortable and makes you walk like a robot.

I've been looking for fashion riding boots for quite some time. Since I have enough black boots, I wanted a different color. I've always liked cognac colored boots.

Yesterday I've received my latest purchase, a pair of "Pour la Victoire" brand letaher cognac knee high/otk boots with a 1 inch heel. The boot type is "Malorie". Basically, they look like tall riding fashion boots, a very popular style with the ladies these days...and myself heheh. They also make very nice clicking sounds since the heel is made of wood.

I took them out for a test run today. I'm still quite self aware of my look when wearing tall boots over skinny jeans, flats or high heeled boots. It's simply one of those looks that scream for attention. With the boots I wore a pair of Levis blue skinny jeans, a striped dress shirt and a brown leather belt. I really liked how I looked and the boots were exactly what I was looking for.

First stop was Future shop (electronics store like Best Buy). I had to buy a few things and wondered around the store (which was pretty empty) for a good 20 minutes. I spoke to 2 young salesmen, a guy and a girl in their early 20's. The girl didn't seem to even notice the boots and pointed me to the right direction.

The guy however, although he didn't say anything specific with regard to my look, did seem to take special interest in me. He was very helpful and nice. He asked me if I had been to the store before. I told him that I've been there many times and he said that he never saw me. It seemed like he was one step away from asking for my phone number. Luckily, he didn't.

Before leaving the store I had to stop by at a counter to get a bag for my purchases. The girl there examined me while I walked towards her. She was very polite. Just before leaving she said "I like your boots". I thanked her and went on my way.

My next stop was Walmart. I spent about 15 minutes in there walking around yet didn't notice any stares or double takes. I left Walmart and drove to my local Safeway. 10 minutes, and a few stares later I was on my way home.

That concluded my first outing in my new boots, a regular outing for me.

This is how I looked like:

Max,

How can I get this boots like the ones you are wearing and what was the price?

[WhyNotMenToo]

For those of you who have been following my posts and personal journey of gradually wearing in public all the fashion styles I like, know by now that high heel shoes/boots are only an accessory to a total look I'm interested in, a look regarded by society as feminine/crossdressing yet by me...a badass/confidence booster look.

I've always been a big boot fan. I ride horses and riding boots have always been fun to wear. A good quality riding boot worn over a pair of breeches does wonders to a womans look (one of the reasons I started riding many years ago). When I wear my breeches and boots (they are Cavallo boots, a high quality german brand) I always get a ton of compliments so I guess women like that look on men. Lucky for me, English style riding is considered a womans sport in Western Canada. Male riders are rare and guys think that only gay men ride, another stupid stereotype yet very beneficial for a guy like me who is surrounded by women with no competition.

However, the problem with good quality real leather riding boots is that they are designed for riding. They need to be stiff fo protection purposes as well as competitions where you are judged by your appearence. Dressage boots are by far the most elegant since that riding sport is all about elegance. Heaven forbid they'll slouch. So wearing real riding boots as fashion boots is very uncomfortable and makes you walk like a robot.

I've been looking for fashion riding boots for quite some time. Since I have enough black boots, I wanted a different color. I've always liked cognac colored boots.

Yesterday I've received my latest purchase, a pair of "Pour la Victoire" brand letaher cognac knee high/otk boots with a 1 inch heel. The boot type is "Malorie". Basically, they look like tall riding fashion boots, a very popular style with the ladies these days...and myself heheh. They also make very nice clicking sounds since the heel is made of wood.

I took them out for a test run today. I'm still quite self aware of my look when wearing tall boots over skinny jeans, flats or high heeled boots. It's simply one of those looks that scream for attention. With the boots I wore a pair of Levis blue skinny jeans, a striped dress shirt and a brown leather belt. I really liked how I looked and the boots were exactly what I was looking for.

First stop was Future shop (electronics store like Best Buy). I had to buy a few things and wondered around the store (which was pretty empty) for a good 20 minutes. I spoke to 2 young salesmen, a guy and a girl in their early 20's. The girl didn't seem to even notice the boots and pointed me to the right direction.

The guy however, although he didn't say anything specific with regard to my look, did seem to take special interest in me. He was very helpful and nice. He asked me if I had been to the store before. I told him that I've been there many times and he said that he never saw me. It seemed like he was one step away from asking for my phone number. Luckily, he didn't.

Before leaving the store I had to stop by at a counter to get a bag for my purchases. The girl there examined me while I walked towards her. She was very polite. Just before leaving she said "I like your boots". I thanked her and went on my way.

My next stop was Walmart. I spent about 15 minutes in there walking around yet didn't notice any stares or double takes. I left Walmart and drove to my local Safeway. 10 minutes, and a few stares later I was on my way home.

That concluded my first outing in my new boots, a regular outing for me.

This is how I looked like:

Max, how can I get the boots?

[Maximilian]

Run a search on Ebay/Google/Shopstyle for: "Pour La Victoire Malorie boots" I got mine on Ebay for almost 200 usd. These boots were a smash hit this season and are hard to find now. The largest size I've seen for these boots is a womans size 10. These boots come in black, cognac and grey color.

[onlyboots]

hi,i bought these knee-high brown boots on ebay,no zip ,heel 4"...i love them...i wore the same outfit on the street last night...it was very very funny:w00t2:...what do you think?

[Jimnj3]

I think they look great. What type of responce did you get out in the street?

[danielp6406]

...I wore the same outfit on the street last night...it was very very funny:w00t2:...what do you think?

Very nice boots. Also curious to know what type of reaction you got on the street.

[Bubba136]

What was so "very, very funny" about the experience? The laughter at your look from others or the feeling you had while wearing them?

[Maximilian]

Here is an update of my outings during the last few days:

On Thursday, my agenda was a trip to the movieplex with my brother. My brother is fully aware of my style and doesn’t even notice it anymore or at least he pretends not to notice. He doesn’t care, that’s what matters.

I was in a bold mood. The outfit of choice was highly noticeable, not much the outfit but more the boots I wore:

- Alfani black leather jacket

- Nygard Brown turtleneck sweater

- Tan colored belt

- Blue skinny jeans

- Vicini OTK brown boots with 3 inch heel.

As with previous outings in these boots, I got a LOT of impersonal attention. These boots would be big attention grabbers if worn by a woman so imagine what they do when a guy wears them. It was a beautiful sunny day and there was no way in hell I could hide my footwear. I didn’t want to either.

Staring at me began when walking from my car to the movieplex. When I got to the ticket purchase line, there weren’t that many people but I did wait 5 minutes in line because of lengthy conversations with the tickets person. Standing in line is usually THE place to get noticed, especially if you wear stiletto heel OTK boots which were completely visible.

The reactions though were predictable and quite funny for me. My fav reaction is when someone notices it and fights a losing battle to try not to laugh/smile and dare not look at my direction to try and not offend me (you’d figure they’d understand that a guy who has the balls to go out in such an outfit wouldn’t be phased by childish giggles). To me it’s funny because I know exactly why they are laughing and I myself try not to laugh. It happened to this teen girl in front of the line. She was smiling and trying to compose herself. Her girlfriend though didn’t seem to even notice yet I’m sure she did as well as the other 20 people in line.

Most though seemed to look and then pretend that nothing is out of the ordinary, no grins, smiles or eye contact. A group of kids who were about to walk out of the movieplex were smiling to themselves while checking me out. They all try to turn away when I stare at them with a smile.

I counted 4 double takes, one very noticeable one while leaving the movieplex and walking back to my car. I passed a guy in his late 20s/early 30’s who didn’t seem to notice me when I passed him. However, I decided to look back and there he was, looking at me and smiling. I smiled back and continued to my car.

I got no attention in the theatre itself since it was dark because the movie started just as I walking in. Try grabbing a seat when it’s dark and walking in heels.

Before going to the movie, I thought about going to a restaurant after that but changed my mind since I wanted to try and cook a dish that I’ve eaten in Japan.

All in all, it was a good outing with predictable reactions of people to such a high profile style.

[Maximilian]

On Friday, I went to a local mall as well as the supermarket. The outfit of choice was:

- Brown pleather jacket

- Striped dress shirt

- Tan leather belt

- Tommy Hilfiger white skinny jeans

- Pour la Victoire cognac leather otk riding boots with 1 inch heel.

I basically looked like a polo player going to the mall after the game.

I’ve spent a good 2 hours at the mall, walking around with hardly any reactions. Of course there were stares but people stare at you all the time no matter what you’re wearing.

The most obvious reaction happened when I entered a clothes store and asked about a leather jacket. The 2 salespeople, a young man and young woman clearly noticed my outfit. They didn’t laugh but had that pre-laugh/grin on their face and were quiet when I was browsing the store (they were talking when I just came in). Since I was the only customer at the time, I’m sure they took interest in me. They were polite and friendly when I asked a question though.

They weren’t the only people I asked questions. I was trying on jackets/coats in the women’s dept. of The Bay as well as Sears. Many women passed by and were browsing right next to me while I was standing in front of the mirror trying various jackets that would look good with my outfit. The mirror was right next to the main strolling area of the stores so MANY people saw me. I asked the saleswomen if there were other sizes for jackets that I liked and they were completely professional with no sign whatsoever of amusement or discomfort.

With regard to the supermarket there is hardly anything to mention since there were no unusual encounters. It’s a huge outlet supermarket with many people coming and going. I’ve been there while wearing heels/skirts/tall boots over skinny jeans many times and never had any problems.

All in all, another uneventful day in freestyle wear. Then again, most days are.