skirtedvik

I did a little shopping last week - at white house black market - I had some helpful sales assistance... Tried some skirts and this cowl neck dress in a size 14. It was a little loose at the waist but a belt pulled it in nicely.

http://www.whitehous...=&maxPg=4&size=

With a black or color contrast shirt/blouse under it looked not bad - expecially with a short blazer black blazer. The blazer was a bit small and the dress expensive. But now I know a potential look to do for...

Thanks for the insiration on HHPlace!

Nice dress.

Well, I think it's safe to say I won't be experimenting with faux mammaries anytime soon!

Good decision,male chest - especially if you work out looks amazing in most "women's"tops.

When I first joined HHPlace all those many years ago, I was elated to have discovered like-minded men of all ages like myself who enjoy wearing high heeled shoes. By reading all the many posts by the members here, absorbing their adventures of wearing women's shoes, both in public and in private gave me the courage and the strength to wear heels openly, and that opened a whole new world to me, one I found extremely exciting. In the beginning, I was perfectly content to just wear the shoes, nothing more, but that mindset has clearly changed as an evolution of sorts has taken place.

The bulky block heels I started wearing were replaced by thinner and thinner heels, eventually swapped out for stilettos while I grew into wearing taller heights, when I didn't gove over two inches, today, I'm perfectly comfortable in five inchers, but that wasn't all. After several years of wearing men's clothes with my shoes on my adventures, I began changing, having slowly arrived at the conclusion that such clothes wasn't enough to satisfy me. It began with the bottoms as I replaced men's jeans with women's jeans which looked nicer and sleeker with my heels, and I loved how they looked on me. Next came the tops as I went from men's shirts and sweaters to women's shirts and sweaters, and I was comfortable with that as they also looked nicer on me, and I made the declaration that I would only wear women's clothes on my adventures, and, yes, that included underwear as well and jewelry too.

Finally, the skirts. When I first wore a skirt in public back in the summer of 2008, that proved to be an incredibly exciting and exhilarating experience, and I was effectively hooked. Back then, I only wore skirts infrequently as I still enjoyed jeans, today, I'm wearing skirts almost exclusively as I can't bring myself to wear anything else as all my jeans are in the back of my closet, and I'm in no hurry to bring them back out. On top of that, the shoes, which were once the be all and end all for me has become just one part of my overall image as a freestyler, hell, I've even come to like wearing flats because they're nice shoes to wear with a denim skirt as part of an overall casual weekend outfit. In the past, I thought first about the shoes and what clothes to wear with them, today, I think first about skirts and what shoes to wear with them, that's how much I've evolved, that the shoes come second.

This raises an important question: Does my current philosophy as a fashion freestyler mean I've evolved beyond the tenets of high heel love as exposed here at HHPlace? For me, it's all about the complete head to toe image I present when I go out in public, not just the shoes, and I don't see that mindset changing anytime soon, if at all. I won't deny there are times when I feel more comfortable in a public setting in a skirt than I do in heels, I find that an interesting concept as my evolution has continued. Where will this lead me? Will I leave HHPlace? Nope! I still enjoy being a member and sharing my exploits with others here and reading the opinions of everyone. Nor does this mean I'm not going opt for wigs, fake boobs and makeup, far from it, I'm going to continue wearing the clothes, and shoes that I love----as a man, and that's good enough for me. That's all that I want.

For me, it's all about evolution. Everyone must evolve or perish, and for me, going from just shoes to the joys of free styling has been my evolution, and I can't wait to see where my unique journey will take me next as I continue to grow in my special passion. Opinions?

Apart from fake parts even make-up is ok for a guy.If you present yourself as a guy no matter what you wear you are a freestyler.Nowadays there are marketed for women even the most male/masculine looking items/apparel - and still there are many women who still wear direct male apparel - and unlike us,they have female analog of the item.So why should it be for men otherwise?Our culture made Snowwhite to wear armour/male attire in medieval times (and it is perfectly well accepted) so it is about time things to become equal.

Hi All,

I have been wearing skirts for many years, and I know others here do the same.

For the last 12 months I have worn quite a few dresses as well...

I have even worn mini dresses!

I have learnt what dress styles I think suit me, and styles that work well etc..

I don't think there is much difference between a dress and heels vs a skirt and heels.....

I'm interested in your thoughts?

Is a dress going too far?

I'm not into the false parts/ wigs/ make up etc... but I prefer high heels with lower legs showing, that for me means shorts / skirts and now dresses

I find dresses so easy to wear in the sense that you just jump into a dress, zip it up and go...

They look better than a skirt and top combination

They are so comfortable.

Some pics of me wearing a selection of my favourite dress styles:

(photos are not that good, just quick snaps this afternoon, sorry about that)

far out that took some fiddling around...

I think I'll sit down and have a break!

regards

Heel-Lover

You look great!Your freestyling is impressive and inspiring.You remain a guy and still wearing what you like in a very nice manner.Women have done it centuries ago(wearing the opposite sex apparel,not just trousers,the whole bit),hopefully men will do the same too.

Jeff,you look so natural in these outfits.

I have seen pictures of women from the sixties (of the 20th century) with body hair.Nevertheless they have the freedom without social scorn to dress like a man,so hair removal is possibly avoidable(and they do it).I remove all of my body hair and am a masculine guy in terms of physical appearance(not talking about fashion preferences).

Well, I voted "Man in Heels", but I'm not about to go through all the pages in this thread to find out what I had written originally. No matter, things have obviously changed for me since them as I've fully embraced women's clothing and integrated same into my fashion freestyling. I'm just as comfortable wearing skirts and dresses in public as a man as I am the shoes themselves, in fact, I prefer women's clothing which I find easier to wear and nicer looking as well, just like women's shoes. Is what I and other like minded people here do considered crossdressing? I suppose so, but women do the same damn thing when they wear pants and jeans and flannel shirts and Timberlands, so what's the big deal? In my mind, there is none.

When you present yourself as a man let's use the word freestyler,the cross.... word is very gender biased and leans to men who try to pass and put fake things on.About women you are totally right.

roniheels: The pleasure was all mine!

Jaunt #159, 7/22/2012:

Just a short jaunt today, but it was enjoyable nonetheless as I took the Payless "Jefferson" buckle wedge pumps in brown for a spin, pairing them with a brown polo shirt, a 20 inch tan skirt from JCPenney and my black short strap handbag. In retrospect regarding that outfit, I should have a brown bag to match the shoes, perhaps I'll take that under consideration the next time I'm in a department store. Anyhoo, the brown Jeffersons were just as much a treat to wear as the black pair, stylish, comfortable and damn good looking on my feet. If only I had known long ago how much FUN it is to wear wedge heels! Something tells me I'm going to get a lot of wear out of the Jeffersons in the future.

Back to the outing, I headed westward to Springfield and Office Depot for a fresh ream of paper for my printer, when I entered, most of the sales staff were gathered some fifteen feet away for a meeting on back to school sales and such from what I overheard, a couple of them glanced at me as I walked past, nothing more. At the register with my purchase, I was treated like every other customer (though there weren't many of them at 11:45 on a Sunday morning) despite how I was dressed. After leaving, I walked a hundred yards to Subway for lunch, a couple of motorists driving by glanced at me in passing, other than a dropped jaw, no big deal. In Subway, empty of customers, I had a six inch Italian B.M.T. and a bottle of grape soda and it was a quiet lunch which I enjoyed with today's sport section.

My last stop of the day was to Best Buy as I hadn't been there in a couple of weeks and wanted to see what was new. After parking in the lot and walking towards the store, I did garner a couple of stares as I strolled in, I thought I heard a chuckle, but I wasn't sure, nor did I care. One of the goals of my outings is to be seen and gauge the reactions of those around me, I would say that a good 98 percent of the people in the store paid precious little attention to me. I often find myself idly wondering how many of the people who pass me by take note of what I wear on my little adventures, given how they're so absorbed in their affairs, and whether or not a middle aged black man in a skirt and high heels even registers in their minds. I'm sure I do to some and don't to others. It all depends on the person.

In any event, while short, this was still an enjoyable outing as I got to break in some new shoes and strut my stuff, casually of course. Heh!

Nice outfit and colours,Jeff!

I've been off here for a little while now. Big changes have happened in my life and it's been a very emotional month.

My dad quit his job with a certain German automotive company that he's been with for over 30 years to come and join us doing timber flooring with the intention of me and him starting out on our own doing floors once he has gained enough experience. We'd been put together to only do jobs for the one company but through the company we work for, so we were together all day everyday. Anyway one day driving home from work in the van 'Dude looks like a lady' comes on the radio and he looks at me and starts laughing in a jokey way, which I didn't mind, to me it showed that he's gotten more used to my creativity and has acknowledged me for it.

That night I was in high spirits about my situation and I decided "To hell with it! I'm not hiding it from anybody, anymore!". So I posted a full length picture of me (which you will see at the bottom of this post) up on Facebook for the world and his mate to see. Straight away I was getting lots and lots of positive feedback with alot of my friends saying how proud of me they are for being so open and comfortable about it and that yea it's a shock but they're proud and accepting none the less, alot of these are also male friends saying this by the way! I was feeling so incredibly happy and on a high!

Now you should also know that due to happenings around a month before this, I deleted my dad and his fiance off of my facebook friends list so they could no longer see my posts.

I walked into the living room and I asked my dad if he got the picture I sent to him (i'd sent him another random picture not in any way related to the one I posted on FB). He looked at me and said "I'm more concerned about the picture you've put on FB". I looked at him with a confused face and said "Why? :S" to which he simply replied "Oh fuck off, it's fucking disgusting".

The moment those words came out of his mouth I just forgot everything I was doing and decided that this is it, i'm leaving the house. So I grabbed my 2 suitcases, packed them absolutely crammed full with everything I could, and I stuffed literally everything I own into my tiny little 2 door coupe and made the 10 hour drive all the way from my house in Melbourne to my Girlfriend's place in Sydney (this was at around 11.30pm at night, i'd been up since 6am and worked until 5pm that day also).

I was such a mess, I was in tears that this could have even happened, I went from everybody around me being so kind and accepting and proud of me for who I was, to one of the closest people to me telling me i'm disgusting and completely hating me for who I am. All this happening just day's away from my 22nd Birthday too.

I arrived in Sydney on the morning of Wednesday 4th July at my Girlfriend's place. Booked the hotel that I always stay in (her mother didn't even know about what I wear and still didn't let me stay at their house for some BS reason) and spent the rest of the week and weekend there, 'celebrating' my birthday on the Sunday there with her and her family. My Girl actually bought me a gorgeous pair of pink high heels for my birthday but unfortunately they didn't fit so she exchanged them for a pair of black glittery peep toes which she still has and i'll get them off her when I see her next . I received a text during those few days from my dad apologising for everything and asking me to go back when I was ready. I decided that i'd go back on the Monday, not because I was ready, but because I knew I'd run out of money sometime and would eventually have to go back, so I brought my Girlfriend back with me and we spent the week together down here in Melbourne.

Once back in Melbourne, absolutely nothing was said about what happened between either me and my dad or his fiance. Needless to say the tension in the house was sky high but nobody was game enough to say anything :/ My girlfriend flew home to Sydney last Sunday, and it was only last night that me and my dad finally had a talk about what happened. He said that he still disagreed with me for putting it on facebook, but I simply told him that it wasn't his choice to make, it's mine. I also made a point that telling people individually would make it more of an issue than it really needs to be. I asked him who it was that informed him of me putting the picture up but he would not say, and I asked him if that person also showed him the comments people were leaving and he said that they didn't. So I showed him a few of the comments that people he knows had left, all of them along the lines of "Well done! Fair play! Good on you!" etc.. all he said was "oh okay". I told him that I really couldn't care less what anybody thinks of me, but that I care what he thinks and I ended up in tears again! (what a wuss! ) but it was good, we ended up hugging it out

The tension has now lessened in the house a whole lot after we had that talk last night about it, I think he thinks it's all gone and sorted now, but I can't help still feel a little uneasy, I guess in time i'll get over that though. My dad also said that there is 1 good thing that's come out of this and that it's good that everybody now knows, so he won't be questioned about it for much longer as time goes on, that was the main thing he hated was people asking him about it and he didn't know what to say, but i'd told him time and time again to just be straight with them and even just tell them to come directly to me! but people are snoops and bitches and won't come directly to the source when it's a subject like this I guess...

Anyway that's been my life in heels up until today! Hope everybody else is doing well! To conclude my feelings on this all, I guess all I can say is that IF you are considering being open about who you are and what you wear, make sure you're prepared to go on an emotional roller-coaster and possibly even lose the people you least expect to lose over those you would usually assume would be the ones to say goodbye!

Thanks for reading,

Heelguy

Dress - Cooper St

Shoes - Tony Bianco

You look great,a true freestyler you seem to be.You have my full support and keep posting pictures in various outfits .

I am from Eastern Europe and have NEVER seen a woman having problems for wearing male apparel in public,not even once.

Maybe most males have a judgement that is clouded by the natural attraction to the opposite sex...when I distance myself from that I think that males have their own good looks and we should never fall into stereotypes because on the outside ,the media and etc. bombard us that only women are beautiful and so on...P.S. I am a straight man in a relationship with full acceptance of my battle for gender equality in terms of fashion.

Most women I know (having nice legs) are wearing skirts...

Maybe the fashion is different in larger urban area ?

And your opinion is universal - because you imply that,of course in my humble opinion.Accept that not all people have to agree with you.I accept your opinion without sharing it - that women have better legs and so on.That is highly individual.And as I have always said - compare hens to hens and roosters to roosters.By the way,since women tend to wear even direct men's apparel bcause of social approval - they generally look different than males wearing the same stuff,as a guy in a skirt,top,heels etc.should be compared to other men.

I stopped at a Kroger Pharmacy to pick up a prescription and tried something that was, for me, a little different. I wore a blue suit, black hose, a red turtleneck, and black knee high boots with 2” block heels. These are the same boots I wear at work under slacks.

I got a couple glances as I walked in from the parking lot. In the store there was a long line at the pharmacy and I had to just stand there for at least 10 minutes. When I waked up to the counter the gal that waited on me (young black) was clearly uncomfortable with the way I looked. I didn’t push the issue and only spoke enough to complete the transaction.

I was comfortable in the outfit but I did miss my thigh boots and heels. I’ve mention before that wearin them gives me the mental license to wear anything else. The outfit today was much more mainstream except that a guy was wearing it.

Thanks alll for the comments on the last outfit.

Nice outfit and cool jacket - looks better than drab man's clothes.You are a brave man,sir!

The simple answer is because most mainstream men's clothing over time has become largely gender neutral for many of the reasons touched on here. But not all men's clothes are so. When one sees a woman in a clearly male suit, tie, shoes and pants, for example, it stands out as a statement of fashion boldness, if still falling short of radical. But it gets notice and sets the brain at work as to the motivation behind it.

I've seen many women in NOT the female version of male clothes and shoes and even some in formal male attire(though most wear usually man's t-shirts,trousers and shoes) and still it goes rather unnoticed and non life threatening as a man in a dress/skirt & top and heels would be on the street.My sister does that and noone is questioning her normality (she wears sometimes non formal male apparel and has 2 kids).

All fashion that is masculine is socially accepted to women,not just shoes and noone si going to give away equality for free.Most men and probably most women would be against gender equality in fashion - men because of the macho bull*it ideology and women because of reason number one and the fact that to wear the opposite's sex stuff and so on is an advantage while you keep your things only for yourself.

skirtedvik: Don't worry about it. No harm. no foul.

Thanks Jeff,I have always enjoyed your posts,pictures and the fact that you wear what you wear as a guy.

Fake stuff? Huh? Where did THAT come from? Admittedly, I do dabble with a waist cincher every now and then to hold in my tummy depending on what I'm wearing, but that's all.

Dww: Ahh, but that's the beauty of that pic. Anybody can wear pants, but it takes tremendous cojones for a guy to wear a skirt in public, and look dynamic as he did!

English is not my native language - so what I meant is that similar to you I do not put fake parts!Probably I wrote it a bit dubious.Sorry about that.

Last time I knew there was nothing fake about JeffB.

I corrected my statment as it is truly unclear,as I said I am not a native English speaker.I wear "female"tops without fake parts,so does Jeff- that is what I intended to write.

1.Skirtedvik: Perhaps that blazer was the best he could manage with that outfit. I've seen women wear long blazers, so it's not an uncommon look. Like roniheels, I too would give him plenty of compliments, judging from his bold stride, he just oozes confidence about himself and the way he chooses to dress. Awesome!

2.By the by, skirtedvik, what sort of neckline would you suggest I try?

On the first one:Still,not my cup of tee - if it is long better be tailored,not the typical formless male fashion.

On the second:As a Fellow freestyler I would wear something like this ,but black for those skirt and heels - remeber I do not put fake parts in the same manner as you do!

Thanks though I am not a father yet.

I'm loving the look! That tan number is gorgeous and shows off your legs so well! You'd have killer pins for a pencil skirt if you were to push the envelope that bit more.... having had a dig down the back of the internet, I see a few guys in London are already trying skirts as an alternative to the usual same old trousers

I just love this guy's confidence, plus the skirt looks great

Looking forward to the next jaunt

The "man's" jacket seems inappropriate to me.If it was short tailored jacket better results for sure.

TBG: Many thanks for the kind words. I'm glad to have provided inspiration to you in your own adventures as you inspired me in mine! After all, I never would've tried my hand at thigh high boots if I hadn't read your exploits!

roniheels: Thanks for the compliment. Much obliged! By the by, it just so happens that I'm in the process of putting together an outfit that promises to be even more "summery" for a future jaunt. And speaking of jaunts....

Jaunt #155, 6/17/2012:

Just a short outing as I had a couple of chores to take care of, but that doesn't mean I can't turn it into an adventure, even if it's a small one as I went out in a black polo shirt, my 20 inch tan skirt, the Payless "Kailey" pumps in black patent and my trusty black handbag. My first stop of the day, having gone out to the western 'burbs was to Office Depot to buy a new toner cartridge for my home printer, the heels of the Kailey pumps made a delightfully solid click as I walked towards the store, and seeing my reflection made me smile because I looked good in my outfit. Once inside, I was helped by one of the salespeople who treated me professionally like any other shopper as he directed me to what I needed and went to the register where a pretty black girl in her late 20's looked me up and down and gave me a smile before ringing me up then wishing me a happy day. Cool.

My second and final stop of the day was to Best Buy as I needed to replace the charger I use to juice up the rechargeable AA batteries I use in my camera. The parking lot was nearly full and people were coming and going, and I took notice of all the females who came and went, and, taking into account the outfit I wore (which you can see below), I found myself for about the umpteenth time wondering if I had overdressed for the ocassion, while most women I saw walking in and out of the store sported t-shirts, tank tops, shorts, sweatpants and the ever omnipresent (and despicable) flip-flops, there I was in a skirt and heels, and feeling perhaps just a tad out of place. And while I've fought over this "problem" in my mind many times before, I've come to accept that if I'm going to wear women's clothes and shoes in public, I know that I have to dress up a tad more than the average female because of the image I'm presenting to the world at large, so, with a shrug, I hopped out and went in the store.

Just as I thought, the store was pretty busy for an early Sunday afternoon, and I did attract a fair amount of stares here and there, nothing I hadn't experienced before, however, no one made a big deal of how I was dressed. Progress I suppose. Of course, I can't just pick up what I need and get out, no-ooooooooooo, I had to spend little over half an hour gazing at all sorts of gadgets and gizmos before I finally pulled away from it all (though reluctantly) and went to the register with what I needed. A short outing, but enjoyable like all my other adventures.

Nice outfit.Maybe try a more open top,with other type of neckline.

SleekHeels: Thanks for the suggestions. I found them useful and I'll try to utilize them. Wearing dresses and skirts is clearly a sign to me that it's no longer about just the shoes, rather, the entire outfit, and, at the risk of sounding vain, I love showing off my legs, something I can't do properly in jeans. Heh! As for confidence, as long as you have it, and flaunt it, it doesn't matter what the season might be, just go out there and do it!

Jaunt #152, 5/26/2012

Even though the forecast called for steamy, summer like temperatures, it would also be sunny, good enough conditions for a Saturday jaunt as I took my new Payless "Cori" flats for a second trip while wearing a blue campshirt, a new skirt I bought from Sears and a handbag. Given how most women dress down on weekends, I decided to follow their example, for the most part. Heh! I was especially eager to wear the new flats again as they were very comfortable, stylish and, yes, cute! And what self-respecting freestyler wouldn't want to wear cute shoes? As for the new skirt, it's a gauzy, black, 30 inch A-line with a matching half-slip like attachment beneath, and, like the shoes, it proved to be a lot of fun to wear. My first stop was to Starbucks to read a magazine, buy a cool beverage, and be seen. Even though there was quite a crowd in the place, no one paid me any attention as I got my order, sat in a chair and spent over thirty minutes there.

After that, it was off to center city and my favorite comic shop, as usual, finding a place to park proved time consuming and I wound up in a spot over a block away, no prob, again, it offered me a chance to be seen in my outfit, and, other than a trio of young black males who broke out laughing as they drove past, no one paid me any mind as I strolled to the shop, enjoying the soft swish of the skirt about my legs and the comfort of the shoes. I spent nearly half an hour in the comic shop, half that time yakking with the staff about The Avengers which I had seen last weekend and loved, as usual, they ignored what I wore. Then I left the store, walked up the block to a convenience store to play the lottery and buy a newspaper, then it was off to South Jersey. When I entered the Chick-Fil-A near Moorestown Mall, I did get some glances from a few people here and there, but nothing more than that, I bought my order, ate while gazing through the sports section and left, simple as that.

My last stop of the day was the nearby Barnes & Noble where I spent another half-hour plus in the dining area with a couple of magazines and a tall iced tea. Yes, I drank a lot, but it was hot, and it's important to stay hydrated. There wasn't much of a crowd in the store, and what people there were in attendance ignored me. Funny how a guy in a skirt didn't raise so much as one eyebrow. Nevertheless, I had another fun time freestyling, it felt great to wear that breezy, gauzy skirt, and those "Cori" flats were an absolute delight to wear because they were so comfortable! Who needs heels when I've got great flats like those! I can see I'll be getting a lot of use out of those shoes in the weeks to come!

Nice skirt!

Thank you.

It was just a basic top shirt, nothing special.

It would be better if it is not the basic boring men's shirt .

You look great!Maybe try a short tailored jacket instead.

I hadn't been out in my heels and dressed up for SOOOO long and I decided that last night I would go out with one of my gay friends to a place called BAR362 in St Kilda. I hadn't been there before so was quite excited to be finally going out again and going somewhere new I wore my purple Steve Madden heels with the sparkly bow on the back, a short almost suit-like skirt from Supre, a purple singlet from Witchery and a gold bangle also from Supre. My girlfriend helped me choose this outfit too!

I made the drive into St Kilda which is around 40 minutes from my house as I live out in the Suburbs. I parked my car around the corner and met my friend out the front. There was a small crowd of maybe 10-15 people outside the club also, and the whole 50 yard walk up to the club I think every single one of them was staring at me! LOL it was quite nerve racking, but once I got up to the group and went over to my friend and said hello, alot of the people came over to talk to me and were very inquisitive, but very friendly also.

We stood outside talking for around 10-15mins and then went inside. As more people saw me, more people would come over and ask about me, it was quite funny to see the confusion of telling a group of gay guys that even dressed the way I was, I am a straight male haha, my friend was loving seeing people baffled by me, but they were all extremely polite and nice

That's pretty much how the rest of the night went too, I spoke with a few of the Drag performers that were on that night and they all said I looked amazing and were very nice which was good! We left at 1am as that's what time the place closed as it's Easter. All in all I very much enjoyed my night there and hope to be out and about in my heels alot more often than I have been (here's to hoping anyway!)

A picture for you all to see what I was wearing...

Heelguy

Great freestyiling!Compliments and that is how I understand gender equality!

Now if he wears the same garments while feeling manly, then he only is doing what women have done with pants for decades : choose by themselves.

I am a freestyler so I am doing just that.No fake parts and names and etc while wearing whatever apparel I like.