To Dress, or To Overdress?

[JeffB]

Here’s a question worth pondering: is being overdressed a bad thing? When I embraced the unique lifestyle of the fashion freestyler, I made it a point to always, and I mean ALWAYS look my very best. I mean, if I was going to traipse out in public wearing women’s clothes AS A MAN, then I’d damn well better make sure I didn’t look foolish or inappropriate. Because of that particular mindset, I tend to think I overdo things, that I overdress. I want to look sharp, I want to look stylish, I want to look fashionable, but do I go overboard at times as a result? Perhaps.

Case in point: A few days ago on President’s Day, I went to the local casino to have a little fun and spend a little money, and while pretty much all the women there were in purely casual, even frumpy or sloppy clothes, there I was in a nice sweater, a pencil skirt, hosiery and heels, even for a place as innocuous as a slots parlor, I just couldn’t bring myself to dress down. Or on another occasion at the King of Prussia Mall, I sported my black leather jacket over a turtleneck, a dressy a-line knit midiskirt and high heeled knee boots, and I can assure you that NO other female, young or old was half as put together as I was, even though I didn’t need to be, but, I can’t help dressing up for outings like to the mall. I’ve said this a time or two or a dozen, and I believe it to the max: when I look good, I feel good, since wearing women’s clothes is great fun, I want to do it right. Perhaps vanity plays a part in my habit of overdressing because I like to show off, to display my fashion style since I look better in women’s clothes than I do men’s, something that’s also fun as I just love strutting about in a skirt and heels, it’s a highly intoxicating feeling.

To everyone reading this piece, regardless of your level of commitment to freestyling, if you wear just one article of clothing or go the whole hog like I do, it’s important that you take pride in your appearance when out in public. That you put a premium in being knowledgable about fashion and looking your very best, because you’re setting an example to the whole world for men who wear women’s clothing, and that example should be we CAN look tasteful and stylish in the clothes we choose to wear and not odd, freakish or embarrassing. I don’t mind admitting I obsess over looking my best, I never go out unless I am, so, if that results in being occasionally overdressed for the surroundings I happen to be in, I don’t mind that at all. If anything, I’m rather proud to say I overdress, like everything when it comes to freestyling, it’s a thrill. Opinions?

Edited February 23, 2018 by JeffB

[nzfreestyler]

Well said JeffB !!!

My confidence to wear what I like stems from my belief that I present a polished look and that I can also wear my heels very capably.

Women are the harshest critics (of themselves and others) so I make an effort to dress well - if I'm playing in their realm I make sure I am up to their standards and preferrably higher.

Cheers

 

 

[Thighmax]

Unfortunately, I have only worn boots outside a few times.  I don't even know if someone noticed although I am pretty sure that a few people did.  One of the people that noticed was a woman standing behind me in line.  I know because she made an awful face when she looked down.

I have only now started buying leather skirts, pants and I have also bought dresses that I like.  I have never worn them outside though.  From my perspective, this type of clothing is almost always more stylish than the way we usually dress.  As an example, a few months ago, my wife and I dressed the same way, her shirt looked close to mine, so did her jeans and boots.  The only difference is that her jeans were skinny, but the boots were exactly the same.  We took some pictures, and you can clearly see that her look is way more polished than mine.  It has to do with tidiness, I think.  

I have been wearing my dresses more often now, and when I look in the mirror, it automatically looks more dressed up than any other type of clothing I use.  I do believe  as Jeff does, we like the clothes so much that we almost like to play with them and play "dress up".  

I don't really care, I love the way I look when I wear a dress.  It might look dressier than the average but I am dressing myself to make myself look good.  

I would say, carry on.  I love looking the best that I can every time that I dress myself.  There is never a second chance to make a "first impact"!!!!!

[CAT]

5 hours ago, JeffB said:

Here’s a question worth pondering: is being overdressed a bad thing? When I embraced the unique lifestyle of the fashion freestyler, I made it a point to always, and I mean ALWAYS look my very best. I mean, if I was going to traipse out in public wearing women’s clothes AS A MAN, then I’d damn well better make sure I didn’t look foolish or inappropriate. Because of that particular mindset, I tend to think I overdo things, that I overdress. I want to look sharp, I want to look stylish, I want to look fashionable, but do I go overboard at times as a result? Perhaps.

Case in point: A few days ago on President’s Day, I went to the local casino to have a little fun and spend a little money, and while pretty much all the women there were in purely casual, even frumpy or sloppy clothes, there I was in a nice sweater, a pencil skirt, hosiery and heels, even for a place as innocuous as a slots parlor, I just couldn’t bring myself to dress down. Or on another occasion at the King of Prussia Mall, I sported my black leather jacket over a turtleneck, a dressy a-line knit midiskirt and high heeled knee boots, and I can assure you that NO other female, young or old was half as put together as I was, even though I didn’t need to be, but, I can’t help dressing up for outings like to the mall. I’ve said this a time or two or a dozen, and I believe it to the max: when I look good, I feel good, since wearing women’s clothes is great fun, I want to do it right. Perhaps vanity plays a part in my habit of overdressing because I like to show off, to display my fashion style since I look better in women’s clothes than I do men’s, something that’s also fun as I just love strutting about in a skirt and heels, it’s a highly intoxicating feeling.

To everyone reading this piece, regardless of your level of commitment to freestyling, if you wear just one article of clothing or go the whole hog like I do, it’s important that you take pride in your appearance when out in public. That you put a premium in being knowledgable about fashion and looking your very best, because you’re setting an example to the whole world for men who wear women’s clothing, and that example should be we CAN look tasteful and stylish in the clothes we choose to wear and not odd, freakish or embarrassing. I don’t mind admitting I obsess over looking my best, I never go out unless I am, so, if that results in being occasionally overdressed for the surroundings I happen to be in, I don’t mind that at all. If anything, I’m rather proud to say I overdress, like everything when it comes to freestyling, it’s a thrill. Opinions?

You are 100% right in my book Jeff!!!!    If your going to go out look good.  My GF stresses about looking good when she goes somewhere.  And it’s dressed appropriately for where you are going and what you are doing. If she is teaching Pilates she’s in lululemon and looks fantastic.  If we are shopping she is dressed up but not over dressed.  Dress and boots or heels.   Leggings and boots with a sweater.  If we are out on the town she is dressed up to be out on the town.  As for me,,,,,,,, well you have seen the pics of when we are out in the town.  She says I stresss and think about it more then she does   I have to it’s not that easy to look as good as she does with 1/2 the effort.  Also I keep my outfits, depending on the activity in check as she is the important one not me.  We are going out shopping first today and I am wearing a men’s lulu shirt lulu leggings boot socks with my new Sorel Dacie heeled boots.   I’m taking another outfit to change for dinner and drinks 

Jeff, you always look fab in your pics.   If your going to get dressed you might as well look good!!!

[Heelster]

This is a good question, and I have to think a bit more about it.

I realize I live in an area where we don't really need to dress in anything more than jeans and t-shirts. Yes, that's a majority of my wardrobe, but I see no reason to wear anything better for fast food. What's scary is that I'm usually better dress than most of the folks around us. (Thank You Walmart)

Jeff and CAT - - - keep doing what you do.

Damned - - - A night out - - almost all of the places around here (what few there are) have former military insignia associated with it, and almost all have Harley parking in front.

[MackyHeels]

Agree with all here. Best to dress as your personal style dictates everyone fashion is different.  There is ways to wear outfits and trends and not appear awkward only takes experience.

When observing at times shopping  an older lady very well dressed, like she was going to a wedding, in light cream colours. Everyone shopping heads turned seeing her enter the shoe store at the mall. Most customers were casually dressed only sales ladies had similar outfits yet not in same manner as the older well dressed woman. I could tell from observing everyones reactions of the well dressed woman was of envy by many woman. Without a doubt the sales ladies would of complimented her with the outfit how well dressed she was if she bought something. Although the customers may have felt she was overdressed just to be shopping in the mall.  Only some may of thought she came from work maybe real estate agent or off to wedding etc...

Just observation some women have is fear being overdressed. Specifically i see it with asian young ladies. Often then not asian single females when out and about, feel the need to wear short heel pumps when out with friends. This often seen as awkward  no matter the location observing there lack of confidence. For example at my workplace seen these guests, one in particular stood out young attractive asian female standing in line with others her age. Many females were casually dressed no heels just denim jeans and low flat footwear for the most part. While i stared upon the asian female in her pink chiffon flowing low cut dress and nude pantyhose with amazing Stuart Weitzman crescent high  heel suede pumps i like  i so much was jealous of.  As i stared upon her more i could tell she noticed my reaction to her beautiful heels yet she may have misinterpreted staring down at them feeling insecure. 

She became bit unnerved maybe thought being way to overdressed for the occasion and venue and others in the lineup. Yet if she appeared more confident in the outfit and proud of the heels there would be no way others thinking of being overdressed would enter anyone's mind. Although her dress looked more appropriate for a wedding then the benign ceremony at work. Although think she had advice from her parents or mom that she should dress-up. Often through inexperience of locations and venues or the crowd asian young woman don't have outfits that suit  all occasion.  Sometimes outfit can appear to formal like her short cute dress but not at all suitable for the occasion. Something has to to be said about semi casual outfits ot comfortable yet dressy. Only takes experiences to figure out what works or often makes someone uncomfortable in.

 

 

Edited February 24, 2018 by MackyHeels

[jeremy1986]

Agreed to all of the above, though I have never dressed outside, and only heeled a couple of times. But even from my home heeling, I can tell that us guys prefer to dress it up with fancy heels and boots, whereas most women in the casual routines will wear comfy-wear with flats or sneakers, only dressing up when there is a reason for it. We on the other hand enjoy sporting our heels all the time!! but I think that's far from the norm of most women.

[Cali]

On 2/23/2018 at 1:46 AM, JeffB said:

I’d damn well better make sure I didn’t look foolish or inappropriate. Because of that particular mindset, I tend to think I overdo things, that I overdress.

Just to throw another log on the fire in your mind.

How appropriate is it to overdress? Is this what you're worried about? That you are being inappropriate by overdressing?  Tough question.

My version of "freestyling" I call blending. On almost every day at least 60% of what I am wearing stated out on the other side of the store. I present (alpha) male, but I like tighter fitting clothes, I like to layer, more color ... and these qualities I can find better in women's clothing. Since I started blending and wear high heels I find that I take more time in putting my outfits for the day together. Also, I dress better than I use to. Either matching my heels to what I have on or knowing what heels I want to wear dictate my outfit for the day.

[JeffB]

Thanks for the comments, everyone! I found them most intriguing and instructive as well.

When it comes to fashion, we, as men, are far behind the learning curve. When it comes to how to wear women's clothes and how to put together stylish and tasteful outfits, we're learning in our 30's, 40's, even 50's what women learned as little girls, so we have do a lot of cramming in order to catch up with them, if that's your ultimate goal. Not to brag, but I like to think I've done well for myself, nzfreestyler was spot on right, women DO notice and criticize what other women wear, and when we freestylers venture into their arena, we become subject to their critical eye, so far, I've escaped said criticism, in fact, I've been complimented on my outfits, shoes, jewelry, even my handbags, so I guess I'm doing something right. But, that doesn't mean I sit on my laurels, no sir, I continue studying, continue learning all I can about fashion so I continue looking my very best.

Edited February 25, 2018 by JeffB

[Mr. X]

I dont' know If what I wear is considered overdressed but I definitely don a complete outfit when I go out.

[Jessika]

As a woman, I find it pleasing to look attractive, yet not overdone, that is pending the occasion and or function of the night out. Love my heels whether in a dress or skirt or skinny jeans/pants. Be pleasing not fake looking

[Shyheels]

I work from home, unless I am travelling on assignment, and could wear rags if I felt like it. Wearing my nice boots in my home office gives me incentive to dress nicely overall - nothing fancy, just boots, jeans and jumper, that’s just my style - but put together neatly and thoughtfully and presentably. 

[MackyHeels]

Always wondered what shoe or heel would look phoney or overdressed with particular outfit or surrounding your in.

Read reviews of heels seeing if there any good often i come across specific statement woman leave. There afraid or find certain heels look to dressy for certain location. Such as they prefer a nicer outfit for the office before they wear them, or night out with the girls. Never considering wearing elegant heels to the grocery store or doing errands. In fact when i observe other woman it's true fact they rather wear a low chunky bootie for everyday walking around often seen sneakers flats etc...

Have two pairs of bootie crescent heels to choose from. One bootie suede constructed with heel three inches other in soft leather almost four inches of the heel. By looking at them in the store i found the Lofty shorter heel, suede constructed bootie bit more casual for everyday wearing. While the other called pure bootie higher heel leather constructed bootie little more polished and elegant both pointed toe styles.

 

So mindset of wearing stiletto heels needle style. Find black napa leather looks more casual then a patent leather which appears dressy. Sometimes compromise needs to be done going for suede fabric which appears casual. Then the outfit screams overkill pairing it with jeans. So a sandal heel dresses the outfit down makes it look better.

 

Do know either bootie would be fine for everyday wear. Suede bootie has rubber synthetic sole for better wearability, while the pure booties with napa leather has leathered smooth sole very elegant. Comes to my mind that higher heel napa leather bootie is to nice for, wear and tear for everyday use, only special occasions. Anyone have that mindset as me? Shoes are too nice to be wearing everyday use. Thus we call it dressy rather casual. 

Sometimes feel the shoes or heel goes out of style or trend before you get enough uses for the money paid. Sort of my shoes look new but should of worn them more often before buying the newest or latest trend. Anyone get what i'm saying. 

If they look good wear them to do errands or whatever but get most use out of it before you go out buying something newer or better.

 

Edited February 27, 2018 by MackyHeels

[nzfreestyler]

2 hours ago, MackyHeels said:

Sometimes feel the shoes or heel goes out of style or trend before you get enough uses for the money paid. Sort of my shoes look new but should of worn them more often before buying the newest or latest trend. Anyone get what i'm saying.

Yes I know - its a trap to go for cutting edge trends and fashion. I prefer to avoid 'fashion' and go for 'style' or 'classy' hence I love and wear pumps. Pumps go with pants, 3/4 pants, shorts, skirts, dresses etc... everything provided the heel height is appropriate.  Thats just my thoughts - oh - and pumps lengthen the leg more as anything around the ankle such as a bootie or even an ankle strap etc shortens the wearers legs which is why I don't have many ankle booties or pumps with ankle straps (maybe 10-15 shoes at most like that) and also don't wear that style much.

Nappa leather or patent (in a pump) is much dressier than suede I think. In boots patent has a 'hookery-ish' element dare I say it, so for me boots must be leather only, no patent or suede.

I wear heels all the time and truely suede shoes just get smashed.. especially suede on the heels. Most of my suede pumps have a stacked heel or a matching patent heel - but if the heel is suede it gets so dirty and damaged as it is not as durable as other materials. Also I find the toe area - the suede just gets wet/stained since high heels have super thin soles and moisture/dirt just gets on your shoes very easily in the toe area too. Again suede is really hard to look after. I base this on my heel wearing, which is all the time at wok and play and suede just doesn't cut it ever. Too damn hard to look after and too fragile for everyday situations. (might be different with a small platform? don't know - hate the damn things - don't wear any!)

The two booties above - I would wear the 2nd - the pointier to and the nappa leather is much classier - and will wear and keep better so is also the practical choice.

 

Edited February 28, 2018 by nzfreestyler

[MackyHeels]

T

16 minutes ago, nzfreestyler said:

The two booties above - I would wear the 2nd - the pointier to and the nappa leather is much classier - and will wear and keep better so is also the practical choice.

 

Thanks although i already own round toe black leather bootie Rag & bone harrows and in sand suede. Agree suede is terrible to look after rarely wear them because worried about the weather if it's going to rain or already wet streets outside etc.. 

The Pure booties i love them but at $700+ taxes price tag compared to 500 for the suede or just keep wearing my older tight ill fitting booties. Or buy a great 4" pump stiletto with smooth heel but suede black fabric which will make my outings very much overdressed but right price at $100 who cares if they ruin quickly.

Thanks for the feedback.

 

As for legs looking longer in booties or heels find my harrow booties are extension to my legs without making me appear stout. Helps when wearing ultra skinny jeans and i'm not covering my hips with a long top. Enjoy when i pass by mirror seeing my reflection, wow factor  bringing smile to my face  at how lean and contoured my silhouette appears. 

Edited February 27, 2018 by MackyHeels

[nzfreestyler]

On 2/25/2018 at 12:45 PM, MackyHeels said:

She became bit unnerved maybe thought being way to overdressed for the occasion and venue and others in the lineup. Yet if she appeared more confident in the outfit and proud of the heels there would be no way others thinking of being overdressed would enter anyone's mind. Although her dress looked more appropriate for a wedding then the benign ceremony at work. Although think she had advice from her parents or mom that she should dress-up. Often through inexperience of locations and venues or the crowd asian young woman don't have outfits that suit  all occasion.  Sometimes outfit can appear to formal like her short cute dress but not at all suitable for the occasion. Something has to to be said about semi casual outfits ot comfortable yet dressy. Only takes experiences to figure out what works or often makes someone uncomfortable in.

Its hard to wear womens clothes compared to mens. Womens clothing is much more fitted through the waist, fitted across you hips and bottom and generally punishes you (the wearer) more if you are not so well proportioned - or you choose a style that doesn't make you look your best. The vast range of styles also doesn't help as more choice makes it easier to get it wrong. At an office work environment women can wear full length pants, 3/4 pants, shorts, skirts, dresses.... men wear pants/trousers only (perhaps a few wear shorts but thats too casual). Then there's the shoe choices....the blouses/tops too.... Wearing a skirt/dress puts you legs out for all to see, and most shell tops/short sleeve blouses or dresses are shoulders/arms out for all to see too. Men are all covered up. Men don't have to worry about imperfections such as tan/ no tan, wrinkles, skin blemishes, hair on body etc.... guys do get it so much easier.

Thats why I believe many women are hesitant or nervous - be they under dressed or overdressed - they're nervous in what they are wearing regardless because they're not quite comfortable with their choice. They're trying something new perhaps - eg a shorter skirt than normal - or they're wearing a sheer blouse for te first time, perhaps a low plunging neckline, perhaps their feet are tired...high heels can be hard work - at work - I know. Perhaps they've just made a mistake and as you said they've gone a little more evening/dressy than others - perhaps they've got a dress on when everyone else is in pants....again everyone will notice them more - and they know that.

Thats the thing too - wearing womens clothes gets you attention - the cuts, the styles are attention grabbing. Men look - women look - both for different reasons - but everyone looks. It is nerve racking on one hand - but also so empowering on the other. Not everyone is comfortable or can embrace this attention and use it. This i think is why so many women don't wear high heels a lot - its the attention they are uncomfortable with - the lookers that have their eyes on them. Whether you're a guy or a girl wearing a dress and heels you will be looked up and down by everybody. Women judge you on your ensemble and presentation, guys generally check out your body....guys mostly objectify. Thats just the way it is - and thats what makes it hard. You the wearer need to want and/or be able to deal with the attention from everyone in order to be comfortable wearing what you choose. For women in general their clothing choices make it hard.

A good example/comparison is that at a formal dress level its quite likely that a guy will only have his head and hands exposed and be wearing a suit (hides a lot of imperfections in his posture/figure) wheras a womans attire might have her legs bare, arms bare, shoulders bare possibly full back exposed, bare feet in high sandals etc...or perhaps very covered up in a gown with only her shoulders and arms out - but still very fitted through he bust/waist/hips so we can see here figure..... its just not comparable - and the options only really become equal when we go to the really casual choices.

 

 

 

Edited February 27, 2018 by nzfreestyler

[nzfreestyler]

A high heel shoe/boot that does not create a block/line at the ankle or above the ankle will always lengthen your legs (and especially so when ones legs are out (skirt/dress/shorts)

A bold break/block such as a bare leg and a darker coloured bootie at/around the ankle WILL shorten the wearers legs. Eg a bare leg and any pump will lengthen the leg as there is unbroken skin tone from the knee to the toes - A nude bootie on bare leg for example would likely not fore-shorten the wearers legs because of the similar colour tones all the way, a ankle strap pump will have a line/lines around the ankles which draws attention to the ankle and the line shortens the continuation of the leg, a dark bootie will end the leg at the top of the bootie - above the ankle - shortening the wearers leggy-ness.

I think booties are best worn with the ankle and/or leg exposed - they need to be seen - so wear them with a 3/4 pant/jeans - fitted - or shorts/skirts so the bootie can be seen. Booties are all casual - not dressy - so their purpose is to subdue the 'out-there' look of an ensemble, eg a mini skirt or shorts with stiletto pumps is more sexy than a mini skirt with booties. The booties make it casual and tone it back.

If you're wearing jeans/long pants then a stiletto pump etc would be fine as your leg is covered - of course the damn problem with full length pants is the tailoring to suit exact heel heights sucks ! And then they can't be worn with any other heels ! (thats why I never wear long pants except for a few jeans) That the beauty and reason for 3/4 pants for women - alleviates the issues with high heels. Similarly why skirt suits are the best as it doesn't matter which heels you wear. Pant suits suck - horrible things - unless they're a tapered 3/4 pant.

[Cali]

I for one have about half a dozen suede heels and wear them on a rotational bases with my other boots and booties. Almost bought another pair yesterday, NOT RATED booties with tassels. And wore my blue suede knee highs today. I take care to only walk on pavement and avoid walking on grass. Then dry them out before putting them away.

[Shyheels]

Why is all the fashion talk here nearly always, and only, about wearing women's clothes?

Edited February 28, 2018 by Shyheels

[nzfreestyler]

13 minutes ago, Shyheels said:

Why is all the fashion talk here nearly always, and only, about wearing women's clothes?

Not sure exactly - for my 10 cents worth I think its because high heels are a delicate looking shoe - and they make the feet look much smaller - this can look very awkward on top of bulky mens fashions - all big/baggy top half etc slimmed down to tiny feet ... looks funny perhaps ? Whereas wearing clothes more usually defined as womens are fitted, have a finer silhouette and balance your high heeled legs better? Not so heavy/bulky looking ?

Besides - if I'm wearing a skirt its my skirt - I don't see it as womans clothing per-se.

[nzfreestyler]

31 minutes ago, Cali said:

I for one have about half a dozen suede heels and wear them on a rotational bases with my other boots and booties. Almost bought another pair yesterday, NOT RATED booties with tassels. And wore my blue suede knee highs today. I take care to only walk on pavement and avoid walking on grass. Then dry them out before putting them away.

I know what you mean - but the suede still gets stuffed when you wear them a lot. I've dozens of heels that are either satin or suede and the suede gets abraised easily - and the former, the satin heels are typcally dressier but they too stain easily and can get scuffed. I never walk on grass etc (also avoid gravel etc) - I take the long way around or I don't go there but my pumps still get damage - especially around the sole where the forefoot touches the ground - lots of little blemishes and watermarks from winter or scratches etc...

Kidskin / Patent pumps definitely wear the best - so too do fabrics like lace overlays - they are durable.

 

[Shyheels]

Nzfreestyler: Block heeled boots don't seem particularly delicate - and they're high heels. Stilettos are more delicate, true, but surely they can be worn with jeans - plenty of people do. There is a post in another thread about a banker in Sydney who wears stilettos with his business suit and judging by the picture he looks quite presentable. For a site that ostensibly isn't about cross-dressing there is a huge - indeed overwhelming - emphasis on men wearing women's clothing here. 

And yes, I get the idea that if you own a skirt it’s yours and not a woman’s, but you do in your posts refer to “women’s clothes” so clearly you do understand the distinction.

Edited February 28, 2018 by Shyheels

[nzfreestyler]

gidday Shyheels,

I see what you mean - but my point is that even a block heel is 'delicate' because the heel style is kind of immaterial to the shoe - any high heel is going to make the wearers feet look smaller. The higher the heel the smaller the foot appears and it becomes more leg - especially with pumps/sandals.

I've nothing against heels and jeans - I wear stilettos with jeans as its a good combo. A fierce shoe with a covered leg is still casual.

As far as cross dressing goes - well, as I understand it - that implies wanting to impersonate a woman and 'pass as one'. Who said anything about wanting to impersonate a woman. As I understood it the discussion was just around the clothing, of which shoes are a part too. I thought that the folk here are into doing what they do as they do and as themselves, no attempts to impersonate.  This is why I refer to myself as a freestyler - I'm pretty mixed up when it comes to clothes!

cheers

[Heelster]

25 minutes ago, Shyheels said:

Block heeled boots don't seem particularly delicate - they're high heels. Stilettos are, but surely they can be worn with jeans - plenty of people do. There is a post in another thread about a banker in Sydney who wears stilettos with his business suit and looks quite presentable. For a site that ostensibly isn't about cross-dressing there is a huge - indeed overwhelming - emphasis on men wearing women's clothing.

I wear men's industrial uniform jeans all day. Definitely not flattering by any means. Just functional. They don't look right with any heel I own. Men's dress pants - - especially if the have pleats of any kind look like hell on me, and the wife wouldn't let me out of the house in them. They look that bad on me. Last time I wore a suit or Tux was 1986.

Women's jeans on the other hand fit me better, look better, and work well with any footwear I go out with. Nobody has ever noticed these that I am aware of. I can pull off skinny jeans as long as they are not ""too skinny"" in the calf. Wife loves these so it's all good.

In the last couple years. I have discovered leggings and jeggings, which are super comfortable. I find legging leave me with a profile just below the waist that would not be  - - lets just say not suitable in public. A denim mini skirts cleans this up well, but I could never wear this in the local village without catching the wrath of God and a ton of negative reaction - - Trust me on this one. I could pull it off at a Chicago heel meet with a variety of heels I have.

I have never ventured out and about beyond women's jeans with heels. Usually in T-shirts and pullover polo's. Wife wouldn't appreciate me wearing much else from the other side of the aisle, and unless I show up at a meet such as Chicago as an example, I'm not likely to do so solo.

For me it's not cross-dressing - - it's fit and function with a splash of heel.

[nzfreestyler]

Yeh I hear you Heelster.

I have evolved over a good decade and a half into my style, which has gradually evolved more into skirts and dresses because - well - they're just better to wear. Wearing a skirt suit for work was the hardest & most exciting change I went through - but it was surprisingly easy in hindsight.

I guess I am fortunate that I was able to break out and wear what I felt like ages back and I've been fortunate to never have any issues I would rate as significant enough to put me off wearing what I feel like. I have often pondered on what else would I do/ might I do, because I know I am wearing typically womens clothes and I have no interest in cosmetics/ wigs etc - I'm totally happy in the space I'm in. I've kind of gone out there and selfishly worn just what I wanted to and its been fun and hopefully should continue to be (touch wood).

[Shyheels]

I live in jeans myself and hundreds of thousands of miles of cycling has given me legs fit and slender enough so that even though I am decades away from adolescence I can still quite readily get away with wearing skinny jeans, and I do so. The cultural distinction between men’s and women’s jeans, I have to agree, is kind of irrelevant and usually exists only in a marketer’s eye and pricing strategy. 

But when I read this thread and see only women's clothes being discussed and then cast my eyes over the subject lines of other threads in the General Fashion forum and see topics such as - skirts, pantyhose, corsets, nail polish, leggings, gowns and ‘androgynous help’ I start to wonder...

Edited February 28, 2018 by Shyheels

[Shyheels]

36 minutes ago, nzfreestyler said:

gidday Shyheels,

I see what you mean - but my point is that even a block heel is 'delicate' because the heel style is kind of immaterial to the shoe - any high heel is going to make the wearers feet look smaller. The higher the heel the smaller the foot appears and it becomes more leg - especially with pumps/sandals.

I've nothing against heels and jeans - I wear stilettos with jeans as its a good combo. A fierce shoe with a covered leg is still casual.

As far as cross dressing goes - well, as I understand it - that implies wanting to impersonate a woman and 'pass as one'. Who said anything about wanting to impersonate a woman. As I understood it the discussion was just around the clothing, of which shoes are a part too. I thought that the folk here are into doing what they do as they do and as themselves, no attempts to impersonate.  This is why I refer to myself as a freestyler - I'm pretty mixed up when it comes to clothes!

cheers

Gidday

I get the idea of each to their own, and that people should not be bound up by convention but be free to dress as they please. This forum is wonderful for that, and the participants invariably friendly and supportive of each other.  But the near-constant emphasis on men wearing women’s fashions and clothing is not only heavily suggestive of cross dressing - whatever the official definition - but is also a one-note gong, because surely there are men’s fashions that work well with heels and boots. It isn’t all bad. And if one truly wants to regularise the idea of men wearing heels, make it acceptable and commonplace in society, then one has to start with basics and work from there, make the idea accessible and attractive to the rank and file. That’s really where this forum could come into its own.

Edited February 28, 2018 by Shyheels

[nzfreestyler]

I do get your point.

Likely a inspection at top level can look worse - these clothing articles/categories discussed are all more womanswear - for sure - but I'm guessing based on myself as an example - you won't find people on all threads. Some may be into skirts/dresses such as myself, others makeup, others vintage corsets perhaps etc ??

It doesn't mean its outright all womens fashions. I suspect everyone has some component in their mix because heels are involved after all, but not necessarily all of these topics.

Whay aren't there mens clothing threads then? I would happily discuss mens fashion items in conjunction with high heels etc.. but truthfully I don't have nay traditional menswear (except for some fitted jeans and graphic t shirts) that I would wear with heels. The clothing choices are just too bulky looking (in my opinion). I wear anything I think works so I would not hesitate to wear a garment if I liked the look of it, but I just don't find menswear suits my style much - apart from very casual wear - buts thats when I'm at home (and I don't wear heels at home).

Sorry - kind of wish I had some examples of menswear but I don't ?!

 

[Shyheels]

I'm not cherry-picking the topics here. Looking further down the list one sees:  The Wonder of Women's Clothes, The Dynamics of The Dress, Handbags, two more threads on nail polish and then, going onto the next page, we find more threads on skirts, handbags, leggings and fake nails. All worn by men. Each to their own and all that, and, yes, I realise that the definition of cross-dressing is subjective with some people thinking that a man wearing dresses and skirts is not cross-dressing and others thinking that a guy wearing so much as a pair of woman's socks is crossdressing, but surely the entirety of men's fashion cannot be bad, ugly, ill-fitting and inimical to wearing heels.  And again, if one truly wanted to normalise the wearing of heels by men, one needs to find as much common ground as possible with fashion as it exists today and for the vast majority of men. That is where this forum could truly come into its own and make a difference.

Edited February 28, 2018 by Shyheels

[RonC]

I do not own any women's clothing.  I will occasionally borrow a skirt from my wife if I feel like looking more feminine in a pair of heels.  I don't wear it out of the house (well, ok, I've gone to the bank drive-through in a skirt before - would be interesting if I had a fender bender or something and had to get out of the car..lol).  When I wear heels out, it is typically with long jeans, as I am not one to want to be noticed.  However, I will say that, in my opinion, a pair of men's dress pants or a suit pants look quite good with a pair of heels - of most any style.  I've seen examples here of both block heel boots and stilettos, and I think it looks just fine.  While not so common any more, for a number of years women were wearing heels with dress slacks and it looked just fine, and still does.