The Man in the Dress

Discussion of fashion elements and looks that are traditionally considered somewhat "femme" but are presented in a masculine context. This is NOT about transvestism or crossdressing.

The Man in the Dress

Postby JeffB1959 » Wed Jun 26, 2019 8:28 am

I am a man. And I wear dresses. Nothing more complicated than that.

When I began my journey as a fashion freestyler, I’ll admit that dresses were at the bottom of my wardrobe totem pole, mostly because I didn’t quite feel comfortable wearing them in public like I had skirts, and, at the time, I was fine with that. From 2011 when I donned a dress for the first time through 2016, I only wore them seven times compared to 209 outings in skirts, but, as I grew more comfortable in dresses, I began wearing them more, 2017 marked the first year of double digit outings with 10, followed by 27 in 2018, and so far in 2019, I’m at eleven and counting, and, as a result, my mindset about what I chose to wear on jaunts slowly began changing. Just as I evolved from jeans to skirts, finding the latter more enjoyable to wear, I’ve slowly come to prefer dresses to skirts, when I plan for an outing these days, I often choose a dress first, it’s a ridiculously uncomplicated garment, you don’t have to rack your brain worrying about pairing the right top with a skirt, you just slip into a dress, put on shoes and go, easy as that. What could be simpler?

I don’t at all hide or mask that I’m a man in a dress. Sure, I augment that garment with high heeled shoes (though not always), jewelry, handbags, even the occasional dalliance with lipstick, but that’s as far as I go, I’m all about the garment first and foremost which is at the center of my current existence as a fashion freestyler. I’ve said more than a few times in my thread over on High Heel Place, and I believe wholeheartedly that I look better in women’s clothes than I do men’s, and I go to great lengths to look my very best in the former while it’s often a struggle to care how I appear in the latter. When I don a dress and see myself in the mirror, I never fail to like how I look which, in my mind, is a look that’s perfectly natural, like I’ve been wearing dresses all my life instead of just the last few years. Staring at my reflection, I see a man who’s totally comfortable and at ease defying gender norms when it comes to what men should or shouldn’t wear, if anything, being a man who wears dresses in public as a man displays a special brand of machismo, after all, it takes colossal balls for a guy to parade around in the open in a dress, and make it look like it’s no big deal to boot.

I’ve said numerous times that the final stage in my evolution as a fashion freestyler would be to one day completely abandon my skirts and elevate to wearing dresses full time on my outings, hell, I even long to wear an evening gown to some fancy social function and turn heads with my style and boldness, that would be downright awesome! With each new adventure, the pull of the dress grows stronger and more irresistible, however, I’m not forcing things, preferring to let that last stage come in its own good time so I can fully enjoy the experience. But, it will come, of that, I have absolutely no doubt, and when it does come, my journey as a freestyler will be complete. Short and sweet, I am the man in the dress, and I am VERY proud of that title, for it is who I ultimately am in this world.
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I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Man in the Dress

Postby SkirtNV » Wed Jun 26, 2019 2:08 pm

Wow. You look good.
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Re: The Man in the Dress

Postby new2skirts » Wed Jun 26, 2019 3:59 pm

You look good, but don't abandon skirts!! Dresses are nice but there is a variety of skirts to enjoy :)
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Re: The Man in the Dress

Postby beachlion » Wed Jun 26, 2019 4:48 pm

SkirtsDresses are still a bridge too far for me. Not only do I have to change my mindset but also my wife and friends will have problems with it. I made a few dresses and I'm also looking to order a simple dress but this is not the moment for me.

P.S. I noticed the first word made no sense at all. So I changed it. I think I'm too trigger happy with the Enter button. ;)
Last edited by beachlion on Wed Jun 26, 2019 10:13 pm, edited 1 time in total.
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Re: The Man in the Dress

Postby Freefrom » Wed Jun 26, 2019 7:31 pm

I have to say that you look very much at ease in all of your photographs and the clothes you choose suit you very well.
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Re: The Man in the Dress

Postby JeffB1959 » Thu Jun 27, 2019 8:28 am

Thanks for the kind words, everyone! Much appreciated.

beachlion: Men wearing dresses aren't for every man, I'm lucky I can make that work and look good at the same time. I neither encourage or discourage guys here to follow in my footsteps and wear dresses, it's all up to the individual and their level of comfort in such a garment. But, if you do choose to wear a dress, it's vital that you do it RIGHT.
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Man in the Dress

Postby Kilted_John » Thu Jun 27, 2019 9:22 am

You can always wear a shirt over a sleeveless dress (tank, spaghetti strap, or no straps at all) and turn it into a skirt. Did that tonight with the dress I'm wearing at this time. Threw on a t-shirt and it became a lightweight skirt.
Skirted since 2/2002, kilted 8/2002-8/2011, and dressed since 9/2013...
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Re: The Man in the Dress

Postby beachlion » Thu Jun 27, 2019 4:30 pm

I'm used to tuck in my shirts so using a shirt or T-shirt over a dress did not come up in my mind. I'm a little dense now and then. But I will try it and see how it goes. In the technical field I'm fast to grasp new ideas but in other areas I'm slow. ;)
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Re: The Man in the Dress

Postby beachlion » Sat Jun 29, 2019 4:15 pm

I just came up with another way to get into dresses: a dress in stealth mode.
I started with kilts. My wife liked it. To make the step into skirts I made a sort of wrap around skirt in the same form as a kilt. My wife tolerated and accepted it. Then denim skirts and so I came to the point where I'm now.
I tried a few dresses I already made with a shirt or T-shirt over it. Most shirts and T-shirts are too long and also too warm. The shirts have slight shirt tails and I don't like the sight of it untucked. So this is not the way to go.
Then the stealth idea came up. If I made a dress from two components, a sort of shirt and a skirt connected at the waist. I could use two different colours of denim or a checkered fabric for a sort of T-shirt and plain denim for the skirt. I could even fake a belt of fabric. And a vertical zipper from top to bottom for ease of putting it on.
All new developments I have to "sell" to my wife (and some of her friends) in order to keep the peace in the house. I hate it to force something on her.
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Re: The Man in the Dress

Postby Fred in Skirts » Sun Jun 30, 2019 2:40 am

Today was a bad day for me, I had to take the trash to the compactor and when I went to start the car it was as dead as the proverbial doornail. So When I finally got my neighbor across the street on the phone he said he would be right over. I was wearing my wrinkle dress and he has never seen me in a dress, a skirt yes but never a dress. When he and his wife came over nothing was said about the dress.
The car however still would not start so they went back and brought his truck and it still would not start the car. So he took the battery out of my car and took back to his place and said he would charge it all night. Then come back on Sunday and put it back in the car, I will be dressed in a dress then too.

I was going to the compactor in the dress I had on.

Fred
Fred :kiltdance:

:whistle: Hi I am Fred and I wear skirts and dresses all of the time. :hooray:
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Re: The Man in the Dress

Postby dillon » Mon Jul 01, 2019 2:06 am

beachlion wrote:I just came up with another way to get into dresses: a dress in stealth mode.
I started with kilts. My wife liked it. To make the step into skirts I made a sort of wrap around skirt in the same form as a kilt. My wife tolerated and accepted it. Then denim skirts and so I came to the point where I'm now.
I tried a few dresses I already made with a shirt or T-shirt over it. Most shirts and T-shirts are too long and also too warm. The shirts have slight shirt tails and I don't like the sight of it untucked. So this is not the way to go.
Then the stealth idea came up. If I made a dress from two components, a sort of shirt and a skirt connected at the waist. I could use two different colours of denim or a checkered fabric for a sort of T-shirt and plain denim for the skirt. I could even fake a belt of fabric. And a vertical zipper from top to bottom for ease of putting it on.
All new developments I have to "sell" to my wife (and some of her friends) in order to keep the peace in the house. I hate it to force something on her.

May I suggest you start with a long (ankle length) tank dress and wear a tee shirt over top. She may like that look on you. Then you've got "a foot in the door" so to speak.
As a matter of fact, the sun DOES shine out of my ...
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Re: The Man in the Dress

Postby beachlion » Mon Jul 01, 2019 2:36 am

dillon wrote:.......
May I suggest you start with a long (ankle length) tank dress and wear a tee shirt over top. She may like that look on you. Then you've got "a foot in the door" so to speak.


Thanks for the suggestion but my wife is not ready for skirts that look like skirts. One of the reasons she accepts/tolerates my denim skirts is they look like denim shorts. What I'm aiming for is something in denim and a little above the knee. First I will experiment with a two-tone dress. I ordered fabric and I will make my first attempt to acceptation.
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Re: The Man in the Dress

Postby Gusto10 » Mon Jul 01, 2019 6:16 am

beachlion wrote:
dillon wrote:.......
May I suggest you start with a long (ankle length) tank dress and wear a tee shirt over top. She may like that look on you. Then you've got "a foot in the door" so to speak.


Thanks for the suggestion but my wife is not ready for skirts that look like skirts. One of the reasons she accepts/tolerates my denim skirts is they look like denim shorts. What I'm aiming for is something in denim and a little above the knee. First I will experiment with a two-tone dress. I ordered fabric and I will make my first attempt to acceptation.

BL,
How would your wife react to bermuda's (= skirt with centre guard)? It could be a nice compromise...
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Re: The Man in the Dress

Postby dillon » Sat Jul 06, 2019 2:25 am

Given the diametrically opposed positions, I’d say one or both of you will be unhappy.
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Re: The Man in the Dress

Postby beachlion » Sat Jul 06, 2019 3:03 am

dillon wrote:Given the diametrically opposed positions, I’d say one or both of you will be unhappy.


There is a secret to this situation. It is called compromise. I brought some with me when I moved from the Netherlands to the USA. I had the impression there was not enough in the USA. ;)
In the end nobody will be happy but also nobody will be unhappy.
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