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JeffB

The Man in the Dress

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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, 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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Jeff,  I like your opening line.  Simple and to the point.  I admire your "courage" and tenacity to do what you enjoy, go public in women's dresses as a guy.  Plus you look fine doing it.  I have thought about giving it a try, but not certain that I could pull it off.  Maybe someday, for now I will just stick to wearing heels (in public !!) wow - what a thought.  

Take care, nice post....    sf

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Reading the title made me feel like I was in High School AP English class again. Glad you are satisfied with your style evolution!

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6 hours ago, SF said:

Jeff,  I like your opening line.  Simple and to the point.  I admire your "courage" and tenacity to do what you enjoy, go public in women's dresses as a guy.  Plus you look fine doing it.  I have thought about giving it a try, but not certain that I could pull it off.  Maybe someday, for now I will just stick to wearing heels (in public !!) wow - what a thought.  

Take care, nice post....    sf

Thanks for the kind words. The first sentence should always be an attention getter, and that was my goal. Meanwhile, I’ve said this before in my thread, and it bears repeating, wearing dresses (or skirts) isn’t for every man, I neither encourage or discourage others here from following in my footsteps, this is a journey I’ve undertaken by myself, I cannot expect others to do as I’ve done, that choice is wholly up to the individual. I’ve derived a special enjoyment from fashion freestyling, but I can’t say if others would feel likewise.

5 hours ago, kneehighs said:

Reading the title made me feel like I was in High School AP English class again. Glad you are satisfied with your style evolution!

Glad you were able to experience a memory. And yes, I’m very happy with my evolution. There is no turning back from the course I’ve taken as a freestyler, nor would I even think about such a thing.

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Posted (edited)
14 hours ago, JeffB said:

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 think @nzfreestyler would echo this as well. I have a friend that she says this to me all the time since I wear my heels all the time and I have colorful (wild) nails. At times it not easy, but I wouldn't have it any other way. I enjoy my heels, my nails and  my ....

Edited by Cali
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I think both JeffB and nzfreestyler both look great in dresses and their legs are consistently a bit nicer than mine. I enjoy dressing completely and then changing back to rural guy doing chores outside the very next day. Both JeffB and nzfreestyler make their marks in a very public way whereas I am not so much. All three of us enjoy the heck out of our clothes :fine: HinH

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