The Wonder of Women's Clothes: My History

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.
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JeffB1959
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The Wonder of Women's Clothes: My History

Post by JeffB1959 »

Time for a confession: I'm a man who loves wearing women's clothes...as a man. Perhaps that makes me a crossdresser or a transvestite, but I don't need to don a wig, put on makeup or strap on a padded bra, just the act of wearing the clothes alone is more than enough of a thrill for me. To wear a skirt or a dress is positively exhilarating; to hear the clicking of high heeled shoes on my feet is intoxicating; and the heft of a full handbag on my shoulder is pleasurable. And the fact that I venture out in public garbed in women's attire from head to toe is exciting in ways I can't possibly describe, and, heaven knows I try, real hard. This is the true extent of my existence as a fashion freestyler, and I love every minute of the experience.

My special journey as a fashion freestyler began years ago with just the shoes, and, in the beginning, I thought that would be enough to satisfy me, but, as time went on, I came to realize that wearing my heels with men's clothing, dull, boring, colorless and hopelessly static just wasn't enough, I needed more. That was when I ventured into skirt wearing in the latter half of 2008, more of a crazy personal dare than anything else, that first outing in a simple denim skirt (which I still have, by the way) was fun for me, mainly because of how the skirt looked on me, and how I liked what I saw, from that moment on, I started integrating skirts into my routine, they looked good on me, and I desired to wear them more and more, experimenting with various lengths, short, very short, knee length and maxi length, pairing them with pumps and boots, that was the beginning of my exploration into fashion freedom, but even that wasn't enough since I was wearing men's tops with the skirts and footwear. I decided I had to branch out more to satisfy the demands of my thirst for fashion, to see just how far I could take this passion that was welling up inside me, and I wasn't about to stop. It was so much fun.

That inevitably lead to women's tops: sweaters and turtlenecks in fall and winter, and when spring and summer came around, t-shirts, blouses and my favorite, tank tops. Again, I wouldn't wear such articles of clothing if I didn't think I looked good in them, and, being rather critical about my appearance, I made damn sure that I was happy with my appearance, otherwise, I didn't leave the house. Period. Hosiery was already part of the equation as I often wore knee highs under my pants and jeans, but when I gravitated to skirts, pantyhose became a must, followed by tights to keep my legs warm in winter. At the risk of sounding egotistical, as good as my long legs look bare, they're sensational when I've got hose on. Purses and handbags were next as part of the evolution since pockets on skirts were small, and it looked gauche, even silly to stuff items like my wallet, keys and smartphone, just to name a few items into them. Another confession: early on, I'll admit to being more self conscious about being seen with a handbag than I was about wearing a skirt and heels, but that anxiety quickly faded. In fact, I've gotten so used to carrying handbags, I don't feel dressed without one.

The final part of the equation were dresses. Since I was already comfortable in tops and skirts, able to go practically anywhere I saw fit without encountering any unpleasantness, I thought it was time to push the envelope by going out in a dress. That first outing was in a sleeveless black sheath from Sears with a gray blazer and a pair of black patent heels, that journey was most enjoyable, mainly because I went out of my way to look the very best I could, and, having achieved that goal, I realized that I looked good in that dress, and that filled me with plenty of confidence to brave the outside world. That lead me to wearing dresses whenever I could, one of my more pleasant outings was in a black cowl neck sweater dress with hose and a pair of high heeled knee boots, and, to say the least, I looked damn sharp that day. Since then, I decided to integrate dresses more into my repertoire. The bottom line here is that there is something incredibly special about wearing women's clothes in public as a man, it says I'm bold enough to ignore gender assignation when it comes to clothing and wear what I like, not what society says I should. And I fully appreciate that special brand of boldness.

There's a true wonder to women's clothes, the colors, the styles, the fabrics, how wearing them helps me feel softer, gentle and happier while putting me in touch with my feminine side. I can't help but feel uplifted when I wear these clothes, like they put me on an entirely different plane of existence. I never fail to feel elated when I come and go as I please, dressed how I like without any trouble or negativity, I believe that because I go out of my way to present the utmost when it comes to a tasteful and proper image, people accept me for my appearance, or choose not to bother with me, nevertheless, I'm pleased with the outcome. Now, I have to stress that not everyone can, or should do what I do, perhaps I'm an anomaly, a rarity when it comes to the concept of men who choose not to be constrained by the clothing and footwear society demands we wear. I'm extremely proud to be one of those men who've fully embraced the concept of fashion freedom, I take tremendous pride in wearing women's clothes (but when I wear such articles, they're just MY clothes), and letting the world see me in them. And the feeling is wonderful!
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Wonder of Women's Clothes: My History

Post by moonshadow »

Wonderful story Jeff! A lot of what your wrote I could have said for myself! I too enjoy the feeling if getting in touch with the feminine side of me, and generally feel quite free spirited when I'm wearing my outfits. While our core styles are somewhat different, (you wear nice "office appropriate" clothes, and I tend to wear what one might wear at Woodstock :lol: ), our reasons for wearing said clothes seem to be almost exactly the same!

*fist bump* 8)

P.S. I also like carrying a handbag (purse). In all seriousness, carrying a billfold around in your back pocket is bad for your back. I know when I would take long rides in the car, my back would begin to hurt. I removed the billfold and put it in the console and I felt immediate relief. I would love to carry a purse all of the time, even while working just for the back relief, but alas, someone would complain and I'd probably get the ax for that.... In the world of southern commerce... rigid gender roles appear to be more important that personal health and comfort. :roll:
-Andrea
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JeffB1959
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Re: The Wonder of Women's Clothes: My History

Post by JeffB1959 »

moonshadow wrote:Wonderful story Jeff! A lot of what your wrote I could have said for myself! I too enjoy the feeling if getting in touch with the feminine side of me, and generally feel quite free spirited when I'm wearing my outfits. While our core styles are somewhat different, (you wear nice "office appropriate" clothes, and I tend to wear what one might wear at Woodstock :lol: ), our reasons for wearing said clothes seem to be almost exactly the same!

*fist bump* 8)

P.S. I also like carrying a handbag (purse). In all seriousness, carrying a billfold around in your back pocket is bad for your back. I know when I would take long rides in the car, my back would begin to hurt. I removed the billfold and put it in the console and I felt immediate relief. I would love to carry a purse all of the time, even while working just for the back relief, but alas, someone would complain and I'd probably get the ax for that.... In the world of southern commerce... rigid gender roles appear to be more important that personal health and comfort. :roll:
It's good to find a kindred spirit when it comes to fashion freestyling. As for my particular style, yeah, I would define it as "office appropriate" as I like to look dressy, but, there's nothing wrong with your free spirited Woodstock style. Each and every one of us here marches to the beat of our own drummer. Oh, I keep my wallet in my front pocket when wearing pants, I've never felt comfortable or at ease with it in the back pocket. FYI.
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Wonder of Women's Clothes: My History

Post by Orange Apple »

Thanks, Jeff. Your thoughts mirror mine pretty much exactly, although I am much earlier in the journey than you are. You give me a glimpse of what is ahead for me.

A few decades ago, when the term "personal assistant" was born (think "Palm Pilot") I carried a purse for a while. The rationale for it was the bulk of stuff that it was common for everyone to tote around, but the real reason was to explore the concept of carrying a purse, something that, like wearing a skirt, was denied to men. Unfortunately, I kept forgetting about the damned thing, and leaving it behind. Unlike women who were indoctrinated from their earliest childhood in the idea that they needed to keep track of their purse, I never really got into the habit. But I bought my first skirt without pockets the other day, so I'm going to have to give it another go. Maybe the fact that I'm wearing a skirt will remind me to keep track of the purse.
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Re: The Wonder of Women's Clothes: My History

Post by Judah14 »

Regarding carrying purses, I prefer using a satchel instead, as it solves the problem of discomfort caused by carrying stuff in pockets while allowing me to free my hands up for other uses.
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Re: The Wonder of Women's Clothes: My History

Post by Fred in Skirts »

Wow Jeff you know how to really dress and all of the styles in the pictures you have posted are out of sight. I tend to be comfort driven in what I wear and am not a fashion slave in any way. I wear skirts with tee shirts, sport shirts, tank tops, and blouses of various types. The only male item is the sport shirts, all of the rest come from the other side of the aisle. As for shoes I wear flip flops, or mens boat moccasins. Getting shoes big enough and WIDE enough in womens shoes is imposable for me, I have looked at all of the shoe stores including the one that Moon likes. I can find the length but not the width in styles that I thought would be in my comfort zone. I like flat strapy sandals with out the shiny doodads. I also like the soft slip on shoes similar to the last pair that Moon bought.

I am also from PA, a little place known as Upper Darby, just out side of Philly. :hide:

Fred :kiltdance:
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Re: The Wonder of Women's Clothes: My History

Post by JohnH »

moonshadow wrote:Wonderful story Jeff! A lot of what your wrote I could have said for myself! I too enjoy the feeling if getting in touch with the feminine side of me, and generally feel quite free spirited when I'm wearing my outfits. While our core styles are somewhat different, (you wear nice "office appropriate" clothes, and I tend to wear what one might wear at Woodstock :lol: ), our reasons for wearing said clothes seem to be almost exactly the same!

*fist bump* 8)

P.S. I also like carrying a handbag (purse). In all seriousness, carrying a billfold around in your back pocket is bad for your back. I know when I would take long rides in the car, my back would begin to hurt. I removed the billfold and put it in the console and I felt immediate relief. I would love to carry a purse all of the time, even while working just for the back relief, but alas, someone would complain and I'd probably get the ax for that.... In the world of southern commerce... rigid gender roles appear to be more important that personal health and comfort. :roll:
You might get yourself a men's canvas messenger bag for work.

http://www.ebags.com/category/messenger ... s/m/canvas

In no way, shape, or form do those bags look feminine.

John
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Re: The Wonder of Women's Clothes: My History

Post by crfriend »

Of note is that European guys have been carrying bags for decades. There is no stigma attached to it whatsoever.
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Re: The Wonder of Women's Clothes: My History

Post by moonshadow »

JohnH wrote:You might get yourself a men's canvas messenger bag for work.

http://www.ebags.com/category/messenger ... s/m/canvas

In no way, shape, or form do those bags look feminine.
I appreciate the advice and ideas... however this is a matter of principle. I shouldn't have to make such strides to appease people with no real grasp of personal liberty nor capacity of abstract thought. In all honesty, why should I spend additional money on another "pouch" when I have a perfectly good small purse at home that works just fine? Only so the flat Earth'ers can sleep at night knowing that there are STRICTLY two types of people MALE and FEMALE, and God forbid if anyone blurs the lines!

Sorry... I need to eat... :eye:

*cue the snickers commercial* :lol:
-Andrea
The old hillbilly from the coal fields of the Appalachian mountains currently living like there's no tomorrow on the west coast.
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Re: The Wonder of Women's Clothes: My History

Post by Caultron »

I have a couple of "messenger" bags myself -- one black leather, one brown -- and they are cut a little differently than women's purses. They're usually quite rectangular, for example, and they're usually cross-body with fairly thick straps.

But they're still a lot like purses. 100%, actually.

But neither one has ever received any public attention.

But I still only carry them when a skirt doesn't have enough pockets.
Courage, conviction, nerve, verve, dash, panache, guts, nuts, balls, gall, élan, stones, whatever. Get some and get skirted.

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Re: The Wonder of Women's Clothes: My History

Post by Pdxfashionpioneer »

Hello Jeff, I identified with a lot in your story.

I found it interesting that early on you too felt more self-conscious about your purse than your skirt. I can't tell you how strongly I felt that when I rode with a fellow I barely knew, at the time, to our church's Men's Retreat. It was the first time I went there (it won't be the last) but nonetheless I wore a skirt and packed my denim shirtdress. I also packed pants. Riding out we made one stop after another to pick up various items for the weekend, other riders, etc. and while I would occasionally feel a little self-conscious about my miniskirt, I always felt quite self-conscious about the purse. Somehow it felt girly and the skirt didn't so much. (I hope we have a psychologist in our forum who can explain that to me.)

Once I got to the place we rented for the weekend I changed into the pants I had packed until I got acquainted with the other fellows on the retreat.

Fortunately, the next morning someone turned on the Michigan game so I had to change into something blue for my alma mater and wouldn't you know it, the only thing I had that was blue was the shirtdress. Ya gotta go with your team's colors, right?

Anyway, the only thing that was said about my change in attire, "Over Men's Retreat we sure learn what everyone's passionate about!" was so subtle I missed it until I thought about it later and realized it was a double entendre. I don't really follow football, but when Michigan's playing on TV I tend to get LOUD! So I first thought Rev. Tom meant Michigan. Later I realized he probably also meant my dress.

Nonetheless, once it was out of the (duffel) bag I wore it most of the rest of the weekend without any other notice or comment.

But I digress. To get back to my original point, I have to say Jeff, you put together some great looks and pull them off exceptionally well. You also articulated what a lot of us feel about wearing skirts. You've also reinforced my thinking about getting some nice blouses to go with my suit skirts. Until recently I thought, "What's the point, white is white and cufflink shirts looks great with my skirts!" (I love cufflinks, but they're not practical business attire when you pound your own keyboard or do a lot of writing.), but the women anchors on CNN have been making me think, "What could a white blouse or two cost anyway? And the fabrics ... "

You've sold me Jeff. :D

Thanks for a great piece and for being such a terrific role model.
David, the PDX Fashion Pioneer

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Re: The Wonder of Women's Clothes: My History

Post by JeffB1959 »

I'm happy that so many folks here appreciated my story, my history as a fashion freestyler and that you see me as a role model and inspiration. I take great pride in those compliments and will continue doing my very best to live up to your expectations. Meanwhile, on the bag issue, I started out using this, a Buxton over the shoulder bag/organizer:

Image

As I had said in my initial post, I was self-conscious about using a traditional purse, so I went with the Buxton which I saw as masculine and would work well for my needs. However, I soon got over those insecurities and started using standard women's purses, and I haven't looked back since. By the by, I still have the Buxton which is nice to use as an over the shoulder bag, keeping my hands free, but I also have a couple of women's OTS bags. Like I said, I never leave the house without a purse.
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Wonder of Women's Clothes: My History

Post by moonshadow »

JeffB1959 wrote:I'm happy that so many folks here appreciated my story, my history as a fashion freestyler and that you see me as a role model and inspiration. I take great pride in those compliments and will continue doing my very best to live up to your expectations.
Speaking for myself, my only expectation of you Jeff is to be true to yourself, as you always seem to be. Further, you seem to have a beautiful soul that shines with virtually everything you write and the photo's you post. A beautiful soul is worth more than all the skirts and blouses, and handbags in the world.

Personally, as I know we jokingly tease each other a little about our different styles, it does look good. But the part of you that I admire the most, and try to emulate is your personality. You seem very content and at peace with your life. That's were I want to be. (even if my clothes don't match :lol: )

So keep on keepin on Jeff. I hope I might have the pleasure of meeting you someday and shaking your hand.
-Andrea
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Re: The Wonder of Women's Clothes: My History

Post by Kilty »

Great story, JeffB! I have also just diversified since 2008 myself in that regard, perhaps after admiring former users like Pythos and Veletron who used to look so good in their denim pencil skirts, I took the plunge and bought one myself, went for my first walk in the park as a "bloke in a skirt" but felt something was missing. Sneakers were not ideal so I bought tights and underwear (not anything outrageous, just briefs as I found them more comfortable with the contours of the pencil skirt), some decent boots with a wide heel... I feel more at home in a formal skirt over a casual denim one, but I had to just push myself out there in public rather than hiding, and just dress and go about my business as if its totally normal. I am still taking fashion advice from good members such as SkirtsDad as well :wink:
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Re: The Wonder of Women's Clothes: My History

Post by skirtingtheissue »

JeffB1959 wrote:Time for a confession: I'm a man who loves wearing women's clothes...as a man. Perhaps that makes me a crossdresser or a transvestite, but I don't need to don a wig, put on makeup or strap on a padded bra, just the act of wearing the clothes alone is more than enough of a thrill for me. To wear a skirt or a dress is positively exhilarating; to hear the clicking of high heeled shoes on my feet is intoxicating; and the heft of a full handbag on my shoulder is pleasurable. And the fact that I venture out in public garbed in women's attire from head to toe is exciting in ways I can't possibly describe, and, heaven knows I try, real hard. This is the true extent of my existence as a fashion freestyler, and I love every minute of the experience....
Jeff,
I loved your story, and can identify with several of the feelings you describe. It really sums up the whole Fashion Freestyle bit, as defined by the forum itself as "fashion elements and looks that are traditionally considered somewhat "femme" but are presented in a masculine context." I especially like
I can't help but feel uplifted when I wear these clothes, like they put me on an entirely different plane of existence. I never fail to feel elated when I come and go as I please, dressed how I like without any trouble or negativity...
I know that feeling!

In mid-June a friend of mine and I are going to present a workshop on "Freestyle Fashion" at a naturist event in Pennsylvania (the Eastern Naturist Gathering of the Naturist Society). My friend wears dresses out and about in Philadelphia and I'm a confirmed skirter. I've given workshops on men in skirts but this time we'll discuss feminine-leaning fashion FOR MEN AS MEN. (I would say not crossdressing but don't want to start yet another "yes it's crossdressing, no it isn't" argument!!!!). So, I'd like to read your letter or have it printed as a handout (without your screen name), since it's a very nicely worded account of your experience in freestyling. Is that OK with you? The naturists at the gathering are some of the nicest people I've ever met - it's like one big family of wonderful folks.

Congrats on finding ways to do simple things that give you great pleasure. Thanks for sharing your story!

-----Henry
When I heard about skirting, I jumped in with both feet!
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