The Wonder of Women's Clothes

[JeffB]

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.

As everyone here knows from my years as a member of this board, my special journey started 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 and hopelessly static 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 jaunting routine, they looked good on me, and I desired to wear them more, going with various lengths, 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 quite 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 sartorial passion that was welling up inside me, and I wasn't about to stop.

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 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, and I've said this more than a few times, I don't feel dressed without a purse.

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 blazer and a pair of 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. 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, and letting the world see me in them. And the feeling is wonderful!

Edited May 28, 2016 by JeffB

[Heelster]

----and you do this so well.

[Thighbootguy]

JeffB has provided us with an insightful description into his adventure in discovering nontraditional attire  for a male.  The phrase "women's clothing" describes a categorization of articles normally worn by the female of our species  and what JeffB has done shatters that categorization with which most have become comfortable.  This is what makes some people uncomfortable.  Go JeffB!

What makes JeffB clothing selection significant is that he isn't just wearing "women's clothes", rather he is wearing "his clothes", and the fact that he does it well cannot be discounted.  This goes back to a comment someone made on this board years ago when asked if he was wearing women's shoes, and he replied, "No, I'm wearing my shoes".

[JeffB]

Thanks for the kind words. My evolution as a fashion freestyler has made wearing women's clothing a great deal of fun as I've gone to great, almost obsessive pains to look the very best I can when out in public. And yes, when I am out and about, I'm wearing MY clothes, they just so happen to come from the women's side of the store. To openly challenge society's conception about what men are allowed to wear has been most fulfilling, when people see me, I want to force them into the realization that not only don't I look odd or freakish in the clothes I choose to wear, but that I look good in them as well. Proper and tasteful presentation is EVERYTHING to me, and if I can display to the world at large that men CAN look good in skirts and heels if done correctly. And that's a mission I undertake to the very best of my ability with each and every outing.

[robbiehhw]

You do an excellent job and your outfits and style continue to evolve in an inspiring way. Thanks for sharing it all with this community. Technically anyone that puts on a pair of panties or a pair of heels is a crossdressing. Same with a woman that likes men's jeans.  Labels are just labels though and the important thing to do is be true to yourself and enjoy it. You seem to be doing both

If i could nitpick regarding one label - "Transvestite" is no longer a loved term in the Transgender community. (it sort of goes with terms like shemale etc) Now it is just transgender. Many, if not most crossdressers are not transgender although they are thought as of being on the gender variant continuum because you are presenting yourself in a way that that is traditionally associated with one gender. Other folks in that category include genderfluid, agender, non-binary etc. 

Keep up the great work!

[HappyinHeels]

JeffB,

You have been a consistent source of articulate advice and "Philadelicious" fashion photos describing your amazing 8-year journey. I love the clothes like you do. The shoes are the draw but I adore the dresses and skirts, the handbags, the polished nails, the jewelry, the lovely dress watches, and the artistry of the hair and makeup. It does take a lot of time! Most guys here will figure out what their niche is: maybe just a few heels, a few accesssories, or the whole feminine package. Who doesn't like the extra ventilation on a warm day? The sheer array of colors and fabrics makes womens clothes more appealing to the eye and consequently makes everyone who sees it feel more positive about the world around them. A wedge sandal of 5-6" with polished toes and a cumfy pair of jeans will make your heart sing indeed. If just 10% more of the of the biological male population acted on the desire to get in touch with their X chromosomes the world would inevitably be a more peaceful place. It has nothing to do with sexual preference and everything to do with existential preference.   HappyinHeels

[Bubba136]

I, for one, have been a long time (years) member of the JeffB fan club.

[JeffB]

This past Saturday, I bought a cute Liz Claiborne top and skirt set, both in light gray from JCPenney, and when I tried it on back home with a pair of black patent pumps (the Payless "Karmen" shoes), I was suitably impressed with how nice I looked, and that brought to light yet another paradigm shift in my ongoing evolution as a fashion freestyler: I look better as a guy in women's clothes than I do in men's clothes. I've made no secret of the fact that I can work a short, tight skirt and a pair of stiletto heels just as effectively as any woman, in some cases, better, and I'm proud of that admission. Few things in life makes me happier than when I'm strutting my stuff in a skirt or dress because I love wearing them, and, more importantly, I look damn good in them. I can only assume that I'm fortunate to be thin in stature, and my height also lends an air of style to the clothes I wear, plus the fact I go above and beyond to look nothing short than my very best when out and about, and that means everything to me. I've come to realize how women's clothes suits me in ways men's clothes don't, that I look better in a skirt of any length, color, fabric and style than dull and boring men's pants, and that knowledge is certainly intoxicating in ways I can't describe. I plan to continue strutting my stuff and looking my best in the clothes I choose to wear, and love to wear.

[Thighbootguy]

2 hours ago, JeffB said:

: I look better as a guy in women's clothes than I do in men's clothes.

Beauty is in the eye of the beholder.  It really is a matter of how we see ourselves. Some folks (male and female) like their look when wearing a tailored three piece suit, some folks really like their look wearing jeans. Some folks like to project a masculine look and others like to project a more feminine look.  The look we project is generally a reflection of what is inside the clothing and I am thankful that I live in a place and time that lets me make that projection.

I am within days of progressing from being a being sexagenarian to becoming a septuagenarian so I offer this quote:

"Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did. So throw off the bowlines, sail away from the safe harbor, catch the trade winds in your sails. Explore. Dream. Discover."

~ Mark Twain

 

[Bubba136]

I'll drink to that!

[JeffB]

On 8/26/2016 at 9:49 AM, Thighbootguy said:

Beauty is in the eye of the beholder.  It really is a matter of how we see ourselves. Some folks (male and female) like their look when wearing a tailored three piece suit, some folks really like their look wearing jeans. Some folks like to project a masculine look and others like to project a more feminine look.  The look we project is generally a reflection of what is inside the clothing and I am thankful that I live in a place and time that lets me make that projection.

Well, I'm proud to say I enjoy presenting a purely feminine look when on my outings. When I look pretty, I feel pretty, and it's a wonderful experience, I wouldn't have it any other way.

[JeffB]

Now that September has arrived, summer will be winding down and fall will be on the way, that will mean changing my attire for the upcoming season. Deciding just when to stop wearing white clothes and shoes after Labor Day has gone; breaking out my long sleeves tops and jackets; swapping out my light fabric skirts for heavier fabrics; switching my slides and sandals in favor of pumps and boots. For sure warm weather will be around for awhile, at least for most of this month, but, as temperatures gradually cool, it'll be important for me to be prepared in terms of clothing and footwear for the season to come. For sure I'll be observing women as to what they'll be wearing and jotting down ideas for what will work for me in terms of fall attire.

[robbiehhw]

I love the transition to fall. Ankle boots and boots come out. scarves, sweaters, leather jackets as well. 

[Thighbootguy]

1 hour ago, robbiehhw said:

I love the transition to fall. Ankle boots and boots come out. scarves, sweaters, leather jackets as well. 

Yep   Really looking forward to it.

[flavio]

Love to know that your taste for good clothes is evolving my friend, there's a lot of time I don't come here and when I decide, gosh, JeffB is always around with his good taste and sensational support to everyone.

I'd like to say that I'm also on the "girls" clothes stuff and started wearing pieces of their wardrobe recently around selected places.

Freedom of expression to everyone, kudos to JeffB!

[JeffB]

Thanks for the kind words, flavio! Much appreciated! Freedom of expression is indeed important!

[KneeBooted]

I want to add a +1 to this thread. Aside from my heels, a friend of mine when I was younger convinced me to get into wearing women’s jeans to help my lower half look better. I hated the way men’s stuff always looked so baggy and if I wanted well fitting pants/jeans, I would need to spend in upwards of $80.

She worked at GAP at the time and helped me find a couple of pairs that looked good, fit well, and amazingly comfortable. I admit that for some reason until that day, I never thought about women’s jeans being more comfortable.

Fast forward well over 10 years, and now all of my clothing from the waist down is women’s. I won’t go into detail, but I finally gave up wearing boxers to work because they just bunched up in my jeans.

Now that I’ve been out in California for a bit, I’ve started letting my mind wonder about with regard to women’s tops too. I did have those thoughts previously but I usually just let them go, because I was living in a conservative judging area and around some family that didn’t even really know about my heels.

The down side though is trying to find good fitting tops. I say it is easier to find bottoms, but it seems there are so many shapes and sizes of tops that I have to venture all over the place. But I won’t let that stop me though. Thanks to @JeffB and your multitude of fashionable posts, I am convinced I will find some that suit me!

[Cali]

About 70% of what I normally wear started as Women's. I find better, tighter fit (form fitting-not bulky), and more colors and choices. I'm between Medium and Large in men's, so many times the medium is just too small and the Large has soooooo much extra material that I could swim in them. It's easier to layer when your clothes are not so bulky and it is easier to do many athletic things with less bulk. Besides, I'm fit for my age and I want to show it off.

You wouldn't believe how many men and women have complimented me on my Victoria's Secret sweater (aka jumper). I don't dress to look feminine, I dress to look good.

Edited January 20, 2019 by Cali

[CAT]

 

 I don't dress to look feminine, I dress to look good.

Well said  Cali !!

I use “ I’m not here for a long time,,,, I’m here for a good time!!”

[Cali]

I just purchased (on-line) a new top from Express in thornberry. Never heard of the color thornberry before tonight.

Edited January 20, 2019 by Cali

[JeffB]

10 hours ago, KneeBooted said:

The down side though is trying to find good fitting tops. I say it is easier to find bottoms, but it seems there are so many shapes and sizes of tops that I have to venture all over the place. But I won’t let that stop me though. Thanks to @JeffB and your multitude of fashionable posts, I am convinced I will find some that suit me!

I've found that shopping for women's tops can be a tad problematical. If you're tall and have long arms like me, sleeves often fall short which isn't a good look. Since men tend to be a bit thicker around the chest than women, you'd have to buy one size larger than needed. What helps is to take measurements of your chest, then check the sizing charts for women's tops and see what size works best for you. Good luck with your search.

[HappyinHeels]

I don't have many women's style tops but always have to remember to moisturize my arms and elbows lest they take away from the look of the top. I highly recommend that KneeBooted consider wearing women's style tops in California. The mild weather lends itself to wearing such tops and the array of choices is mind-boggling. SF has a extraordinary number of thrift shops. HinH

[Gudulitooo]

JeffB,

The only thing you miss is the limited budget many women face. How would you deal with that?

[JeffB]

On 1/22/2019 at 4:35 AM, Gudulitooo said:

JeffB,

The only thing you miss is the limited budget many women face. How would you deal with that?

Well, I'm far from wealthy, so I'm careful when I shop, favoring places with sensible (read: low) prices like Sears, JCPenney, Old Navy, Primark and Payless, and I always look for bargains wherever and whenever I can.

Edited February 10, 2019 by JeffB

[alphax]

On 1/20/2019 at 2:19 AM, JeffB said:

I've found that shopping for women's tops can be a tad problematical. If you're tall and have long arms like me, sleeves often fall short which isn't a good look. Since men tend to be a bit thicker around the chest than women, you'd have to buy one size larger than needed. What helps is to take measurements of your chest, then check the sizing charts for women's tops and see what size works best for you. Good luck with your search.

Mens’ arms are longer in proportion than womens’. Mens shoulders are also wider in proportion.

For the rare occasion that I need long sleeved garments, I turn to stores or sites that specialize in womens tall sizes, to buy jackets and long sleeved tops.  These same places will often have larger sizes that are just right for my US size 18/1X shoulders. 

When I buy sleeveless, short, or 3/4 sleeved, I just go with regular womens’ sizes.

For bottoms, I just buy regular womens’ sizes.

[Pierre1961]

Have you ever tried " Long tall Sally"?

[Cali]

Men's torsos are also longer. I look for and buy styles that come in "Tall". I'm medium is both men's and women's, wear US size 8 and 10. Sometimes I will get a large if I am going to layer them and the item is to be on top.

[HappyinHeels]

I am a medium build and only 5'8" (174cm) tall and do not have the standard longer arms, bigger feet (sz 10-11 US), or bigger hands. People tell me I have a powerful grip, I think it's heriditary, but my hands are not large. I find by wearing a waist cincher, or corset if you're going somewhere fancy, that makes the top seem to look better. I can shop for a sz16 top (misses or womens) or a sz 14-16 in a dress and have a great fit every time. I find pants shopping more challenging because of my short inseam at just 30"(76cm). I have to consider if the pants are likely to be worn with heels or not and how they fit my midsection. I know we have quite a range of builds among our members. HappyinHeels

[alphax]

On 2/11/2019 at 8:59 PM, Cali said:

Men's torsos are also longer. I look for and buy styles that come in "Tall". I'm medium is both men's and women's, wear US size 8 and 10. Sometimes I will get a large if I am going to layer them and the item is to be on top.

That's true that men's torsos are longer.  The way I was taught to compensate for that and present correct body proportions, was wearing the waist on skirts about 2 inches above my belly button.

[KneeBooted]

Well, I can officially say that I have my first top for everyday wear that wasn’t purchased from the men’s section! Recently my wife and I had gone out shopping and I had been on the lookout for a new jacket.

That still eludes me, but we ended up in Old Navy looking for stuff for her. In the back of my mind, this thread has been stirring. Mainly I have been envious that there are so many cute options for women and not much marketed to men.

Well my wife had tried on a shirt that she didn’t like on her, but I mentioned that it might look good on me. She agreed and I went and picked a couple of larger sizes out. Sure enough, a woman’s large fit quite well! It’s a “football style” shirt with some stripes on it.

Now it is not the first top I’ve bought out of a woman’s section. I did that around Christmas at Kohl’s when I got my sweater that said either Naughty or Nice on it. It is though the first one I will wear out on a regular basis. Nothing like entering into an exciting arena!