The Man in the Dress

[JeffB]

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.

[SF]

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

[JeffB]

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.

[Cali]

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 June 25, 2019 by Cali

[HappyinHeels]

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  HinH

[p1ng74]

And to think, some people pay $2600 to be just as fashion forward:

https://www.gucci.com/us/en/pr/men/ready-to-wear-for-men/shirts-for-men/tartan-cotton-long-smock-shirt-p-632536ZAFDL7261

 

 

[RonC]

 

After clicking on the link, I thought to look at men's shoes to see if heels were being offered for men.  No heels, but the following two styles appear in the "what's new" section specifically for men.  Interesting.

 

 

[nzfreestyler]

12 hours ago, RonC said:

 

After clicking on the link, I thought to look at men's shoes to see if heels were being offered for men.  No heels, but the following two styles appear in the "what's new" section specifically for men.  Interesting.

 

 

looking around that site - these are more my style... not too weird looking but still pretty. I don't think I could do those 'mens' new styles.

cheers

NZF

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[JeffB]

5 hours ago, nzfreestyler said:

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looking around that site - these are more my style... not too weird looking but still pretty. I don't think I could do those 'mens' new styles.

cheers

NZF

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VERY nice, though I doubt they come in battleship (13 wide) size!

[nzfreestyler]

I think Gucci goes to 41 EU only in womens heels  - I think that is like a US 9/10 ?

[RonC]

12 hours ago, nzfreestyler said:

looking around that site - these are more my style... not too weird looking but still pretty. I don't think I could do those 'mens' new styles.

I agree wholeheartedly.  I was just surprised to see what to me was a very fem style in the men's section of a mainstream, high end retailer.  I'd much rather these myself!

 

[jeremy1986]

On 9/29/2020 at 10:36 PM, p1ng74 said:

And to think, some people pay $2600 to be just as fashion forward:

https://www.gucci.com/us/en/pr/men/ready-to-wear-for-men/shirts-for-men/tartan-cotton-long-smock-shirt-p-632536ZAFDL7261

 

 

Did they intentionally get a male model that looks like a woman to model clothes to "disrupting the toxic stereotypes that mold masculine gender identity"??

[mlroseplant]

On 10/1/2020 at 10:59 AM, jeremy1986 said:

Did they intentionally get a male model that looks like a woman to model clothes to "disrupting the toxic stereotypes that mold masculine gender identity"??

I don't think the dude looks anything like a woman. Yeah, he's skinny, but that's a model thing, yeah? On a different point, I cannot possibly imagine how anyone can justify either buying or selling a shirt/dress for 2,600 USD. I mean, they put that price point out there, and SOMEBODY must be buying this stuff.  Who? I want to find out, so's I can slap them silly. You could have something custom made for a fraction of that price.

[JeffB]

On 10/1/2020 at 11:59 AM, jeremy1986 said:

Did they intentionally get a male model that looks like a woman to model clothes to "disrupting the toxic stereotypes that mold masculine gender identity"??

Never mind disrupting toxic stereotypes, yadda yadda yadda, $2,600 for THAT piece of crap? Seriously? I’ve seen better looking dresses at Wal-Mart! It probably cost all of ten or fifteen bucks to sew that thing in some sweatshop while the Gucci tag represented the rest of the cost. Hard pass!

[p1ng74]

I think it is a nice piece, and I think I would be challenged to find something like that at Wal-Mart.  Wal-Mart clothes are usually slapped together with no attention to detail.  On this piece, the lines on the pattern of all the fabric pieces line up nicely, etc.  But yes, a good tailor can also put this together for a fraction of $2600.  

[Cali]

5 hours ago, p1ng74 said:

I think it is a nice piece, and I think I would be challenged to find something like that at Wal-Mart.  Wal-Mart clothes are usually slapped together with no attention to detail.  On this piece, the lines on the pattern of all the fabric pieces line up nicely, etc.  But yes, a good tailor can also put this together for a fraction of $2600.  

But why would you?

[p1ng74]

On 10/7/2020 at 5:29 PM, Cali said:

But why would you?

You don't think I would look cute in that Gucci dress? 

I did enjoy wearing this today, and it didn't cost $2600:

[Cali]

1 hour ago, p1ng74 said:

You don't think I would look cute in that Gucci dress? 

I did enjoy wearing this today, and it didn't cost $2600:

Whether you look cute or not is not for me to decide, that's for your wife to say, but I don't think she would say you would good.

Or anybody in that "outfit".

[CAT]

  On 6/25/2019 at 3:50 AM, 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.

 

Just saw this post from JeffB,,,Guess I fall into the colossal balls catogory too!!! LOL  It is reall not that hard to do once you do it 1 time you can't get enough!

 

[pebblesf]

I remember all those great pictures...

[spikesmike]

CAT : Personal question. You are out and about wearing the above outfits (Looks Great) where all the people around you can see your face . So, Why is your face cutoff in the above photos ?  spikesmike

[RonC]

Nice to see some pics again from you CAT.  You make Chicago look better....lol

 

[Pierre1961]

Fantastic pictures! 

Yes it for sure takes a lot of courage and self confidence for wearing these outfits. 

And master the high perfectly. 

I admire you! 

Pierre 

[HappyinHeels]

many of these look like previously posted photos but all of them could be worthy of leg contest submission. CAT really knows how to rock the heels and the outfit. HinH

[jeremy1986]

On 10/9/2020 at 2:34 PM, pebblesf said:

I remember all those great pictures...

Same. @CAT has always rocked these looks....

[CAT]

On 10/9/2020 at 9:02 AM, spikesmike said:

CAT : Personal question. You are out and about wearing the above outfits (Looks Great) where all the people around you can see your face . So, Why is your face cutoff in the above photos ?  spikesmike

 

Great  question  Spikesmike!   The simple answer is my kids.  Although they completely know and have seen my apparel I do not wear these types of outfits around my home town.  As we are all accepting of others on this site I would not have my kids be put in a bad situation due to my clothing choices.   I do however wear leggings and boots and there have been some comments. They would definitely get grilled for a skirt and heels.   I do leave my house dressed and head to the city but there is always a chance of running into someone from home, but that has not happened in 7 years.   So blocking or cropping out the head in the pics is just to protect my kids from any harassment as anything can be found on the internet.   A while ago I left my house dressed up stopped at the dentist and then met Pebblesf for dinner in the city and had  a great evening. 
 

[pebblesf]

8 minutes ago, CAT said:

On 10/9/2020 at 10:02 AM, spikesmike said:

CAT : Personal question. You are out and about wearing the above outfits (Looks Great) where all the people around you can see your face . So, Why is your face cutoff in the above photos ?  spikesmike

 

Great  question  Spikesmike!   The simple answer is my kids.  Although they completely know and have seen my apparel I do not wear these types of outfits around my home town.  As we are all accepting of others on this site I would not have my kids be put in a bad situation due to my clothing choices.   I do however wear leggings and boots and there have been some comments. They would definitely get grilled for a skirt and heels.   I do leave my house dressed and head to the city but there is always a chance of running into someone from home, but that has not happened in 7 years.   So blocking or cropping out the head in the pics is just to protect my kids from any harassment as anything can be found on the internet.   A while ago I left my house dressed up stopped at the dentist and then met Pebblesf for dinner in the city and had  a great evening. 
 

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And I had a great time indeed, and plenty of encouragement...  Sure hope we can do it again when things calm down...  Don

[CAT]

We will when everything calms down!!!

 

[spikesmike]

pebblest & CAT : As I recall you are from the windy city. I don't like to invite myself to a party but would love to meet up with you guys for high heel meet.

[CAT]

I know we have tried in the past to do a meet up in Chicago and schedules just did not match up,  I think we should be able to set something up ands see who is available!!!!