JeffB

Cracker

Decidedly repulsive.

Ducks

4 minutes ago, jeremy1986 said:

not at all - not even unmentionables?

Nope, not even that much.

2 hours ago, jeremy1986 said:

@JeffB- that's a great attitude and I applaud you for being so upfront and proud about it.

As you say, not everyone is in the same situation, and certainly not everyone looks as good as you do

If I understand correctly, you don't dress like this ALL this time - its just for occasional excursions, correct? When at home, do you wear anything fem? 

Other than experimenting with outfits to wear on jaunts for an hour or so on certain days when the mood strikes, nope.

Old Navy

Letter

Here's a question: Why would a normal, red blooded, middle aged American male like myself choose to challenge and flaunt the conventions of gender and clothing by traipsing about in public garbed in women's wear? Short answer: Because I like to, plain and simple. These days, I consider it incredibly liberating to cast off the shackles of what I'm expected to look like and present the image that I enjoy instead. Society as a whole demands I dress like a man which, frankly speaking, is dull, boring and usually colorless, that said, it wasn't until I started wearing high heeled shoes as a personal fashion statement that I came to understand that there were alternatives to the staid and dismal essence of men's clothing, and how that would eventually lead to my thumbing my nose at societal norms from a sartorial standpoint.

This form of nose thumbing is what I, and others call “fashion freestyling”, the concerted effort by males, young and old to defy gender expectations when it comes to garments and collectively say, “I'll wear the clothes I want to wear, the clothes I like to wear, and if those clothes come from the women's side of the store, hey, that's how I roll.” And why not? There's no laws on the books that says men can't wear skirts, dresses and high heels, women have worn men's clothes and shoes for decades and no one has said squat, well, the tide has turned to say the least. When I first started wearing heels in public years ago, I had absolutely no idea that would lead to where I'm at today, how I've evolved to where I live for and love wearing women's clothing from head to toe, it's as natural to me as breathing, and yes, I won't deny that I look damn good in a skirt and a pair of heels, a key reason why I enjoy doing what I do as it's intoxicating and at times irresistible. Now, I fully understand that not every man can rock a miniskirt and high heels like I can, nor would I recommend adopting the freestyler’s lifestyle, especially not to the levels I have, but for those who have embraced it, like myself, it's opened up a whole new world where the only limitations on what you want to wear exist in your own mind.

Everyone here knows my personal motto which is my signature, “I don't want to LOOK like a woman, I just want to DRESS like a woman”. I live my motto to the one hundred and ten percent fullest because it is very important to me as a freestyler to look nothing less than my absolute best when out in public, to present a tasteful and presentable image when out in public. I've come to enjoy blurring the lines when it comes to clothing and gender by wearing women's clothes AS A MAN, I feel that's it's vital to question why men have to be so annoyingly limited when it comes to what they can wear while women have no limits whatsoever, something I find to be glaringly unfair. Another reason I've adopted the life of freestyler could be summed up in one word, vanity, the simple fact that I look better in women's clothes than I do in men's, and that I wear skirts and dresses whenever I can because I love how I look in such clothing. I take an enormous amount of pride in being part of a unique fraternity of men who push the envelope by challenging gender norms when it comes to clothing, we boldly pull on skirts, slide our feet into heels and say, “Here we are, world! Deal with it!” And I'm having a hell of a good time as a freestyler.

Henry

heater

Evening

Crawl

Screen

Mutiny

Sweep

I agree with Cali. Style when it comes to shoes means nothing, and I mean NOTHING if they hurt your feet. It's simply not worth the trouble. It would probably be in your best interest to return the shoes and seek a pair that fit properly and not cause discomfort for you.

Good news indeed! Not many places that sell women's shoes in size 13.

Jaunt #388, 8/12/2017: After a slightly soggy start to the day, I headed out on a Saturday jaunt, casually attired in an embroidered turquoise tank top, a short, brown cord pencil skirt I bought at a thrift shop for all of five bucks, the Payless “Parsley” flat sandals in tan and a brown handbag. Thanks to my diligent weight loss regimen, the skirt, which had been a tad snug when I bought it three weeks ago, but now, it fits so well, I didn't need to wear a belt, meanwhile, my passion for flat sandals continues as I've come to really enjoy wearing such shoes, they look so natural on me and I enjoy every chance I get to wear them on outings. Pretty remarkable, seeing that you couldn't pay me to wear sandals a scant few years ago, now, I can't wear them enough.

Anyhoo, since Friday was payday, I decided to take a few dollars to Parx Casino to have a little fun. The place was plenty packed when I arrived, but, no one noticed me, as I've said many times before, casinos are a great place to wear heels or do the freestyle thing because people are too wrapped in their battles with one arm bandits or rolling bones to pay attention to what you happen to be wearing. As it my routine, I always have lunch before I hit the casino floor, busying myself with one cent machines, after about an hour and playing on three or four machines, I managed to win about $70 bucks. WHOO! Windfall! Gotta love it! After another half hour of fiddling around, I left with my meager winnings and motored down the expressway to an outlet mall a mile away where I went to its multiplex to watch Atomic Blonde which was a cracking good action flick, starring Charlize Theron as a kick ass British secret agent during the last days of the Cold War and the fall of the Berlin Wall. Oh yeah, she also wore some awesome heels as well!

After the movie, I wandered through the mall which had a good Saturday afternoon crowd, I did get a few stares here and there, but nothing more than that, I wandered in and out of a few stores, but didn't find anything that interested me. Meanwhile, going to casinos on outings continue to be fun, maybe I'll go to Atlantic City on a future outing. More to come....

8 hours ago, OldMountain said:

Jeff B;

looked into Flickr? 1 tb of storage, not bad. Thats soo many photos its unbelivable. 

Oh, I have other options, but I keep hoping against hope the folks at Photobucket will come to their senses and lower their "ransom" price for third party hosting to something much more reasonable. If that cost was say, $100 a year, I could live with that. $400 is flat out insane.

I see, said the blind man! Most interesting! Meanwhile, Eddie is awesome!

On 8/7/2017 at 10:03 AM, SkirtDude said:

I love the earrings! Can't wait to see your printed skirt. I've just been shopping and bought two more pencil skirts for work, one in lilac which I might wear with a similar colored blouse (though am at a loss as to what color tights I should wear), booties (summer has gone abroad in the UK  ) and might treat myself to a new bag. The other skirt was a gray one with a check design, but not plaid.

I like your top as well. Did you pierce your ears or are those clip-on earrings?  

To answer your question, those were clip-on earrings. I'm not quite ready for piercing, but I'm thinking that will happen eventually.

4 hours ago, HappyinHeels said:

SkirtDude,

I'm a bit confused on something. Who is the guy in a dress and sandals in front of an NBC (Channel 4) affiliate? THey don't have NBC in Great Britain but a Brit is posting it. Were you just over here in the USA and saw this where you were staying?? I'm not sure what the news story was exactly. The guy looks like he would blend into most urban landscapes as he seems passable. Thoughts?   HappyinHeels

I'm afraid you've lost me. Could you provide more information?

Jaunt #387, 8/6/2017: On the heels of Saturday's outing, I decided to head out for a second straight day, mainly because I had the itch to go out in a skirt, and since the weather was nice, so, why not? As for the ensemble, it was a combination of casual and dressy, or casually dressy as I sported a blue “Swiss Dot” t-shirt (see picture below), a black denim pencil skirt, the Payless “Parsley” flat sandals in black and a black handbag. While I could've made this outfit dressier by adding a pair of heels, that never occurred to me as I was eager to wear sandals which had became something of a passion for me this summer season, but it still looked more than good enough for a day out in public.

My destination was South Jersey, Moorestown Mall where I hadn't been to for awhile, but first was lunch at Wendy’s where I had a nice salad (still vigilantly watching what I eat) and a bottle of water. Then it was off to the nearby multiplex to catch a showing of The Dark Tower starring Idris Elba and Matthew McConahgey which was pretty darn good, in fact, it makes me want to read Stephen King’s original novel which the movie was based on. After the movie, I decided to do a little shopping in the nearby Sears where I enjoyed wandering the aisles of women's wear before heading to the counter with not one, not two, not three, but FOUR casual dresses, and I only spent a tad over $35 bucks for the haul. Not bad at all. From there, I swung by the Cherry Hill Mall where I hit JCPenney and did some more shopping, coming away with a nice dressy blouse and an equally nice printed knee length skirt to pair as an outfit I thought up on the fly after looking around the aisles.

I have to say I felt plenty good as I drove home with my stash of clothing, adding more dresses to my closet, all of which I plan to wear on future outings, of that, you can be sure, and it'll be fun, because that's what wearing a dress is all about. Oh yeah, no one cared about what I wore today, but then, no one does, and that's plenty cool. More to come....

8 hours ago, jeremy1986 said:

Lovely skirt, @JeffB - and the sandals match is beautifully.

Well done on 300 jaunts!!! 

2 hours ago, SkirtDude said:

Looking great as ever, Jeff! Nice to see a selfie outside, though it would be nice to see a whole shot of your ensemble whilst on your jaunt! Nice skirt  

Thanks for the kind words!

Jaunt #386, 8/5/2017: You'd think that as much as I love numbers when it comes to my thread, I would've known that this outing was my 300th in a skirt, but I wasn't aware of that until I returned home and entered the stats for the jaunt. In a word….WHOA! To think I've worn skirts THAT many times now has been astonishing, but, more importantly, it's been a hell of a lot of fun, and it continues being an absolute blast. Anyhoo, I found it appropriate that my 300th jaunt in a skirt was to the King of Prussia Mall, a place I would NEVER have thought about venturing to just a year ago, but now has been commonplace when it comes to destinations to enjoy a day of freestyling.

Anyhoo, regarding today's ensemble, I sported a turquoise blouse with a tan chino pencil skirt, the Payless “Stacia” low wedge sandals in tan and a beige satchel bag. I arrived at the mall garage shortly after 11 a.m., hopped out and went into the mall. I remember experiencing a measure or nervousness the first time I wore a skirt at KOP, wondering how my appearance would be received, and when nothing of substance happened, despite being around thousands of people at the largest mall on the east coast, I came to realize that what I was wearing had no impact whatsoever with the people there, and on my ninth trip there in freestyle mode, nothing at all has changed, and I find that refreshing. Being a creature of routine, my first stop was to the comic book shop there where I spent a good fifteen minutes or so, then I sauntered down to the food court which was mildly crowded for lunch. I stood in line at Chick Fil A where I bought a chicken salad sandwich and a bottle of water, then sat next to a large and rather boisterous family, intentionally to enjoy my meal, and without nary a notice from the family, in fact, the only time those folks took notice of me was when the mother, looking a tad frazzled, apologized for her kids being noisy, I grinned and told her it was no problem.

After lunch, I wandered about, passing by the now shuttered store that used to be JCPenney, I felt down since I bought several skirts, women's tops and handbags there. My wandering through the mall, passing scores of uninterested people led me into Old Navy on a whim, and, on another whim, I wound up buying a couple of dresses that caught my eye because they were cute and casual and interested me. I'll be sure to show them off on future adventures. And so, with my 300th skirt outing in the books, having spent little over fours at KOP, I'm looking forward to many, many more outings there in the future. More to come....

12 hours ago, jeremy1986 said:

What a stunning dress, @JeffB - looks so naturally femme on you!

Thanks for the kind words. I'll say this, I certainly felt feminine while wearing that dress. And that was a good feeling to have.

8 hours ago, Bubba136 said:

Jeff B is one of these rare individuals that looks like a man when he dresses like a man and a woman when dressed like a woman.  Wonderful trait wnen you think about it.  :-)

Well, you're not the first person on this board who came right out and said I look like a woman when I'm dressed like one. Perhaps that explains why I never get any strange looks while out in public because I'm accepted as a woman thanks to my appearance. I appreciate the compliment, and yeah, that is quite a wonderful talent to have.