JeffB Posted January 1, 2015 Share Posted January 1, 2015 When I first became a member of this board, and began my rather unique journey, I was just a simple heeler, perfectly content in the beginning to just wear women’s shoes under long jeans, nothing more, nothing less. Then, I began evolving, discovering the joys of wearing nicer clothes that complimented the shoes I sported, then came skirts, first as an experiment, an exploration fueled by curiosity, but when I discovered that I looked good in skirts and enjoyed wearing them, they became part of my fashion equation. Then in May of 2013, I indulged in another experiment, wearing skirts exclusively for the rest of that year, when 2014 rolled around, my love for skirts had grown so large, I ditched all my pants and jeans to wear skirts full time on my outings. And now, the next stage in my evolution as a fashion freestyler----dresses. The first time I wore a dress, a sleeveless black sheath which I paired with a blazer and a pair of pumps, I felt a particular sort of energy, electricity perhaps, there was no denying that I looked good in the dress (I wouldn't have worn it if I didn't), and, more importantly, I felt good wearing it, even more telling was that I experienced no nervousness or anxiety when I ventured out in my outfit, like it was no big deal to be seen in public wearing a dress, in fact, I felt proud to wear it. I've worn dresses three times since then, and each time, I felt just as comfortable, at ease and, well, happy, on top of that, I've also felt an...eagerness to wear dresses more. It takes a special sort of boldness and confidence to wear a dress, seen as the ultimate women's garment, the dynamics of a man wearing a dress in public as a man, no wig, no makeup, no false breasts makes for an exceptional challenge, and a fun challenge. Like I said, this figures to be the next stage in my development from those far off days when I hid heels under long jeans, now I'm proudly, and publicly wearing women’s clothes from head to toe, living up to my personal philosophy which everyone can see in my signature: “I don't want to LOOK like a woman, I just want to DRESS like a woman”. And wearing dresses have slowly become part of that equation, it's just a fantastic garment that fits who I am, and my identity as a fashion freestyler, and I'm excited for the chance to wear them more frequently. In fact, I've already started planning for just what sort of dresses I want to wear, and what kind would look best on me, both now in the cold of winter, but for spring and summer. Sweater dresses, shirt dresses, tank dresses, little black dresses, jacket dresses (I have two), maxi dresses, maybe even a bodycon (I'm just crazy enough to try one) or a sundress, I'm willing, and eager to experiment with just about anything. I find the dynamic nature of dresses increasingly irresistible, and I want to explore them, just like I had with skirts once upon a time. While there's no way to know what the future holds, I wouldn't be at all surprised if, several years down the road, I'm wearing dresses full time on my jaunts, that would simply be part of my ongoing devotion to fashion freestyling. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
LovesHiHeels Posted January 1, 2015 Share Posted January 1, 2015 Good story. I used to just wear dresses around the house when I was on my own but now wear skirts as well. Easy wearing skirts but dresses take a lot more thought in buying the right dress to fit a man well.. I find tight or Bodycon dresses work well. I,mI having to return a lot more dresses then I do skirts. Link to comment Share on other sites More sharing options...
JeffB Posted January 3, 2015 Author Share Posted January 3, 2015 Good story. I used to just wear dresses around the house when I was on my own but now wear skirts as well. Easy wearing skirts but dresses take a lot more thought in buying the right dress to fit a man well.. I find tight or Bodycon dresses work well. I,mI having to return a lot more dresses then I do skirts. Agreed, it's not easy to pick a dress that will fit a man well, but I think I've done well with what I've worn so far. As for bodycon dresses, they would present the biggest challenge, and I would look forward to wearing one in public. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Oxford1 Posted January 3, 2015 Share Posted January 3, 2015 It is hard to find a skirt that fits right,finding a dress is even harder. You just cannot beat the comfort of both. the Mideast people are way ahead of us. Seems women have this love/hate relationship with heels and dresses. Don't now why as they are both so beautiful! Link to comment Share on other sites More sharing options...
Aly Posted January 6, 2015 Share Posted January 6, 2015 I discovered sundresses last year - you're covered up but feel like you're not wearing anything! The fabrics are very light and airy and they feel great! Wealth is not measured by how much you have, but rather how little you need. Link to comment Share on other sites More sharing options...
SleekHeels Posted January 7, 2015 Share Posted January 7, 2015 On the whole I tend to prefer skirt and top combinations because I wear tops one size bigger than my skirt size so it's easier to get a good fit. With dresses I usually have to buy according to my top size so I sometimes end up with the bottom half of the dress being a bit too big or loose. That's not too much of a problem with more floaty styles, and even with bodycon dresses the stretch of the fabric sometimes compensates quite well and fits easier than some more structured tailored styles might. The first couple of dresses I bought looked nice on the shop mannequin but not on me, but these days I always try them on in store and only buy the ones that feel like a good fit and look flattering (in my own mind's eye at least). Dresses have to accommodate all sorts of sizes and shapes of customer, so it's just a case of trying lots to find the few that work well. Women have just as much difficulty finding the right dress, so guys shouldn't expect it to be any easier. I own around ten dresses. In terms of length they vary from mini to midi, mostly bodycon but a couple of the longer ones are a bit more floaty. I almost always wear some kind of top with the dress, either a smart blazer, a more casual jacket (leather or denim), or a smart cardigan, and that opens up more possibilities for wearing sleeveless strappy styles (which makes fit on the shoulders and arms far less of an issue). About half of my dresses are day dresses, either plain or some kind of floral or geometric pattern, while the other half are more party-style dresses that I'd only dream of wearing on a special occasion (but have occasionally combined with a casual jacket for a slighly more everyday smart look). Finally, I do feel equally comfortable wearing a dress, skirt or trousers (all with heels of course) but I do sometimes feel that the dress or skirt makes it easier for people to "dismiss" the concept of guys in heels because they just assume that I want to be a woman. So while wearing a dress is exciting and fun, I do also enjoy wearing my heels with trousers because I feel that makes more of the statement that I want to make. Jeff, I'm sure you'll have a lot of success and fun incorporating dresses into your repetoire, and I hope it will inspire other guys who would really like to try a dress but don't believe that a guy could ever make it work. If you like it, wear it. Link to comment Share on other sites More sharing options...
JeffB Posted January 11, 2015 Author Share Posted January 11, 2015 SleekHeels: Thanks for your insightful comments, they certainly made for good reading, and even gave me a few fashion ideas as to how to move forward in my growing interest in wearing dresses. I agree wholeheartedly that whether you're a man or a woman, it is indeed a considerable challenge to find just the right dress that both fits well and, more importantly, looks good, taking into account for body type and height and the sort of style you want to wear. It's vital to critique yourself and arrive at a decision as to what sort of dress would work best. And, of course, you have to FEEL comfortable wearing a dress as well. The first dress I bought (and still have) was my black, sleeveless sheath which I paired with a gray blazer and plain black pumps, presenting a smart, stylish look that could take me from busy downtown locales to quiet suburban restaurants. I've come to think I present a nice image when wearing close fitting dresses like sheaths and the sweater dress I sported on my 250th jaunt, that's what led me to thinking I could make a bodycon work and not embarrass myself in it while in public. And while I've been partial to solid colors, I've also looked nice in a pattered jacket dress I sported on another outing. However, I want to experiment with other styles, including A-lines and maxidresses and various fabrics like denim, cotton and knits. There are many options when it comes to dresses, and I'm eager to explore as much of them as I can. SleekHeels is right, if you do enough research and experimentation, I believe it is possible for a man to look good in a dress. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
robbiehhw Posted January 27, 2015 Share Posted January 27, 2015 My own dress and skirt wearing has continued to increase over the last decade. In that time, I've become more feminine. There was a time wear i felt totally fine in girl jeans, heels and a top but felt self conscious in a skirt or dress. I wear sheath dresses, maxis, and wraps. I try to dress my age and not get too high with the hemline and dress in colors that are complimentary. Still, i end up only wearing dresses or skirts a few days a month. I really don't have any good reason for that. Link to comment Share on other sites More sharing options...
Guest Posted January 29, 2015 Share Posted January 29, 2015 This is what scares my wife. She is afraid of at what point will it stop. There is no way that I would ever look "good" in a skirt. Not because of that, I have assured her it will go no further than where it is now. I wear heels every day, woman's jeans and mostly hose. Even if I wore no other woman's clothing I would still wear the jeans just because I really love the fit. I like the mid rise jeans so the crotch is not hanging to my knees and I really like the material. My wife likes them because since they are no baggy in the rear she likes my hinney. Link to comment Share on other sites More sharing options...
HappyinHeels Posted February 7, 2015 Share Posted February 7, 2015 JeffB, I adore dresses and always have. I have just two skirts but 14 dresses, all just above the knee to about 5" above the knee. Some are sleeveless, some have a typical 4-5" sleeve, and the rest have 3/4 sleeves which hide my elbows but jewelry like bracelets and dress watches to be seen. The type of typical spring dress worn with wedges or pumps also works as a great sleep garment. The material is naturally soft and I sleep very well. Every now and then I have a chance to go to some occasion and go out with a great dress, big hoop earrings, eyeshadow, lipstick, foundation, thigh high pantyhose, long acrylic nails, and sky-high heels (never under 6") and a shoulder-length wig. I am not shy but rarely get the chance to share the experience. My wife likes my heels and dresses when she is in the mood which is when either college-age kid is not at home. When we both go up to our 40 acres in far northern Wisconsin then I always take my dresses and heels. In the meantime I enjoy shoppng and going places as a hybrid: No wig or makeup, maybe a handbag or not, bootcut androgynous jeans, sweater or turtleneck sweater top, and heels be they high wedges, pumps, or boots. I don't paint my fingernails daily but do wear a woman's dress watch and go about my business with no issues at all. Keep evolving Jeff it's what makes you special. HappyinHeels Link to comment Share on other sites More sharing options...
JeffB Posted February 8, 2015 Author Share Posted February 8, 2015 Thanks for the comments, everyone! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
JeffB Posted January 26, 2016 Author Share Posted January 26, 2016 After my most recent outing where I wore a black sweater dress, I remarked about how much I enjoyed the experience, and, ever since then, I've been thinking about wearing dresses more and more because they're just awesome. Just like skirts, dresses suit me and my personal sense of style. I can't wait to wear one again soon! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Thighmax Posted January 26, 2016 Share Posted January 26, 2016 Congratulations JeffB: I recently bought two dresses. I have never tried them on. I am currently having the same problem as Guest. My wife knows about my liking of leggings, hosiery and heeled boots but she doesn't know about the dresses. She is not entirely fond of the boots but she has grown to accept them and the hosiery too. Regarding the leggings, she told me that she doesn't really like to see me in them. If I tell her about the dresses she will definitely start to think that there is something wrong with me. I am going to try the dresses and see how they fit. I don't know if I am going to like the feeling though. I will let you know if I like how they look. Link to comment Share on other sites More sharing options...
JeffB Posted January 27, 2016 Author Share Posted January 27, 2016 17 hours ago, Thighmax said: Congratulations JeffB: I recently bought two dresses. I have never tried them on. I am currently having the same problem as Guest. My wife knows about my liking of leggings, hosiery and heeled boots but she doesn't know about the dresses. She is not entirely fond of the boots but she has grown to accept them and the hosiery too. Regarding the leggings, she told me that she doesn't really like to see me in them. If I tell her about the dresses she will definitely start to think that there is something wrong with me. I am going to try the dresses and see how they fit. I don't know if I am going to like the feeling though. I will let you know if I like how they look. Regarding the situation with your wife, I can only suggest that you consider her feelings and wishes on the subject of dresses and give a lot of thought as to whether or not it's worth the trouble. Good luck to you. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Thighmax Posted January 28, 2016 Share Posted January 28, 2016 Just as an update. I have the dresses here in my office. I tried one of them on and the feelings are mixed. Even though the dress really felt comfortable I took a couple pictures and wasn't terribly satisfied with how I looked. I don't really know if it is because I am not used to wearing something like this or because it didn't really look good. I will see if the look grows on me or not. Have a good one. Link to comment Share on other sites More sharing options...
Thighbootguy Posted January 29, 2016 Share Posted January 29, 2016 The first couple of times I tried a dress I didn't like the look or feel of it. I then tries a short sweater dress and liked the look and feel a lot more. It really is about being able to see yourself attired in a dress and being pleased with what you see in the mirror. The look takes some getting used to so don't be too hasty in making up your mind. But do an honest appraisal and, if you like the look, go for it. However if you don't really like the look (and feel comfortable presenting it) put the dress back on the hanger. I dream of a world where chickens can cross roads without having their motives questioned. Link to comment Share on other sites More sharing options...
robbiehhw Posted February 1, 2016 Share Posted February 1, 2016 I agree that the first few times you wear dresses/skirts it is sort of disorientating. Never had the opportunity to try kilts in my culture as a kid, so perhaps it would have felt different. I think my first dress wearing were borrowed items in my college years. The first one i owned was later in my 20s. I'm actually wearing more and more this year. Link to comment Share on other sites More sharing options...
Thighmax Posted February 1, 2016 Share Posted February 1, 2016 I bought two dresses, one in black and white and the other one in olive and gold. I have only tried one on, the green and gold I haven't tried on yet. I took a few pictures of the black and white and it does feel comfortable and nice, I even felt really good, the problem came when I saw the pictures. If felt to me like I didn't give the dress a good form, it kind of looked like a cylinder. I kept the pictures and have been looking at them to get myself used to the look, I will try and take pictures of the other one to enhance the look further. I went on the site and looked at how the dress looked on the model and felt a little better because the dress is not too flattering. I am looking to buy another cheap dress that is more flattering so that I can have a more objective assessment to my look. I will let you know how it progresses. Link to comment Share on other sites More sharing options...
JeffB Posted February 8, 2016 Author Share Posted February 8, 2016 Thighmax: Good luck to you. I hope things work out with your purchases. Meanwhile, as I'm planning to wear dresses more because I love how they look on me, and, more importantly, how good I feel when wearing them, I'm thinking about giving a bodycon a try. Perhaps this ego, but I really think I can make a bodycon work, and I'm eager to wear one. Once I purchase one, I'll see what I can do about an outing. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
HappyinHeels Posted February 9, 2016 Share Posted February 9, 2016 Thighmax, Looking at yourself in a dress is definitely different. Especially if you have a gut, or a mustache, or beard or just aren't exactly easy on the eyes. Buy a waist reducer the same as your dress size (XL) for size 14-16 (1X) for size 18 and so forth. Consider wearing the dress with a belt. If you are going en-femme then concentrating on your overall figure is great idea. You have to figure out what you want to achieve from all this. If all you're doing is dressing at home then it is not complicated. If you want to actually go out as JeffB does then coordinating the right look is important. If you want to go out and emulate a woman then you have to spend lots of time to get that special look to make that dress really convey your personality. JeffB doesn't try to pass as a woman but he sure enjoys dressing like one. You'll find your path. HappyinHeels Link to comment Share on other sites More sharing options...
JeffB Posted February 12, 2016 Author Share Posted February 12, 2016 HappyinHeels: Well said, my friend! Everything you said makes perfect sense. Wearing dresses isn't for every guy, I consider myself extremely fortunate that I can make dresses work, and look good them, for anyone else who wants to give them a try, it's important to do everything you can to look your very best. Meanwhile, I ordered three sweater dresses over the weekend from JCPenney and are ready for me to pick up today. I can't wait to see how they look on me, then take them out for a spin. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Bubba136 Posted February 13, 2016 Share Posted February 13, 2016 Careful Jeff, it's a well known fact that women require more clothes than almost any man needs. It doesn't take long before you lady's clothing collection will be twice as large as your men's closet Being mentally comfortable in your own mind is the key to wearing heels in public. Link to comment Share on other sites More sharing options...
Thighbootguy Posted February 13, 2016 Share Posted February 13, 2016 1 hour ago, Bubba136 said: Careful Jeff, it's a well known fact that women require more clothes than almost any man needs. It doesn't take long before you lady's clothing collection will be twice as large as your men's closet I suspect it already is... I dream of a world where chickens can cross roads without having their motives questioned. Link to comment Share on other sites More sharing options...
JeffB Posted February 14, 2016 Author Share Posted February 14, 2016 14 hours ago, Thighbootguy said: I suspect it already is... TBG is right, Bubba, I currently have two to three times as much women's clothes than I do men's. HA! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
kfisher247 Posted February 14, 2016 Share Posted February 14, 2016 How can they be women's clothes if they're yours? / Link to comment Share on other sites More sharing options...
JeffB Posted February 17, 2016 Author Share Posted February 17, 2016 The dresses arrived, I tried them on and they look cool. I can't wait to take them out on future outings. While it's a tad late to make new year's resolutions, I do plan to wear dresses more as I really like how I look in them. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Thighmax Posted February 17, 2016 Share Posted February 17, 2016 That is awesome JeffB!!! I have been thinking about it and I don't really mind the look I project when in a dress, I do feel natural in a dress. My problem might be more stereotypical. Most people are used to seeing a woman in a dress and women have different figures than men. When I first saw my pictures I was expecting to see more of a woman like figure than mine. It will be a little harder to have that figure since my weight is around 190 pounds. Like Thighbootguy said, it is all a matter of getting used to the image!!! I have tried some other dresses and I do like the way I look in them. Link to comment Share on other sites More sharing options...
JeffB Posted February 17, 2016 Author Share Posted February 17, 2016 Thighmax: I'm rather proud of the image I present in a dress, otherwise, I wouldn't wear them. Like you, I feel quite natural in them and I love how I look, especially sweater dresses. As far as figures are concerned, I'll admit I do cheat a wee bit by wearing a body briefer which helps shape and smooth my physique, giving me a slimmer profile. Lastly, I regularly clock in at around 225 pounds, but, I also stand six foot two inches, so my physique is adequately proportionate to my height. And that helps make wearing dresses easier. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
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