So very thoroughly confused!

[pebblesf]

Good for you buddy!  I agree, there is nothing that feels quite so liberating and amazing as being out and about dressed the way we want...

[RonC]

Just curious, are you wearing any type of legwear with the skirts, or bare legs.  If bare, are your legs shaved or perhaps you have minimal leg hair?  Personally, I'd have to wear some type of hosiery to feel comfortable at all with my legs showing in a skirt, or have hair free legs at least.

[mlroseplant]

14 hours ago, RonC said:

Just curious, are you wearing any type of legwear with the skirts, or bare legs.  If bare, are your legs shaved or perhaps you have minimal leg hair?  Personally, I'd have to wear some type of hosiery to feel comfortable at all with my legs showing in a skirt, or have hair free legs at least.

That's kind of a touchy subject with some people. The OP said somewhere back a couple of weeks ago that he didn't want to shave his legs. For me personally, that's simply not an option. Well, anything's an option I suppose, but it's certainly not an aesthetically pleasing option. It's all a matter of opinion, of course, but I personally would never show my legs in any sort of feminine-leaning garment without shaving them. Even before I started shaving my legs, I shaved the tops of my feet and a bit around my ankles so that I could wear sandals without bits of fur sticking out around the straps. I guess I feel that having hairy legs when wearing shorts (or for other people, a skirt) doesn't present the sleek, polished appearance that I am going for. Others will have a different opinion, I am sure.

[JeffB]

To add my two cents worth (inflation factored in), I’d say that it’s understandable that you expressed confusion over how quickly you went from just a guy who wore heels to a guy in a skirt and heels. For those of us here, myself included, that evolution occurred over the course of several moths, perhaps even years, it all depends on the individual and their own mindset about how much to wear in terms of women’s clothing.
 

I’ve been wearing skirts with heels full time on my outings since 2014 and I’ve never looked back because I love how I look in womenswear, I’ve also added dresses to the equation as I look smashing in them, and that’s the important thing, that you feel supremely confident in your appearance and that it’s no big deal for a guy to wear skirts and heels in public....because it’s not. As long as you feel confident about yourself, then the sky is the limit. Since you’re just beginning your journey as a fashion freestyler, I would suggest that you take things slow, there’s no need to rush into things when it comes to outings and such. Also, it wouldn’t be a bad idea to study up on fashion, to learn what women wear, why they wear it, how they wear it and take it from there. 

[Cali]

I would also suggest that you slow down, enjoy the journey. You need time to digest things. 

I have a couple of skirts, but I not into outings in skirts, it just something I'm not trying to add to my life.  I don't do "outings"  in heels, I live my life in heels.  Instead of skirts I wear short shorts in the summer.  I've damaged my legs and ankles to the extent that I need to tape them up to do certain activities. Hair and tape don't mix so for the past five years I have been waxing my legs, I hate stubble!!!! I have them waxed 4-5 times a year (I purchased a multi-wax plan). The first  couple times was slightly painful, but now it's nothing. I also have very little hair and what's left is light colored now, but enough that I still need to get it removed.

[SkirtDude]

Glad your trip to the shops went well, @hiddenheels. It can be very nerve wracking the first time out. Observing how others dress helped me. There's this guy on Pinterest who has it down to a fine art, with a kind of corporate chic. So even in the workplace, fashion freestyling can work. 

Take your time to find a skirted style that works, this can take weeks or months, I understand the trepidation to share a picture, but one (with head cut off) is fine if you want critique or pointers 

 

Edited March 7, 2020 by SkirtDude

[hiddenheels]

Thanks for all the votes of confidence, and support! I will definitely take it slow as the chances for me to explore won't be there for the next few weeks or more. Since my venture to the store, I feel much more relaxed and less anxious, about this, and in general. That was fun! Seriously.

I'm hoping to have some time and just explore the styles at home, see what works well, and what doesn't. I've experimented around a bit, and certain outfits were "OMG, this looks amazing!" to combinations that were just OK. Need to take some photos so I can remember what looks good.

Regarding shaving, I can't. It's not something I would like to do, nor can I. My wife would definitely ask questions, and it would be even further from the masculine image she's trying to preserve. I did not like the look of my somewhat-hairy legs with a skirt, and started looking at tips on YouTube. Found one video talking about using skin-colour tights under pantyhose to hide hair, which I was able to try out, and it works amazingly well. Put on the opaque tights, and then either brown or black pantyhose, and it looks exactly like a nice clean shaved leg. It was a good tip, works very well for me! So that's what I did a few days ago.

The last few days I have been surprisingly calm. The anxiety has left me. I don't have any specific plans for going out in the near future, so I'm just enjoying being content...

[HappyinHeels]

hiddenheels,

I wanted to offer some alternative reasons why men may shave their legs and/or arms which are have little to do with wearing hosiery or skirts or dresses and are not controversial. These include cyclists, body builders, football players, baseball players, and swimmers. I have always found it interesting, and odd, that women do whatever the hell they want to their bodies and everyone else just has to roll with it. You could shave for reasons only you can articulate but that does not mean you will change how you love and treat your wife. Once she figures that a small change in your body's appearance is no meaningful threat to her then I believe she will roll with it as well. The smart money says she will not take off if you shave it off. Fingers crossed confidently. HinH

[Cali]

I wax my legs so that I can tape them, its been years since I had hair on them.

[SF]

I don't shave my legs generally, but I do take care of the hair on my feet and toes.  I wear sandals almost exclusively and never liked the look of nice sandals with hairy feet - and I'm not that much of a hairy guy.  I tried shaving and that worked, but the ugly annoying "stubble" was there a few days later.  Years ago I tried using fine tweezers to pluck the hair out.  It took some time but got rid of the hair and my feet were hairless.  The hairs did grow back eventually but over a longer time period.  I continued to "pluck" and guess what?  I now have hair free feet and toes.  The constant plucking caused, for whatever reason, the hair to mostly stop growing.  About 90+ percent or more of the hair is not there anymore.  Gone.  

It took some time and tenacity to regularly pluck the hairs, but it seemed to work and eliminating the hair was a pleasant unintended consequence.  Might not be for everyone but maybe something to consider.  After all, if you are going to wear sandals (guys or gals) you feet should look nice.  And consider a pedicure as well!!  

Have fun all......   sf

[ohnoberty]

Well as HappyinHeels has posted, swimmers and cyclists are notorious for shaving pretty much everything off them. It could be an excuse, buy a bike and some cycling shorts, and shave away care free. Speaking of arms, I've always had the finest of hairs on my arms to the point that they basically look bare and shaved. It's odd because you always seem to want the opposite, or at least I did when I was younger.

[mlroseplant]

19 hours ago, ohnoberty said:

Well as HappyinHeels has posted, swimmers and cyclists are notorious for shaving pretty much everything off them. It could be an excuse, buy a bike and some cycling shorts, and shave away care free. Speaking of arms, I've always had the finest of hairs on my arms to the point that they basically look bare and shaved. It's odd because you always seem to want the opposite, or at least I did when I was younger.

I can certainly relate to that! I was a somewhat late bloomer, and always wished for more hair. Tried to grow a beard at 18, and it was pretty pathetic. Now I am one of those guys who can grow a beard in a day and I don't want it! We won't even talk about hair migrating down from your head to your nose and ears.

20 hours ago, SF said:

I don't shave my legs generally, but I do take care of the hair on my feet and toes.  I wear sandals almost exclusively and never liked the look of nice sandals with hairy feet - and I'm not that much of a hairy guy.  I tried shaving and that worked, but the ugly annoying "stubble" was there a few days later.  Years ago I tried using fine tweezers to pluck the hair out.  It took some time but got rid of the hair and my feet were hairless.  The hairs did grow back eventually but over a longer time period.  I continued to "pluck" and guess what?  I now have hair free feet and toes.  The constant plucking caused, for whatever reason, the hair to mostly stop growing.  About 90+ percent or more of the hair is not there anymore.  Gone.  

It took some time and tenacity to regularly pluck the hairs, but it seemed to work and eliminating the hair was a pleasant unintended consequence.  Might not be for everyone but maybe something to consider.  After all, if you are going to wear sandals (guys or gals) you feet should look nice.  And consider a pedicure as well!!  

Have fun all......   sf

I definitely de-fuzzed my feet long before it ever occurred to me to shave my legs. Now that I think about it, I have done this occasionally since reaching puberty. I've paid attention to my feet for that long. Thanks a lot Mom, for giving me these chubby toes! I work with what I got. At least my nail beds are reasonably long. It could be much worse.

Edited March 18, 2020 by mlroseplant
Spelling error

[hiddenheels]

Been a while... With the lockdown opportunities are impossible to come by, so movement on this front has to be put on hold... At least I can spend some time reading about it, and trying to figure out in my head what it is I really want to do. 

 

I did have one outing a week or two back which it looks like I didn't post about. Was able to go out, it was dark already. Recently I bought a red plaid mini-skirt (my all-time favorite look). Black pantyhose, 4" stiletto heel boots, white T-shirt and black jacket. The look was simply amazing. The skirt very comfortable. It took a bit of effort to get out of the car, but I ended up walking around several blocks, including by a large road, for 30 minutes. It was dark, and I was stressed out of my mind for the first 5 minutes or so. Then I started relaxing and enjoying it. It was an amazing experience...

 

The skirt looks something like this:

[RonC]

That sounds like fun.  Wish I could do that right now!

[mlroseplant]

18 hours ago, hiddenheels said:

The skirt looks something like this:

Man, I'd have to do a LOT of shaving to wear that skirt.

[Heelster]

On 3/31/2020 at 8:11 AM, mlroseplant said:

Man, I'd have to do a LOT of shaving to wear that skirt.

yep = = = and a shirt to cover everything else !!

 

[Kasiioro]

On 3/30/2020 at 7:17 PM, hiddenheels said:

Been a while...

How are your skirts doing? Are you making it further? Have you spoken to your wife yet? It's been a lot of years and I'm curious. You could continue with the topic.

[Shyheels]

Things have grown rather quiet here in recent months. You could be waiting quite a while for a response from the original poster…

[HappyinHeels]

Hiddenheels,

Had to review this thread and saw my detailed reply as it related to shaving. Now you’re curious why the urge to try skirts has taken over. You think that it is “out of your character.” I’m here to tell you it is in your character but you didn’t know it until now. Just about any of the members could describe their journey and a common denominator is they all, we all, eased into it and figured out what we were comfortable with. Many enjoy their heels or other fashion choices completely in private yet others will try their outfits in subdued settings or at night yet others like me have worn heels with other items in various settings and have met several members here. I have also attended some functions such as weddings and a few parties completely en femme. Each has to find their place and have the confidence to make it happen. There’s never been a better time to be alive if you want to express your character via your own fashion. We all like heels and that’s why we’re here but it’s only natural to see what else you want to wear those heels with. We’re here to cheer you on. HappyinHeels 

[Shyheels]

Fashion is a language and, as a writer, I can totally appreciate the desire to experiment with different modes of expression and styles. Having opened myself to the idea of wearing tall boots and heels, I’ve settled quite comfortably into the boots and jeans style and am happy there. I found my niche. Others may want to experiment more. The important thing is to be yourself and embrace that self. 

[bluejay]

Like you HappyinHeels, I like wearing skirts with my heels, especially skorts. Even my wife is OK with me wearing a skort. I love the experience with wearing women's clothing even though I'm a straight guy. I get compliments on my choice of apparel from both women and men. So guys if you want to try something from the other side of the fashion aisle, do it.

Happy Heeling.

bluejay

[hiddenheels]

Hey! Been a few years since I started this thread. Much more comfortable with skirts now, don't really give it a second thought. I told my wife, she's not supportive, so like with heels, it's something I need to work through myself. Skirts and heels, usually no problems, but still wished it was more mainstream. Or at least you could see guys wearing them once in a blue moon, but never.

Agree with HappyinHeels, it's likely that this was always in me, but just came to realize it now. The good thing is that the anxiety has gone away. I'm not saying that there are no butterflies at all, or that I don't sometimes get into my head before getting out of the car, but the progress over the past 2 years has been huge. I've often shopped for heels or skirts while wearing heels or skirts. I tend not to wear both at the same time, maybe one day.

Tend to frequent malls or restaurants and just enjoy myself. It's a LOT of fun.