Awkward feeling when talking to females about feminine fashion

[MackyHeels]

Talking to female acquaintance about my feminine fashion leggings i was wearing on purpose to be seen by her today. Days ago she encourages me to purchase her same type of leggings  she was wearing, telling me it would look great on me. I told her i have some older ones yet she didn't believe me. So i decided to wear them today in case i ran into the married female acquaintance. She gave me thumbs up with a smile  from a distance, so i had to walk towards her to chat showing off my leggings comparing the differences to her new ones. She was happy and wished to be wearing same leggings. Her laughing out loud saying she and me would be wearing exact same ones only last minute decided to wear her other ones leaving the house. Her replies and comments to me was  i told you so, the colour stands out really well, looks great. She began to talk about other leggings she wanted to purchase but found them sheer showing her underwear beneath deciding not to buy them, as i stood silent while she closely observing my reaction. At the time i spoke very little almost stoic, finding it all to awkward to discuss wearing female fashions in public with her. Don't know if i'm in shock or waiting for the other shoe to drop with this wonderful married female acquaintance.  

Just want to know if anyone discussed with  strangers, a woman in particular about their style and certain female clothes or heels that you as a male can wear?

 Find the discussion to surreal to be talking to a woman about female styles that look good on me to be wearing. Often then not majority of women have a belief male should never think or speak of or even wear any female styles be it heels or clothes made for woman. Just find the discussion very new to be able to talk freely about style or fashion, like we are two girlfriends, sipping on hot coco in our PJ's sitting by a with warm fireplace on Christmas day, with another woman and her being so comfortable or encouraging me to wear it. 

Never have i dreamed a woman can feel comfortable seeing a male like me wear her style clothes yet encourages me further to purchase such fashions while in society norms being taboo for me to wear. 

Feelings of doubt creep in that this acquaintance will shift her beliefs upon me laughing what i wear as entertainment not believing what she was saying to me as truth. Lying to me as some sick joke playing a game on how far i would go to dress up as a woman.  So i lack any faith in the woman i seldom see encouraging me to wear her type of clothes. Often fear sets in closing myself off to her any woman believing there cool with me wearing female styles. Feeling of being made as experiment like some little boy that teen girls will make him into a little girl finding it as a fun game rather than real truth finding it disturbing for male to able to wear other genders style.

 

Edited September 27, 2018 by MackyHeels

[HappyinHeels]

Mackyheels,

If she initiated the conversation then it is okay. I would be mindful it is at work and would never stray far from that. You want to to sociable but professional.

I have talked to many women about female fashion without any problem. Part of it is age I think and part of it is how I am dressed myself. If I walk into a store and am greeted by a saleswoman and am wearing 5.5" wedge sandals with painted toes, a woman's style dress watch, and carrying a handbag then I will probably get a nice compliment and a conversation about any of the the articles I'm wearing may soon follow. Women are naturally curious especially as it relates to fashion. Don't be too shy but know your audience. HappyinHeels

[MackyHeels]

Happyinheels it’s not at work but at the gym. She seen me for years  but seldom did I talk or say hello. Yet when she was single felt she found me somewhat attractive but I never intitated conversation unless others joined in forcing me in some dialogue. 

Find her encouraging attitude towards my style odd always felt she was like others scoffing at my feminine tight clothes in the gym. For whatever reason she voices her opinion about me  maybe feeling comfortable to say what’s on her mind without fear.  Noticing another married  woman at the gym being friendly admiring my body in long conversations with me. 

[HappyinHeels]

Okay, the gym is a bit different. This lady has taken the time to give you positive feedback. Perhaps it will encourage others to do the same?? The world needs more positive souls and fewer negative assholes.  HinH

[CrushedVamp]

I dress typical to my male gender but often find myself in discussion with women about female clothing. I have had a few women ask why I am so open about it and just told them the truth, I am a writer and often describe women's clothing in my novels. I just know clothing, men and women, and since I have done some historical novels, I even know some about the history of clothing. I mean you cannot say "underwear" in a novel based in 1771 Virginia; your readership will call you out for poor research.

Just yesterday my step-daughter needed some tights (not pantyhose) for school and her mother and her were trying to figure out where to buy them. I told them Wall Fart carries them. Neither knew that, but just from being with her mother in buying hers, I saw across the aisle they have a leggings/tights section.

I have even had to buy female typical clothing alone before. In both cases it was pantyhose. Once because my wife had hers ladder so bad she refused to go into the store to buy them and sent me in to get replacements, and another time I needed some high denier stockings as a prefilter for my shop vac. Each time I just openly stated what I was doing. "These are NOT for me I assure you", I said in such a grandiose way that all suspicion was thwarted, "my wife refuses to come in because hers laddered", and saying I needed "a prefilter for my shop vac".

I say this because if people are buying this stuff for themselves to wear and are nervous about it, just do what I did and use my real reasons for an excuse for you. It should not matter why you  are buying it, but if it bothers you, a little white lie never hurt. Tell them you need a prefilter for a shop vac! 🙂

[Shyheels]

I have a couple of female friends on Instagram with whom I chat about fashion, one of who me was instrumental in convincing me to try a skirt - the midi skirt I bought a couple of weeks ago.

The people at the shop where I bought it knew the skirt was for me, or at least they guessed it was. I didn’t say anything either way, just made it a straightforward ordinary transaction. 

[bluejay]

On 1/26/2025 at 4:17 AM, CrushedVamp said:

I dress typical to my male gender but often find myself in discussion with women about female clothing. I have had a few women ask why I am so open about it and just told them the truth, I am a writer and often describe women's clothing in my novels. I just know clothing, men and women, and since I have done some historical novels, I even know some about the history of clothing. I mean you cannot say "underwear" in a novel based in 1771 Virginia; your readership will call you out for poor research.

Just yesterday my step-daughter needed some tights (not pantyhose) for school and her mother and her were trying to figure out where to buy them. I told them Wall Fart carries them. Neither knew that, but just from being with her mother in buying hers, I saw across the aisle they have a leggings/tights section.

I have even had to buy female typical clothing alone before. In both cases it was pantyhose. Once because my wife had hers ladder so bad she refused to go into the store to buy them and sent me in to get replacements, and another time I needed some high denier stockings as a prefilter for my shop vac. Each time I just openly stated what I was doing. "These are NOT for me I assure you", I said in such a grandiose way that all suspicion was thwarted, "my wife refuses to come in because hers laddered", and saying I needed "a prefilter for my shop vac".

I say this because if people are buying this stuff for themselves to wear and are nervous about it, just do what I did and use my real reasons for an excuse for you. It should not matter why you  are buying it, but if it bothers you, a little white lie never hurt. Tell them you need a prefilter for a shop vac! 🙂

I never have a problem buying anything from the women's department at all. Sometimes I buy for my wife but mostly it's for me, which includes pantyhose, tights and leggings among the many  things, that I buy for myself.

Happy Heeling,

bluejay