Wednesday, January 11, 2023

I Love What You’re Wearing, “Sir”

Jasmine wrote, “A topic I would like you to explore with your readers is whether or not when not totally en femme, if they still wear feminine clothing that while not gender neutral, is something that is ambiguous enough to not potentially out themselves to others. I ask because of something that has happened twice to me that probably did out me! 

“The first time, I had on a pair of sandals that were mostly like male sandals, but were embellished on the top, which may have made them feminine enough for the comment I received. I was in Florida staying at an Airbnb and the lady whose home I was at commented in the first few minutes after my arrival about how much she loved my sandals. 

“Along the same lines, I was in male mode at a meeting, but had on female dress shoes that look like they could be for men, although they are a little bit more narrow in the design than men’s shoes and are gray in color. The comment I received may have happened because the brand was Esprit. I was told by a woman prior to the meeting that she really loved my shoes. 

“To me, both of these comments are a nice way of saying they know that I am wearing women’s footwear. Having said that, the comments are welcomed because it is no different than two women having a conversation about fashion and I love it when this happens.”

👠 👠 👠

Personally, I wear panties all the time, but there is no visible panty line, so I get away with it! But seriously, I have worn women’s sweaters, tunics, hoodies, jeans, slacks, shorts, socks and sneakers in boy mode, and nobody ever commented about it. However, a manly shirt that I wore may have confirmed my transness.

When I was still gainfully employed, our division’s HR rep seemed to be friendly with some co-workers, but she was always aloof with me. Whenever I encountered her and said, “Hello Amanda,” she rarely said, “Hello Stan.” Usually just a cold “Hello” and sometimes not even that.

Things changed dramatically after I came out to corporate HR. I assumed our corporate HR Director informed Amanda about my transness because after coming out, Amanda became downright friendly and she never missed calling me by my name when we exchange Hello’s.

So one day I wore a shirt that had a blue floral print. I bought it in the men’s department of Walmart, so I knew it was a man’s shirt. However, there is no doubting its floral design. Some guys might shun such a shirt as being too feminine or at least, too diverse.

Anyway, I ran into our local HR rep while wearing that shirt and said, “Hello Amanda.”

She replied, “Hello Stan” and then she added, “Nice shirt, by the way.”

I was very surprised by her compliment and thanked her for it.

Anyway, Jasmine and I would like to hear about your experiences wearing girl garments in boy mode. So comment below and tell all.

Source: Nana Jacqueline
Wearing Nana Jacqueline

David Tennant
David Tennant femulating on the British stage in What the Butler Saw.


  1. I have a "messenger" bag which I got for approx £20 ($24) off an auction site
    A non TG friend liked it so much she bought one for herself

  2. Haven't done it since, oh, about 6 PM, but the jeans are kinda neutral and the boots are mostly covered by the jeans and don't have a heel. The jeans are actually my favorite, a little soft and the waist a little stretchy

  3. I found it very difficult trying to maintain my two personas, and towards the end (before I "went full time") it got harder and harder. I often found that Paula would start leaking into Paul! For my last few year prior to transition I owned no male jeans, and would often wear women's boots and sweaters with my jeans.

    At least once one of my friends commented on one of my sweaters, on another occasion she commented on a quite feminine bags I was carrying some music in. She even noticed that one day I had forgotten to take off my pale pink nail polish. Somehow this same friend still expressed surprise when I did eventually come out!

    Amazingly the only time I have had any abuse was walking to church one evening wearing a masculine, but quite floral shirt when I got some homophobic abuse as I walked through the local park. If only they had realised what a big target they had missed!

  4. I always run in women’s wear. My running shirts are too short and styled to show off legs, so are definitely women’s. During colder weather I use workout leggings that are feminine. I also wear a jogging bra under my top (for support, truly) and the top is a v-neck or t-back top usually. I also wear a women’s running hat. I am very sure people notice, but the only comment I received was from one of my wife’s friends, who told me I looked “cute” because my top was color-coordinated with my hat! In other settings, I generally do not gender-bend; I simply underdress to confirm my femininity on a daily basis (I also wear exclusively women’s sleepwear, although so as not to offend my wife’s sensibilities, they are in neutral colors and are not overly feminine. Lisa P

  5. Back in the '90's I did a little fun experiment. It was to go to work wearing entirely women's clothing but as my dude self and prove that certain women's clothing worn without wig, make-up, padding, jewelry etc. are basically gender neutral.

    So off I went wearing over my panties a woman's turtleneck, women's pleated trousers in a wool blend, women's trouser socks, women's flats of a quasi men's wear style, and all topped by a tweed blazer in a relaxed cut. I totally looked like a dude but wearing as my wife would say, "whippy clothes for a man", or the "Designing Women" look, wearing menswear inspired duds.

    At work I took pictures of me in the ensemble and at home added a bra and breast forms, hip padding, make-up, earrings, necklace, bracelet and wig for more pictures.

    What a contrast those items made to the clothing, which now screamed exclusively female. Took more pictures and wrote a story for our local crossdressers support group gazette.

    Angel Amore

    Angel Amore

    1. And where can we read this article and view these photos???

    2. I don't believe the STLGF support group has their old gazettes digitized yet. If you go to my Flickr site and are a member, the first picture of me in that turtleneck, picture circa 1995 or so is me presenting female. If you scroll down the page further you will find a picture of me seated wearing a black pencil skirt and the blazer I wore to work as a dude. I can't find the actual pictures but wish I could.
      To find my Flickr site, search under "people" for "angel2bb2002". Since Covid there is a lot of old stuff on my site.

  6. I do all of the cooking and wear aprons - my favorite are much more feminine than the others but most are more feminine at least in color etc. We have a set of hooks in the kitchen and when we have guests I wear aprons that are 'less' feminine. I/my wife used to put them away when guests came to dinner - we usually gather in the huge kitchen. We don't put them away any longer. So those that know I do all of the cooking might be speculating. We do believe that some know that I am special.

    I wear panties at all times except when going to the doctor. So this is really how I finally understood the real me. I used to take my underwear off in bed every night when sleeping. This started in my mid to late teens. My wife would be amused because I was asleep but would kick them off. I started wearing panties more for play but soon discovered that I did not take them off while sleeping. It was kind of weird to process all of that.

    1. I too do a lot of the cooking and baking. I've purchased several retro-1950's bib aprons from sellers on ebay who use terrific fabric/patterns. At retail stores the only aprons that are available are cartoonish patterns or aprons covering waist down. Since I only wear dresses when en femme I want to keep waist up clean also.

      It took my awhile to wear panties all the time. My preference is a Vanity Fair nylon brief in either black, white or beige/fawn. The colors are reserved for when I wear a dress.

  7. I do not present feminine in public (at least yet). But I do like to wear women's clothes as much as possible. So yes, I do love "stealth crossdressing" in public. I underdress everyday I go out but obviously no one sees that. But I do wear women's GV jeans which I love. If I go out to dinner with my wife I'll wear a button down blouse and ladies pant suit (minus jacket). Other than the blouse buttons to the left and pants zipper to the left they aren't that noticeable. I have no idea if ladies notice. Some probably do. My guess is most men do not. lol. But I feel happy.

  8. I am fortunate a mens8 or womens 10 shoe. My wife order us matching gray half boots(womens). Heel is slightly higher than a mens. I wear my wife’s flip flogs all summer. Beige pair and black thong like sandal. Along with four toe rings. My neighbors all see. Ask me where did I get the nice sandals. They were my wife’s! My life my feet. I care what people say. My wife’s friend gave me a pair of slippers and sandals she is a 10 size wear them too.

  9. When the weather is warm I like to wear sleeveless dresses out in public. And I alternate between wearing a dress along and heels to church and wearing a man's coat and tie outfit. I also wear nail polish. I have hair beyond shoulder length and my natural bra cup size is DD.
    I have NEVER been hassled about my attire.
    The one thing that is not feminine is my voice, as the speaking and singing voice is bass bordering on basso profundo.
    So I present like a woman.but have a very masculine voice.

  10. I am also lucky that I wear women's size 10 (sometimes 11) shoes. I have women's shape feet and men's shoes never really fit. Women's feet are more pear shape while men's are rectangular. During my life men's shoes caused hundreds of ankle twist and several ankle reconstruction. All that changed (stopped) when I started to wear women's shoes over a decade ago. Most of the time I am in 4+ inch heels - today knee high 9 West leather boots. But I also wear sandals, wedges, stilettoes, etc.
    I had a major injury and my urologist "suggested" I start wearing panties, so I have been wearing mostly VS thongs for almost 20 years.
    In the last 10 years my closet has transition to items from the women's side. At least 90% of the clothes I wash are women's. I have only worn male pants a handful of times in recent memory, luv my stretchy skinny jeans, and my leggings and shorts.
    And I present male even with gel fingernails and polished toes.

    PS: I got a sherpa and I have had equal number of males and females ask me where I got it because they wanted one themselves.
    PSS: Wear what you love - love what you wear. Be yourself.

  11. This is Meg's comments on the matter. She emailed them to me because she thought they were too long, but I think they are just right, so here they are:

    I used to be a "all or nothing" dresser, at least where it matters. I gradually started tossing men's clothes for women's, but women's clothing in men's styles as much as possible in every day life.

    My shirts were button-down in solids or stripes in neutral colours. They had no darts, and a pocket, or a faux pocket.
    My undershirts were tank-top camisoles in colours to match my shirt.
    My pants had four pockets, a fly, and could support a belt. The pockets might be tiny or fake but the front slanted.
    My socks were often tights. I wore most patterns or colours, often trying to co-ordinate with my shirt, but I eschewed tights that showed skin (ie, no fishnets for me). I wore women's socks in almost any pattern ~ if anyone commented, my go-to was "I don't wear ties so I wanted a little colour and style somewhere.
    I mostly wore panties, with a few "tighty whities" for doctor visits.
    My shoes were mostly running shoes, women's styles in subdued colours.
    My arms/legs/chest were shaved. My brows were trimmed.
    My eyeglasses are from the women's side of the optician but not too femme.
    I usually wore two rings (wedding and some other band), a necklace that's sorta guy, and a charm bracelet.

    Gradually, I started wearing more femme clothing, but things that were still masculine-at-first-glance. For the past few years, through retirement:

    I might wear polka dot or flower shirts. Pockets might be absent, or I might have two. I don't care about darts.
    My camis became more... interesting. Spaghetti or adjustable straps that might be noticeable if I was hunched over my desk.
    I have purple pants, pants that don't take belts (although I usually wear them with untucked shirts), pockets might be absent or straight across in the front. The fly might be small to the point that stalls are difficult.
    In addition to tights, I mostly wore knit socks my wife made or knee-highs in mostly black or taupe.
    I only have panties now. A year ago, I made a visit to the doctor, where I had to strip down completely. She noticed my panties (on the top of my pile of clothes) and painted toenails and initiated a conversation about possible "next steps."
    I've worn flat Mary Janes and loafers with (slight but noticeable) wedge heels.
    When I bought my most recent glasses, the optician's assistance said to me, "are you sure? They're not very masculine frames." I said to her, "did you notice? I don't have a very masculine frame."
    I have pierced ears now and wear hoops or a variety of dangly earrings. My right-hand ring might have CZ or some other cheap gems on it, and my necklaces are more daring (although I've never tried pearls and some beads seem too girly for guys). I have a variety of bracelets.
    I generally wear a lipstick that's not too far from my lip colour. I add gloss which is probably noticeable. I will say, when I went to work, my lipstick was usually transferred to my coffee cup before most other people came in.
    I've never worried about VPL and I wore bras padded to AA or A and just "fluffed up" my shirt and it's not really noticeable, although people might notice the straps from the back.

    In shorts weather, I only own women's shorts and sandals. My toenails are usually painted and I never had a negative comment. Sometimes, I wear nail stickers in whatever pattern my wife happened to buy (or whatever pattern I bought her) and I've gotten positive comments on that, usually from women a third my age:
    "I love your nails! Where did you get them done?"
    "My wife is a wizard."
    "Are they stickers?"
    "Oh. I was going to ask if she does nails for other people."

    I've pushed the envelope in other ways, but you specifically asked about androgynous habits so I'll stop here.

  12. Thanks for covering this topic, Stana, and thank you to all the ladies who responded here. I enjoyed reading all of your responses. Beyond shoes, I also enjoy finding feminine clothes that I can wear in public when not totally en femme. An interesting side note is that a person I knew who played a sport that I play and who I thought was a civilian until this one day when I saw him in the grocery store wearing a gender neutral top that I also own. That was quite the eye-opener! Needless to say, I was so happy that I wasn't wearing the same top that day. I really hate when that happens!

    1. It's even funnier when your ex stops by and she has the exact same sandals as you have on. Then she askes to borrow your nail polish ....

    2. Melissa RobertsJanuary 13, 2023

      Like Stana, I wear panties all of the time. In fact, I don’t own any male underwear anymore. Up until a few years ago, I had a single pair of men’s briefs for the sole purpose of going to doctor visits. Then I realized how stupid that was being that my primary doc and my dermatologist (both female) know that I am a crossdresser. They know because I told them, stemming from conversations about me maintaining a completely hairless body. So then I began just wearing some kind of solid color hipster panty, usually black or gray that could easily be compared to a men’s bikini brief. That all changed this past November when I had my annual dermatology skin check up. Instead of the usual plain panties, I thought what the hell and wore something much more feminine, my Warner’s No Pinching No Problems Hi-Cut Brief in the color of Lavender Aura Floral. (check them out online, they are pretty) For this check up you strip down to your underwear and put on the paper gown with the back open. Sitting there waiting for the doctor, I was anxious about what her reaction might be, if any at all. I soon got my answer. The doc came in with her assistant and started the exam. She asked me to stand up and came behind me to check out my back. “Ohhh, someone is feeling pretty today.” she said. There’s more to tell but I’ve already been long winded. Just know that I was on cloud nine!