Friday, April 26, 2024

Bifurcated Crossdressing

After reading Hannah’s post and Rhonda’s post about dressing to blend or not, I thought about my progress as a crossdresser. 

As a novice, I wore dresses exclusively. I was of the opinion that if I wanted to crossdress wearing pants, I might as well forgo the wig, makeup, heels, handbag, etc. and go out in boy mode. 

In that distant past, my “outings” were to support group meetings or a rare support group-sponsored outings to a restaurant, beauty salon, whatever. I wore dresses during those outings and I blended in because all the other crossdressers were wearing dresses, too. (Ironically, the only attendees wearing pants were the wives and girlfriends who accompanied their “girls.”)

I started reconsidering my dress-only policy when I decided it was time to mix it up with the civilians (after being closeted* for too many years). So I bought a pair of gray leggings to wear for my debut in the real world. I paired the leggings with a black tunic sweater and black boots. (Click here to read about my first day out among the civilians.)

Since that first outing, what I wear out among the civilians depends on where I am going. I still prefer to dress to the nines, but in many situations, dressing to the nines is over the top and I have to pull back a little and dress to the eights or even the sevens.

Meanwhile, I have expanded my wardrobe to include many bifurcated garments. Since they are female bifurcated garments, there is no mistaking them for male bifurcated garments. The lack of pockets, zippers on the side, their tightness, fabric, length, color, etc. are some of the giveaways that the trousers you are wearing are milady’s and not my gents.

So, yes, it is still crossdressing if we wear pants.

* In my opinion, attending support group meetings/outings, trans conventions, etc. is as closeted as dressing at home… they are just bigger closets.

Source: Boston Proper
Wearing Boston Proper

Yes, it’s still crossdressing!


  1. What a gorgeous colour in that Boston Proper outfit!

  2. I love leggings and I love women's slacks. However if you have an exaggerated upside down triangle male body, like I do, you are stuck wearing padding on the bottom. This padding is not only uncomfortable for the most part, it can look ridiculously unnatural if you are not extra diligent. Most dresses and skirts are much more forgiving, with or without padding.
    And so it goes. (I can't help that Stana, it's too good of phrase)
    Angel Amore

  3. I blend in fine. I buy sweat pants, ratty sneakers, flip flops, university t shirts and sweat tops from thrift stores. On date night it's Lululemon yoga wear, new Addidas and a nose ring with earings. I only dress like Stana working from home. When shopping at the Piggly Wiggly I choose dirty clothes or the ones with holes and tears in them and I blend in fine. I do get dressed to the minds when going to the movie theatre as that is a big deal these days.

  4. I have zero interest in blending in with the 95% of women who are out in pants in any given day. I wear skirts and dresses to feel feminine and special and, for me, nothing compares. I naturally move and behave like a lady in a skirt. I was out just the other day in a lovely coordinated outfit featuring a red and white floral fit and flare dress, and I got compliments from a store clerk. “You look so nice! Are you on your way to a special event today?” I thanked her and replied “No, I just wanted to feel pretty and special on this beautiful day. “

    1. I happen to agree that when I am dressed en femme (which is the great majority of time) I am going to wear a dress. I'm tired of seeing women wearing trousers the great majority of the time instead of skirts or dresses.
      And that includes when I go shopping, to church, and to doctor appointments.
      And I don't need wigs as my hair is several centimeters below my shoulder. I don't mess around with stick on fingernails; I paint my fingernails a different color each Saturday night. Speaking of doctor appointments...

      I had a very interesting experience about two months ago going to a doctor appointment. I wore a long sleeve maxidress and makeup. The nurse, who remembered me, asked me how my job at Victoria Secrets was going. Of course I didn't know what she was talking about.
      It turns out there's another patient, born as male, like me, is on estrogen and, unlike me, is transitioning to be a woman. And she had breast augmentation, which I definitely don't need (my bra cup size is DD). Also she likes to wear dresses as I do. I asked what her voice is like, and the nurse said her voice is not as deep as mine, probably a baritone. (I'm a bass).
      And the the piece de resistance: She's a bra fitter at Victoria Secrets.
      And of course I joked with the phlebotomist (who is very good) about using a razor blade and aiming for the bucket.


  5. Well done! Unfortunately, one factor that attracts attention quickly and perhaps gets one made is to wear a skirt or dress. Pants it must be....

  6. When I was growing up in the 1950's women, no matter the occasion, wore dresses. There was one woman, a divorcee, who wore pants and she was shunned for both reasons; pants wearer and divorced. I know there a many "girls" who are tall and bulky. I check in at six foot even and 200 +/- lbs. Figure wise it's 42-40-40. I'm self conscious of the bulk. So, along with my exposure to dresses as an observant kid and bodily form I wear dresses that do not have a defined waistline; empire waists, sheaths and wraps. If I was more adventurous I would not join the masses of women in the stores attired in pants or leggings. Don't get me wrong. I see some very attractive females out there in patterned jeans that are drop-dead gorgeous. I posted several times on another site that once I was driving home and waiting for a light to change. This gorgeous young woman got out of the cab of a cement mixer attired in steel-toed work boots, jeans, flannel shirt, safety vest and hard hat. She has long reddish blond hair and a great big smile. If I could look like that -maybe- but my thoughts were, that woman knows where the money is. Me? No matter, if pants or dress, the world knows I am a guy. So I want to look as feminine as possible.

  7. It’s still femulating. I prefer dresses and skirts.

  8. Late to the show, but here goes.
    I wear pants (including shorts) most of the time. Only on very rare occassion they are from the men's side. I like the stretch in womens pants, and how some styles will help to frame your back side without padding. Skinny jeans fit nicely into your knee highs. With the style changing to wider jeans, I'll have to adapt.
    Leggings and slacks are super comfy. Give them a try.

  9. Pants can definitely be part of a fabulous feminine outfit, especially if worn with heels and a pretty top!

    As a stay at home CD, I always dress in pantyhose and too-tall heels because that is what makes me happy! But I can definitely understand the conflict between wanting to wear whatever you want vs. wearing what it takes to fit in.