I went on vacation this weekend and while moving through the various airport checkpoints, something stood out to me — most of the women were dressed extremely casually. One would probably even say that they were bummy: sweatpants, baggy t-shirts, flip-flops, basketball shorts, etc. I can totally understand, the airport can be a stressful place and being in comfortable clothing probably makes things a little easier.
Of course, there are plenty of other places where you can observe this type of fashion and my observation is nothing new. What I wondered though is whether or not transgendered people and crossdressers feel extra pressure to always look and dress their best.
When I run errands, I usually take a similar approach to my style of dress. I’ll typically wear shorts and a t-shirt, because I don’t care to take the time to dress up for something as mundane as doing the groceries or filling up on gas. However, it’s common knowledge that most cross-dressers dress up in their finest outfits and accessories when they go on an outing, even if it’s just to the post office.
My first drive en femme was quite similar, I was in a nice dress with cute jewelry and my makeup on-point. There was absolutely no need for me to be looking so nice, as it was nighttime and I had no particular destination, it was just a casual trip. Putting that in perspective makes it seem just a tad absurd. Can you imagine dressing up in your best formal wear (tuxedo or evening gown) just to walk to your mail-box and bring in the newspaper?
If you are a transperson or a crossdresser, do you feel the need to always look your absolute best? If you once felt that way, has the pressure faded away over time or do you anticipate it doing so?
One of my personal challenges is to loosen the restrictions on what I should wear when cross-dressing and be able to be casual or trendy. After all, most women do the same 
.
JessicaWhoHD
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{ 12 comments… read them below or add one }
A good question Jessica. I think that if I were 24/7 I would find ways to slouch through the odd day like the rest of the world does. However, being an occasional dresser, I always find it worth the effort to very carefully unearth the inner woman and present in the very best light.
I do rather wish that more women took more care dressing, everywhere.
Thanks – Petra
I dress casually most of the time because most women do and because I often find women’s clothing more comfortable that men’s . I see no reason to overdress.
Jes, In my opinion the normal dress in the US has gotten way too casual on the female population in general. I try to dress fashionable always and reserve finery for a true night out.
So, I never go out with just a t-shirt and flip flops but I have learned to still look nice and put together whenever I go out. Lately I have gotten many comments on my recent pictures taken in more of a casual setting and the concensus is “I look like the girl next door”. I don’t quite agree but I am probably at my peak of looking natural. I am still a little concerned of “standing out” in contrast to the t-shirted ladies out there. If you are creative, you can fine me on facebook and tell me what you think.
The world would be a lot better dressed if watching What not to Wear was required viewing at least a few times.
Ellen
I would say that I try to look my best because it is an opportunity to wear the things I CAN’T wear otherwise. I wrote an essay along these lines not too long ago about how GG’s are allowed to wear heels and hose etc, but choose not to – so why can’t those of us who WANT to do it be allowed to do so?
To answer your question – I still “dress up” (nice dress or skirt/blouse, heels, etc) just to do housework on most occasions just because I have no where else to go when “dressed up”. If I could spend an occasional night out with the girls, maybe then I’d do my laundry dressed in sweats and a T shirt.
“Forever in Pantyhose”
Julie Michelle
Interesting question you bring up, Jessica.
In my opinion, femininity is taken for granted by most genetic women. After all, it’s just the way things are for them.
But for many of us, it’s something we embrace and never take for granted. Looking as feminine and attractive as possible is something we desire and will almost always sacrifice comfort.
Personally, in either mode I’m never “bummy”. I always try to present in the best possible light .. male or female.
But there’s a big different of opinions between most TS’s and CD/TV’s. TS’s want to look like average women no matter how she appears. And therein lies a problem. Almost all of us begin to look quite masculine without much makeup, proper undergarments, heels, hosiery, etc. Nice gig if you can really pull it off, but most of us just can’t even, though we’re able to rationalize what we see in the mirror.
For many, the desire to fit in is strong even if that means becoming almost invisible in a crowd of “bummy” women.
It’s certainly up to everyone to do as they choose, of course, but I’ll continue to try my best to look and behave as feminine as possible even though many would consider those like me to be a caricature of a “real” woman.
And wearing heels to the gas station gives me a better angle on the credit card swipe thingy at the gas pump!
Just my opinions of course .. your mileage may vary. *giggling*
If I’m cross-dressing, I like to make an effort but that doesn’t mean I have to be dressed to the nines (Translation: all poshed up). I think it depends on the occasion and there are times when jeans and cute pumps are more appropriate than a cute dress and killer heels.
My best tg girl friend cant leave the house without full make up. I think we always try to look our best to be passable. We dress up more than dress down to meet the occasion and cover imperfections.
When noticing the average girl when Im out and about is rather disapointing. They rarely look that good, in my opinion, and dont make much of an attempt to do so. Maybe if we felt more confident in how we looked we would do the same. I’m still inclined to look good when Im dressed no matter what the occasion.
The sign of the times is lazyness and casual dress and I just will not go that direction. I enjoy looking my best.
I’m a GG, and sometimes I dress for comfort and sometimes I dress to look nice. Dressing nice some of the time makes those times nicer, much like some CDers feel I would think. Having to dress up all the time, say for a formal work environment, takes the fun out of it.
My question, and I am sure it has been asked before, is for the CDers that prefer to put on a more dressy look. How do you dress in “drab/male” mode? Do you dress as nicely in mens clothes as you do in women’s clothes? How often do you dress nicely vs. comfy in mens clothes?
I think we all could use a little primping. According to my mother, this is what is wrong with the world, people don’t know how to dress properly.
Good question. I know I like looking my best when I dress, but there are times when I just don’t have the time required to get all dressed. At these times, I would wear a simple denim skirt, tights and a t-shit (a women’s T for sure) along with simple flats or sandals. other times it might be a jumper with a button-down shirt. But, I would always be in something feminine. I leave the “bummy”look to my male self. Though I have only been out in the real world a few times dressed, I’ve always dressed in a more feminine, though conservative and casual style. I do hope that one day I will be able to go out into the world dressed in a beautiful evening gown or a very chic outfit at least, but not to just go and pick up the mail. True, many women dress way to casual, but there are many out there who do dress more femininely, young and old and I like to consider myself one of them.
My best tg girl friend cant leave the house without full make up. I think we always try to look our best to be passable. We dress up more than dress down to meet the occasion and cover imperfections. When noticing the average girl when Im out and about is rather disapointing. They rarely look that good, in my opinion, and dont make much of an attempt to do so. Maybe if we felt more confident in how we looked we would do the same. I’m still inclined to look good when Im dressed no matter what the occasion. The sign of the times is lazyness and casual dress and I just will not go that direction. I enjoy looking my best.
+1
I think dressing nice is a good way to go but I don’t have time for it.
I vote for casual but usually with a skirt.
I’m usually pretty casual with how I dress but that’s because I haven’t made a GG friend that I trust enough to teach me how to do makeup and the money to afford to experiment. I am in the process of making a really good friend at Naropa before I leave for Metropolitan State College of Denver.