So I’ve been getting a lot of people asking a variety of questions over the last few weeks; I’ve posted some on here and others have been direct messages. A lot of them, while different, all seem to follow a theme; tell me if you can spot it:
- ‘What would you recommend when going out dressed up?’
- ‘Everything is uncomfortable, what should I wear?’
- ‘Should approach my partner/friends about crossdressing?’
Spotted it yet? All of these questions are, at their basic form, about being comfortable as a crossdresser.
During every crossdresser’s life, they’re going to fell uncomfortable; this could be either physically, mentally, or both. I’ve felt it, you’ve probably felt it, everyone feels it.
Is it because crossdressing is something that’s seen as unnatural? As though you’re doing something taboo or forbidden?
Let’s be realistic for a second here. We’re living in an age where fashion saw the boundaries of ‘normality’ and waved while they went sprinting right past; a man in a dress, no matter how feminine or masculine they look, is nothing surprising any more.
I’m gonna try not to sound like a bitch here, but it’s not them, it’s you.
So Why Am I Uncomfortable When Dressing Up?
1. Because That Dress Ain’t Right On You
I’ve said this so many times before, but I’m gaining hundreds of followers every week so I’ll say it again for all you newcomers (Hi there by the way).
Dress for your body, not what you want your body to be.
Dresses aren’t magical; they don’t just magically give you curves and hide your shoulders. If you’re going to wear a tight dress that starts just above the cleavage and stops just under the hips, you better make sure you’ve got the body to support it (go look at @abbycatsuk, she’s a perfect example of how this look can be pulled off).
Certain looks (like the short, tight dress one) is such a hard look for crossdressers; even experienced gurls, myself included, have difficulty making it work. It isn’t because you’re not good at crossdressing, it’s because these dresses aren’t made for everyone. There are a lot of actual girls out there that would struggle to wear something like that.
Instead, you should wear something that compliments your body type. @isabelladecarrington has made several great posts about this and, quite frankly, puts it much better than I could. It’s worth reading her work if you want to know how you can dress for a more feminine figure.
If you’re after the TL;DR version, don’t wear something short that will cling to your body unless you’re 100% confident it will work. Instead, try a skater dress, I’m yet to meet a gurl who doesn’t look natural in one.
2. Because you’re hiding something.
I’ve struggled a lot with this. Not just with my current partner but previous girlfriends and even friends. Hiding as a crossdresser, for some people, isn’t a choice but a necessity. However, for others, we hide it simply because we’re nervous of the reactions from those close to us.
When I told my friends I knew there wouldn’t be a negative reaction. I realised later that I struggled to tell them because I had made it into a big deal in my head.
This made me extremely uncomfortable. Any time we met where fashion or makeup was talked about, I felt like I couldn’t join in because I would out myself. At the same time I wanted my friends to know, but I felt I couldn’t tell them only because I had kept it hidden.
It felt like a bigger problem than it should have been because I had kept it a secret for so long…
Unsurprisingly, there’s an easy way around this.
If you feel uncomfortable around people because they don’t you crossdress, just tell them.
So many people don’t really care about it these days. In fact, in a lot of circles, it’s finally getting accepted as something that is simply a hobby, no different to collecting stamps or gardening.
The benefit to this; my friends ask me about Jess all the time. I get asked on a regular basis whether I’ll be going to social events as Jess or not, and sometimes Jess has even been requested to make an appearance.
This might not be a problem if you crossdress as a fetish, but for those of you who feel crossdressing is a part of who you are, it’s certainly worth a try. Worse case scenario, you find out who your real friends are.
3. Because you think people are staring at you.
Let me tell you about the first time I went out as Jess. I was wearing 6-inch platform heels and towered over practically everything and everyone in London (I was asked to change the batteries on Big Ben, I politely declined). I like to think that everything else looked on-point, but being that tall made me stand out.
I got a lot of stares from people when I first left the car, especially from an elderly drunken gentleman who couldn’t figure out if I was a man or an Amazonian. I had a few wolf-whistles and several sexual comments (probably out of jest, but I’ll take it regardless).
After a couple of minutes, I completely forgot I was even wearing a dress.
Confidence can really help here, and I can’t express how much better it was to be surrounded by friends at this point, but after not very long I stopped thinking about everyone else and just how happy I was to be out. People might have still been staring, but I was no longer caring.
The upside of this is that I only got compliments, not insults (to my face at least). Several people came to tell me about how they loved my outfit, some asked about my heeled boots and several people were shocked when they heard my voice and had simply assumed I was just hella tall.
The thing is, the people who don’t like it won’t make themselves known. The people who like/love it will go out of their way to let you know. The first step is the hardest, the rest is just a cat-walk.
Yeah… I’ve gone and dragged this on again haven’t I.
For those of you who are curious, I’m still contemplating starting the Crossdressing Magazine. I didn’t get as many responses as I wanted but it’s clear that it’s something many of you are interested in.
Regardless, here’s a picture for those of you had the patience to read through this essay of a post (much appreciated).
Yep, those are the tower boots.
I’m going to post a photoset of this outfit tomorrow, so keep your eyes peeled for that. Until then, thanks for reading! I hope this has helped a few of you.
If it has, make sure you reblog for your followers too!