Pragmatic Crossdressing: Getting out the door more easily

Following on from my previous blog post, I wanted to talk a little about making dressing up and getting out there a bit easier. The number of days where I had decided I was going to dress up, only to end up not doing so, is depressingly large, and each time, there was always some reason why it wasn’t practical to do so.

Fear, I suppose, was one of the biggest hurdles to get over. That’s still a bit of a work-in-progress – each time I dress up, there’s always a little bit of fear, and given the long hiatus, starting again was scarier than I had hoped. Here are some of the numerous reasons (*coughexcusescough*) that prevented me from dressing up earlier:

  • Make-up takes too long
  • Figuring out what to wear takes too long
  • Shaving takes too long
  • Moving all my cards from my wallet to my purse/wristlet takes too long (and is a pain).
  • Moving my laptop out of my backpack and into a different bag is a hassle
  • I just don’t feel like it.

Ok, that last reason is valid. Why would I try to force myself to dress up when I don’t want to? Dressing up is supposed to be an enjoyable experience, not one that you have to convince yourself to do! The rest of them though, you should rightly be taking with a pinch of salt. On the face of them, they seem perfectly reasonable, but I resolved to dig a bit deeper and see if I could find ways to reduce the friction as much as possible to enable me to get out the door quicker. Let’s take a look:

Make-up takes too long, and I’ll be late for work!

Since the baby was born, time is definitely at a premium these days. Precious minutes of my day disappear into the vortex of parenting, and any way I can reduce the amount of time to get ready means more time with the baby, and more opportunity to dress up. Make-up, in particular, was my biggest roadblock. Or so I thought.

I started to wonder… How long did it actually take me to put makeup on? I was pretty convinced that it took me an hour, but that didn’t seem exactly right, so I decided to conduct an experiment. How long would it take me to get full makeup done, if I skipped out on a few things? Did I really need to spend 5 minutes getting my eyeliner-wings right? did I even really need eyeliner? I wear glasses all the time, so you probably wouldn’t see more of the detail – and I could also probably not fuss around too much with trying to achieve complex eyeshadow looks. Sticking to basic eye-shadow, no eyeliner, no lip-penciling trying to get the shape perfect, I managed to get a reasonable look done in 20 mins.

Apologies for vertical-video. I realised my foolish error as soon as I was done. I am the worst!

I could probably save a good five minutes if I wasn’t applying concealer with the tiniest brush in the world. I should probably get one of those makeup sponge-egg dealies.

In any case, too long? I think 20 minutes is a perfectly reasonable amount of time to get makeup done in! Crossdressing-Myth: BUSTED!

I don’t know what to wear, and figuring it out will take too long!

Yes, yes, figuring out what to wear takes some time, but if you’re in a rush, GUESS WHAT: You can do that the night before! At the very least, it’s worth not trying to come up with a whole new combination of your separates on the fly, but instead building up some library of outfits that you know work well together so that you’re not trying to match blouses/skirts/shoes while the clock is ticking down. That, and having some good basics that essentially go with everything really helps towards getting ready quickly! Case in point, I own a…lot… of shoes, but when I’m dressing up for work, I generally settle on one of maybe three options for footwear, because they tend to go with everything!

Shaving takes too long, and I’ll be late for work!

Ok, so shaving my face is definitely necessary. But what about your other parts? Depending on what you decide to wear (which clearly you will have figured out the night before, right?) maybe you won’t need to shave your arms/legs too! I’ve gotten super into leggings recently, which means that I probably don’t have to shave my legs. I’m pretty hairy, so doing a full leg-shave takes up an awful amount of time, but if my legs aren’t going to be visible, I can leave them alone! Last week when I dressed up to work, knowing what outfit I was going to wear, I only had to shave my face, my arms, and a little of my chest – essentially just the skin that was going to be visible.

Another thing that can help is that you probably don’t want to be trying to shave body hair that’s pretty long. Even when I’m not dressing up, I tend to keep my body hair trimmed pretty short – if you have to do a full trim followed by a shave before you start getting dressed, you’re doing something wrong!

AND, you can totally do the trimming the night before, if you know you’re going to be crossdressing the next day.

I have to transfer all my credit cards and cash from my wallet to my purse! ARG!

This always kind of annoyed me, and maybe that’s just me being stubborn, but I decided that if I was going to dress up, I wasn’t going to have a manly wallet while in girl-mode. So in order to get around that, I would transfer my credit cards, cash, ID, badges, etc between my wallet and my wristlet each time I was switching modes. This… was a giant pain.

So I decided… what if I just… didn’t.

There’s two options – I can either keep all of my stuff in my wallet, or keep all of my stuff in my wristlet. I settled on wristlet. I recently upgraded to a newer, and bigger, phone, which didn’t fit into my old wristlet, so I bought a new one, as can be seen below:

It fits my phone, has my cash, and essentially everything I need to go about my day. I use that in both male and female modes. Yes, it’s a bit feminine for guy-mode, but not overly so. And, as it turns out, I don’t care about that. It’s actually come to be a lot more practical than keeping my phone in one pocket, and my wallet in another. Plus, I also got tired of just having things in my pockets all the time, so for me this was a bit of an epic win :D

That said, maybe you can just stick with the same wallet you use in guy mode vs when you’re crossdressed. That’s totally fine too!

Moving my laptop out of my backpack and into a different bag is a hassle

So I have this handbag which I love – you can see it in this terrible picture of me from SFPride 2015

Clearly, that does not hold a laptop. So when going to work, after moving the relevant things from my wallet into my wristlet, I would put my wristlet into this handbag, along with whatever book I might be reading, my keys, and my backup makeup stash in case I need to adjust things throughout the day. And then for my laptop, I would have a separate bag I would carry would bang me annoyingly on the thigh. Yay.

But then I realised, maybe I don’t need to do all of that. Maybe women wear backpacks too? Which is of course, obvious. So I just settled on that. I’ve talked before about paying attention to what women *actually* wear – this instance was a particularly dumb blindspot for me, given that basically all the women I know wear backpacks to work.

In short

The last time I dressed up, There was no transference of items. Everything was already in my backpack from the day before, and everything was already in my wristlet, because I use that all the time. My makeup took 20 mins, and I didn’t have to shave my legs because the outfit that I had already decided on did not require it. I gave myself a good 2 hours to get ready, but it took me so much less time than I expected, that I ended up sitting around for a bit once I was ready, and I still managed to get into work early. Jeez.

It took a little bit of work, and saved me a lot of time, and more than anything, got me dressed and out the door far quicker than ever before. Some of these tips won’t work for everyone but I hope to impart a general sense that you can probably get faster if you want to by looking at your process for getting ready and asking yourself how much of that is really necessary.

Your friend in speedy crossdressing
Liz <3

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