Assuming you’re not wanting to stay at home and cross-dress quietly, it’s usually a good idea to figure out what sort of ‘look’ suits you.
Tarting yourself up before going out isn’t really an impulsive, snap decision to make. After all, you’ve been practising putting on makeup and choosing what to wear, but does it suit you? Are you at all worried that the skirt is too short? Or that you look like a guy in a dress rather than someone more ambiguous or even feminine? Will people stop and stare and ask you, “Dude… what the fuck?”
There’s a lot you can miss looking in the mirror, so you can give yourself permission to take a selfie. Really, it’s OK. Take pictures of yourself standing, sitting, walking about even. The main thing is, when you look at the pictures or movie clips, would you say to yourself, “Dude, what the fuck?” If you would, if you have a niggle in the back of your mind that maybe you shouldn’t go out looking like that, then don’t. Only head out once you’re wearing something you feel works for you. Put your mind at ease as much as possible. If something doesn’t look good, try to figure out why.
For my part, it helped me reject a whole load of skirts, tops and dresses I got from charity shops to see if I could make them work. The one on the left, below, is from my not-quite-ready-to-go-public days. I wore it for a few selfies before realising I hated the colour and style – and that just because something looks good on a mannequin, it doesn’t mean it’d look good on me; picking up basic stuff like this took a bit of trial and error. As for the one on the right, I figured out very quickly that skirt length is important when you’re sitting down…
Looking at selfies also made me hypercritical about my makeup and posture and how much fat I should lose. But it was worth it; by the time I did go out, I was as confident about my appearance as I could be without getting independent feedback.
Now, I’m a vain, loudmouth attention-slut (when I’m in a good mood and things are going well), so I’ve had pictures taken in all sorts of places just so I can have a record of different looks I’ve tried. A lot of these were done really early on summer mornings, or in quiet locations, or sometimes both. The main thing is, there was plenty of time and space to get poses, backgrounds and angles right (or at least, ‘right’ enough, given I was freezing my arse off and didn’t want to completely exhaust my girlfriend’s patience).
The trouble is, taking photos in public can cause problems when there are other people about. If you’re wanting to try something cute, having onlookers can be a bit inhibiting. Worse than that, if you’re on private property (cinemas, shops and the like count as this), people can ask you to leave, which is awkward. Strictly speaking, you need permission to take photos in a shopping centre (for example) because it’s private property. In practice, you can take photos until you’re asked to stop (and security guards *will* ask, because it’s an easy way to demonstrate they’re doing their jobs). They can ask you to leave, or escort you out, but they can’t take your camera, ask to see or delete photos or detain you. You can take photos from the pavement (but not the car park), though.
Personally, I think it’s worth taking pictures when you’re out cross-dressed. Give yourself something to look back on. Give yourself something so you can see how your ‘look’ has developed from the early days. Give yourself a record of something you’ve never done before!