Dressing up for different occasions as a crossdresser

Crossdressing doesn’t need to be limited to your house, or any kind of closed quarters. It's a way to express yourself, so with some confidence you should be able to crossdress on any occasion that you want, as long as you are comfortable with it and dress up accordingly in an appropriate manner. Of course, coming out as a crossdresser or trans person helps a lot in terms of presenting yourself publicly dressed up, but common sense about clothing is pretty much essential for you to be able to avoid stares or unwanted attention in general. Passability, however, while desirable and wanted for many crossdressers, is something pretty much optional and ambigue, so here we’ll be focusing on the outfits in general, and how to properly choose them for each occasion in which you want to crossdress at. 

1- The basics: Dressing up at home

Well, I've decided to start here mainly because it’s the easiest part, and an opportunity to practice what you’ll do outside. Crossdressing at home is basically the “creative mode” of crossdressing, allowing you to try out whatever you want to dress before you do so publicly. Any outfit can go here, from the most formal ones, to the more intimate and sexy looks with lingeries or elaborate cleavages. Makeup is also up to you, not necessary unless you want to pass even at home. But if you plan to spend your day in womens clothes just for the feeling of it, i would recommend going for more casual and comfortable outfits, as well as avoiding shapewear with too much compression, as it allows you to keep your looks for a longer time than you would if you had to endure something uncomfortable. As for the outfit itself, you could pretty much use just some pretty underwear to maximize both the comfort and feeling of femininity, but some other options with more “coverage” are camisoles, pajamas and sweatpants.

2- According to the weather

Well, the thing here is to adapt your outfit for the weather and climate of the occasion, so the applicability of certain garments might depend on your country or region. Let's start with hot weather, as it's more common during this time of the year. In this case, you’ll probably want to apply moderate amounts of makeup, since it could melt off if applied excessively, ruining all your work. In terms of outfit, go for something light, such as a light colored dress or a tank top and a skirt. Depending on the thickness of your pantyhoses, you could use them to get an extra-enhancement of your leg’s silhouette, but I would recommend changing them for knee high socks, or even shaving, for a higher level of comfort and increase in your self-esteem. Also, shaving your legs might refresh them and help you with the heat. Regarding shapewear, keep in mind that warm weather is ideal to wear more revealing outfits, and if you plan to do so, get a silicone bodysuit to conceal it or avoid shapewear in general. If you go for the first option, make sure to watch out for the compression and comfort, ensuring that you don't get too tired from enduring it.

For colder weather, you can get really creative, as you’ll be able to use a larger amount of outfits. Even if you can't wear something too revealing, a silicone breastplate can grant you a stunning cleavage, and more robust types of shapewear, alongside some paddings, can grant you a silhouette curvy enough to compensate for the volume of the clothes, while Leggings will do wonders to highlight and feminize your legs. As most of your body will be covered, you wont need to bother shaving as well.

3- Dressing up as a woman to work (and other formal occasions)

This kind of situation can be a really delicate topic, since crossdressing can be some sort of taboo, depending on your workplace. Before anything, talk to your boss or to HR in advance, and make sure you are in a LGBTQIA+ friendly environment. It is better than suddenly showing up to work presenting as a different gender, as it could create some sort of unrest and surprise. Also, depending on how well you pass,you might be unrecognizable and be mistaken for an outsider in your office, so it would be great to carry some ID and inform your superiors. 

Make sure to choose an outfit that fits your job, and avoid inappropriate stuff. using bodysuits and breastplates to enhance your silhouette is ok, but be moderate on your cleavage and avoid anything too revealing. Shapewear shouldn't be too robust, it's better to choose something comfortable and easy to conceal underneath your clothes, and it would be wise to choose a practical wig, because you don't want to walk around dropping hair all around, or getting it stuck in places that could ruin your precious wig. Heels are good on formal occasions, but if you don't have too much practice with them, go for some flats or non-heeled boots. Dresses and formal shirts are both ok, so it's up to you and your personal preferences.

4- Hanging out with friends 

These moments are meant for you to socialize and have fun, but your outfit should also fit the place you are going to. If you and your friends plan to hang out at a mall or a pub, dress in a pretty way, with outfits as revealing as you are comfortable with. Be creative with the makeup, experimenting with some vibrant colors or even a more gothic look, with opposing tones of black and white. It's your time to shine, so don't be afraid to express yourself the way you want. Use the shapewear of your preference, but I recommend finding a balance between compression and comfort, so you’ll be able to look as curvy as possible for the longest amount of time.

In pool parties and beaches, the best you can do is to combine your shapewear with a silicone bodysuit, and a bikini or swimsuit of your preference. Try to avoid diving though, as it can compromise both your makeup and your wig, depending on it’s quality. A workaround would be to choose a synthetic wig (not your favorite or more expensive ones), and wash it immediatly after you get out, so chlorine won't damage it. For the makeup, try waterproof ones, but make sure you have some makeup remover around if anything goes wrong.

Written by Elise Wren