Crossdressing and Subcultures: A Beginner’s Guide to Finding Your Style

When setting out on your journey in crossdressing, it may be hard to know what the first clothes you should buy are. Should you start straight away with dresses? Will they match those boots you wanted to buy? What makeup will then go with the outfit you’ve put together?

There are so many thousands of makeup brands and millions of clothes to choose from now that you have dipped your toe into our world, and it can be difficult to put outfits together that you’re happy with. But it really doesn’t have to be so difficult.

Here, as we will see, subcultures become really handy for us. Subcultures are usually groups of people who may think, act, or dress in a similar way. We should all know the famous ones like Goths, emos, or hipsters. These are extremely useful for us crossdressers as each subculture usually has a set of fashion trends they follow to identify themselves, and we can therefore easily create the cutest outfits based on any subculture we want.

For example, rather than buying dresses, skirts, wigs, makeup, or shoes at random and hoping they will turn into the perfect fit, you get a short breakdown of each subculture with a guide to some wigs, clothes, and makeup styles that suit them.

For this article, I am going to put together a guide for what to buy for three specific subcultures: Goths, Bimbos, and Preps. I chose these three specifically as they each give off a completely different image, and so would be ever more useful to yourselves. So, for each, I will give a brief description of their style and then 4 or 5 things to get yourself if you want to match their looks!

All of the following looks will work with or without shapewear/breast forms, but I heavily suggest that you pick up some yourself, as they will always enhance your female form.

Preps

I thought I would start with the one that may not be the most well-known of the three. Preps is short for preparatory and refers to the type of now old-fashioned school in which boys and girls are sent to prepare, usually, for a more upper-class education. You will find that their style is more formal than the other two subcultures in this article, but don’t let that turn you away from it.

Wigs

If you’re looking for wigs that will work for a Prep style, you want those that are straight and formal. While Preps can have any hair colour there is, a dark brunette works well with this style. Bangs make a cute addition, too. Accessories for wigs can be headbands in muted tones or black clips.

Sometimes it may be nice to go for a wig with soft curls or maybe one in a shoulder-length style. For those longer ones, a high ponytail will work very well with the overall style.

Clothing

Clothing for Preps is formal and almost college-like. You want a loose-fitting white blouse that covers the shoulders, a bonus if it has some adorable puffed out shoulders that can work to hide any broad shoulders. With your blouse, you want to match that with a small pencil or bodycon skirt in any length. Trust me when I say that both a skin-tight knee-length skirt and a thigh-high pencil skirt will work amazingly for you. Colour-wise wise for the skirt, you want a dark navy or another darker shade.

You want to match these with a belt and a set of tights. It is your choice on how dark these tights should be, but as long as they are not darker than your footwear. In terms of footwear, any formal high heel will work wonders here or flats, so you need not worry which you buy. An essential for this look is also a pair of glasses, which may be your real prescription ones or a fake pair from Amazon. I suggest that these are bigger framed ones to make your face appear smaller than it is.

You may also want a cute strippy tie to bring it all together. This is where having a breast form will be key, as you can either have the blouse slightly unbuttoned with your tie barely done up to reveal your chest, or the blouse and tie done up tightly, which will only emphasise your chest’s shape.

Makeup

There is not much to say about the makeup for a Prep, but it’s best to keep it simple. You may want a bold colour to make your lips stick out, but less is more when it comes to pre-op makeup. The only thing I am certain about is the use of a freckle pen for a Prep look. This just gives off an adorable soft autumn look with those big ol’ glasses.

Bimbos

Now, in the past, Bimbo has been used as an insult, but has very much been retaken by those wishing to identify with it. This style looks to emphasise your feminine curves whilst being wrapped in pinks and pastels. This look will almost definitely require shapewear in the form of hip pads, a corset, and breast forms.

Wigs

A Bimbo look will give the most freedom out of the three subcultures in this article. Any styles are more than welcome, but you get extra points for blonde wigs, or if you are worried about your eyebrows not matching blonde, you can also get a blonde wig with black or dark roots to give the effect you bleached it. This is what I do myself.

Clothing

There are so many styles of dresses and skirts, and so on, you can wear to match a Bimbo look, so instead of giving exact examples, I will give you some general tips. First, keep every bright pastel and mainly pink. The second is to keep everything bodycon, so dresses and skirts should cling tightly to your hips and breasts. Third, any length dress works, but it’s key to show that gorgeous soft skin of yours!

Makeup

This is where the Bimo style really shines, as you can do so much that fits the style in terms of makeup. You may already be able to guess this by now, but you want pink, pink, and pink! From a hot pink glitter lipstick to the soft bubblegum eyeshadow and rose pink cheeks, you want to keep it all pink all the time.

Goths

Last but not least, the Goth subculture has to be the most well-known of the three subcultures we’re looking at today. They are famous for their dark looks and are an absolute internet sensation when it comes to gorgeous looks, which have challenged traditional fashion. I mean, we’ve all seen those posts of men looking for their dream Goth gf.

Wigs

In terms of wigs, you want to basically go for the opposite of the Prep. You can go any style/length you want, and it’s encouraged that either a jet black or dark brown is used. (With colourful highlights if you’re wanting an Emo look). Feel free to add any darker accessories to your wig or even a short veil to really maximise that Goth style.

Clothing

Now, interestingly, I am not going to say you just want any dark long dress. At the same time, you may have little wiggle room in terms of colours, as they should absolutely be kept to blacks and extremely dark shades of colours; you don’t necessarily have to go for long flowing dresses. This is because a more recent addition to the wardrobe of the Goth is a pair, or several, of fishnet stockings which would not be seen underneath such thick dresses.

You will now find modern Goths with shorter skirts or dresses which emphasise their legs and fishnets, which can come in a variety of designs. Personally, I find big hole fishnets are best. Along with this, you always want to see if you can add any silver chains or spikes where possible. I suggest getting some fake silver nose/ear piercings to wear with your look.

Makeup

I am sure you are able to guess that for makeup, you want a lot of darker tones. But this is an amazing opportunity to get some striking and dark matte lipsticks, which are challenging to match with any other style other than Goth.

I myself have invested in several matte lipsticks, which only go with my Goth looks and which really make my lips pop. It may be best to experiment with a lighter foundation or concealer to give a more pale look and then compound that with a darker eyeshadow, not only over the eyelids but also under the eyes.

Conclusion

To recap what we have just gone over, this is in no way some kind of “official” guide, and you may absolutely disagree with the points made. I am in no way saying what is or is not “true” Goth looks, etc.

All I really care about is you experimenting with styles and enjoying the discoveries you make. However, I do emphasise the importance of hip pads, corsets, and breast forms for any crossdressing look.

Stay safe out there, sisters, and just enjoy being you.