A Quick Guide to 8 Must-Have Items for Any Crossdresser

The beginning of a new journey can always be a bit daunting.  Every crossdresser has their own unique starting point; a different moment or item that sparked an interest in being feminine.

I’ve heard that one of the most common is lingerie; walking through the women’s underwear section of a department store or holding a pair belonging to a loved one.

Something I’ve always struggled with is trying to completely and totally pass as a woman when fully dressed.  It’s one thing to be home alone and slip on some tights or a pair of panties to feel womanlier in private, but completely transforming into my female self takes time, effort, and practice. 

However we dress, be it just a little bit or a full make over, accepting your crossdressing can be difficult.  It is important to be prepared, and understand how to transform yourself to the degree you desire.

When any of us discover our desire to look feminine, we often go out and begin by buying cheaply.  A few panties or bras from Target, maybe a dress from a second-hand shop, or a low-quality wig.  It can be very tough to figure out what we need to make our personal vision of our feminine self a reality.

It was years before I discovered all of the resources online to help crossdressers.  Along with all of those helpful websites; I discovered that there were companies that make products just for the crossdressing community.

 All of this information took a while to take in; in the end I was better prepared for each time I dressed.  Let me try and share some of what I learned about the basic supplies that every crossdresser should have in their inventory.

Having these eight items to hand will make every crossdressers transformation much easier to achieve.

1. Finding your best hairstyles and wig

A wig is a fairly obvious place to start.  Most of us probably keep our hair short; I know I do.  Along with typical male hairstyles, male hairlines are typically farther back than a woman’s and our foreheads have different profiles.

Using a good wig can obscure these less desirable features and accentuate other more desirable ones.  Please read our article about how to choose the best wig for you (insert link to previous article here).

Personally, I like to have long flowing hair when I’m dressed.  I picture myself with lovely long hair that’s slightly wavy.  Having a small selection of wigs at home can allow you to change up your look depending on how you feel in the moment.

If you’re not able to find a reputable shop in your area for wigs, here are a few online retailers that make good quality wigs in a variety of styles.  Generally speaking, when looking for a wig, you get what you pay for and a more expensive wig will last you longer and look far more natural.

Enfemme Style – Enfemme is a crossdressing fashion retailer based in Philadelphia, PA, USA.  They have a good selection of wigs in a range of styles and prices.  There are also a number of wig care items for sale in the wig section of their website.

Roanyer wigs – A good selection of quality wigs.  Most are long haired styles, shoulder length or longer; perfect for those girls who like flowing hair.

2. Covering your beard or stubble

Some of you might be familiar with previous Eurovision champion, Conchita Wurst, who kept her full beard for her drag performances.  I thought this took a lot of guts, and it’s not something that I would consider.

In fact, what to do about my beard is something I’m continuously wrestling with.  My dilemma basically is that I think I look better as a man with a beard and I like having one; but this isn’t compatible with dressing en femme.

I think there are basically two solutions here.  Either shave very closely before each make over, or invest in a mask.  I have chosen the shaving route for financial reasons.  It’s important to not miss a single spot, no matter how small, and to shave from multiple angles.

I will cover my neck with upward and downward strokes.  It’s important to cover every angle to make sure that any hair is cut as far down as possible.  I’ll do this with a triple bladed razor.  Using the right make up and skin care is also quite important.  More on those later.

Masking is another option; Roanyer offers several styles of mask for crossdressers.  If you’re considering investing in a female mask, please feel free to contact us for advice about which would be the best for you.

A female face mask offers the obvious advantages of full coverage of not just your beard, but all your facial features.  Suddenly a high hair line, hairy ears or a short beard aren’t a problem.  Feel free to explore this option; check out our YouTube channel for more information.

3. Getting a feminine waist and shape

Being able to achieve a feminine shape is one of the biggest hang ups and goals of any crossdresser.  I often find myself admiring the hourglass figure of women in the gym and getting jealous.

Being able to shape our male figure into a more feminine one is a high priority for all of us.  There are a few different methods about how to achieve a feminine waistline, but all of them will involve some slimming garment.

All of these fall on a spectrum.  At the less intense end, I’d consider control top pantyhose or a pair of panties with a minimizing waist.  At the extreme end, a full corset. 

In my younger years, I’d combine a few things from the less extreme end of this spectrum to try and get the results I’d like.  Back in those days pulling on a pair of high topped pantyhose would do the job well enough.

As I’ve gotten older and progressed in my dressing, I’ve found that I really value a flat and slim waist combined with female hips. If I’m just having a quiet day in, I might be satisfied with some strong elastic shapewear; something like SPANX.

Any time I’m thinking of going out or doing a photo session, I really need a corset to be happy with the end result.  Nothing else can come close to feminine results of a well fitted corset.

There is one last option to achieve feminine results and that’s a silicone girdle.  Just like a silicone breast plate, a silicone girdle can give the wearer the most dramatic sudden change.

The silicone is often molded to look like a woman’s vagina; some even have space that allows you to be penetrated.  These can be a bit extreme if you’re only looking to gain a girly shape, but if you really want to feel like a woman to the bone, this might be for you.

Elastic shapewear and control top tights and panties are easy enough to find in any department store.  When buying them, I’d encourage you to think about how high it will reach on you.

In order for elastic shapewear to work, everything that needs shaping has to be underneath the shaping garment. Otherwise the results will be less than ideal.

There are a few retailers that specialize in shapewear and corsets for crossdressers.

Glamour Boutique Corsets

A retailer for crossdressers in Northern New Jersey, USA.  Some excellent advice about corsets and a good selection of styles and heights.

Dress Tech

Another online shop specializing in clothes for crossdressers.  A good selection of elastic shapewear.

Roanyer Corsets

Roanyer has a selection of corsets now available.  A good range of style and sizes, priced to fit your budget.

4. Gaining a female bust, Breasts!

Breasts are often at the forefront of every crossdressers mind.  We all are envious of the beauty and sexiness of a woman’s breasts.  Creating the illusion of breasts for us when dressed can be quite difficult.

A lot of us start off stuffing a bra with socks or tissue paper to create volume under a t-shirt, but this doesn’t make for good looking breasts.  There are a great number of items you can use to create more convincing breasts when dressed up.

There are the low budget, do it yourself techniques. Water balloons, tights stuffed with rice or other methods are nice to experiment with in the beginning.  These items can help you figure out your optimal breast size.

Because they are so cheap and disposable, if you get it wrong, it’s easy to try again.  For any crossdresser looking for even slightly realistic looking breasts, these just won’t do.

There are some cheap options for breast forms, usually made of some foam rubber and they can be found on some websites for as little as $30 or $40.

These cheap foam forms will look more natural when worn in a bra and give you a good profile.

There are disadvantages though; they won’t have the weight or feel of natural breasts, which is likely what every crossdresser hopes to have.

Silicone breast forms are by far the best option.  Every serious crossdresser should invest in a pair.  When looking to buy some breast forms there is a lot to consider; size, shape, weight, and coverage.

Breast forms usually come in two shapes, teardrop or triangle.  Teardrop breast forms are the traditional shape, and can often look very similar to a breast implant.  They usually fit well in most any bra.  They will give you a nice line under your bra strap.

The downside is that you risk looking like you have fake silicone implants and not real breasts; most women’s breasts are not a perfect teardrop shape. Triangle shaped forms are likely to give you a more natural looking silhouette.

If you have a broad chest, they will also offer more coverage than a teardrop shape.  The downside here is that unlike a woman’s natural breasts, silicone isn’t as malleable, and it can be difficult to find a traditional bra to hold them.

Pocket bras for these are available, and I would recommend using one if you choose a triangular shaped form.  Either shape will give you the satisfaction of a feminine bust and help you look your best under the right clothes.  A good pair of breast forms is something you’ll find yourself using again and again.

The big disadvantage of breast forms like these is the lack of cleavage and coverage.  Because of that, your wardrobe choices when wearing them can be somewhat limited.  Getting a breast plate, which will fully cover your chest will open up the possibility of wearing low cut tops and having your own cleavage.

Another advantage of a breast plate is that they usually come with a high collar, which will cover your Adams apple and rest just under your jawline.  Choices about plate size, cup size, or skin tone are all up to you.  I think the most important thing to consider when buying a breast plate is the material used to fill the breasts.

I would spend the extra money on a silicone filling.  I owned a silicone filled breast plate and the bounce and natural texture of the breasts was worth the money.  I’ve worn a foam filled breast plate, and while it gives good visual results, the feeling of having a silicone filling was much more satisfying.

A high-quality breast plate will cost you though, so look out for promotions from quality manufacturers. Roanyer sells multiple silicone breast plates.  There are also a number of videos on the Roanyer YouTube channel showing how to use them.

5. Building a Make-up collection

Achieving a feminine face is going to be impossible without a good supply of make-up.  I know how a newbie can feel when looking at all the different cosmetic products available; thinking about it can make me dizzy.  (Here’s a video to help you get started.)

I think it’s fair to say that no one ever stops learning about new make-up or new techniques for applying it.  There are a bunch of articles on our blog to help you learn about building up your collection (here).

When thinking about make-up, I was once really overwhelmed.  Over time, I’ve found that Youtube has a lot of really helpful tutorials do to assist your learning.  These are some videos or channels I really thought were helpful.

Samantha Lux

An American trans Youtuber who does a great make up tutorial in this video.  She also has a number of funny videos commenting on current events.

BBC The Social Tutorial

This video has some very clear instructions to follow and basic techniques to learn.  It also fits my face shape quite well.

Casey Blake

This whole channel has lots of content related to make up, fashion, and support.  There are simple tutorials for a quick everyday look as well as more involved tutorials for looks to use on a special occasion.

When looking for video tutorials online, I’d suggest looking for ones made by transgender women.  Their face shapes and structure are going to be similar to yours.  They will also likely drop in tips about how to feminize some masculine features.

If you are feeling very daring, you can go to a shop and ask for some samples before you buy, or book a full make over.  ULTA Beauty offers services like this and of course products are available for purchase.

There are professional male to female make-up artists who can be booked for transformations (click here).  If you know of any others you’d recommend, leave a note in the comments!

6. Developing a Skin Care Routine

A skin care routine is something that women love to talk about.  Everyone has their own method.  An ideal skincare routine can make you look younger, more vibrant, and feminine.

I’m sure these are all things that we’d like to be able to achieve.  There are a few basic things to learn when thinking about your routine; we’ve got some very good information for a beginner here.

Once you’ve got the basics down you can start to experiment and individualize your routine.  I like to think of my skincare routine as laying the best foundations for any style of make up I want to try.

In addition to keeping your face in prime condition; a good skincare routine will help you feel cleansed and refreshed each morning.  The resulting softer moisturized skin will allow you to feel more womanly every day.

If you have any serious skin issues, such as some persistent acne or eczema, I’d encourage you to seek advice from a dermatologist or other professional before choosing products.

7. Using a gaff to gain a feminine front

A gaff is a specialty garment that helps us tuck away our manly bits to achieve a flat, feminine crotch area when dressed.  Gaffs are really essential for any serious crossdresser.

Everyone has a different strategy for tucking back their bits when we start out crossdressing.  I think the classic method is to just double up on some tight panties and to do a quick smoothing out before pulling up your underwear.

As things progress, we might move on to shaving and taping; which I’ve always thought was too painful to even consider.  The more I learned, the more I considered most methods to be inadequate for long term tucking.

The main benefit of a gaff is that this is a garment that is designed by its manufacturer to hide your manly bits comfortably and effectively.  Some gaffs are just compression garments that won’t require a full tuck, but just keep things snug against your body.

Others come with tighter fits and are designed to make use of your inguinal canals to hide your testicles in the most effective place possible.  If you didn’t know about your inguinal canals, I strongly suggest learning about them & practice finding them.

Some gaffs will even come with an insert to give the illusion of a feminine slit on the front of your panties.

Gaffs can come in many styles, shapes and sizes.  Generally, the most common styles are thongs and briefs.  Anyone who is familiar with the pros and cons of these styles of panties; consider those when purchasing a gaff.

Basically, if you value sexiness and looks over long term comfort, choose a thong-backed gaff.  If you want your gaff to sit comfortably for a longer period of time, choose a gaff in a brief style.

Because of the function of the gaff, a brief will be more comfortable over the long term because the tension needed to maintain your flat front will be spread out.

If you’re interested in buying a gaff, Origami Customs makes some excellent products in a range of styles.  Their website offer has come great guidance about sizing and the best style for you.

Roanyer also has a selection of Gaffs and girdles which will help you flatten your front.  Find them here.  Roanyer girdles can also help you achieve a flat front and more!

8. Indulging in women’s shoes

Nearly every woman I’ve known goes nuts for shoes.  A past partner of mine once took a job in a shoe shop just for the free shoes. Needless to say, we soon had boxes piled high in our apartment.

Women’s shoes come with so many more things to consider than normal male shoes.  When I’m choosing shoes in my everyday life, I’m mostly concerned with comfort not looks.

Women’s shoes are a whole other thing entirely.  There are an endless amount of choices.  The best advice I think I can offer here is to always have a few pairs in black in a few different styles.

Black shoes can go with almost any outfit.  Another bit of advice for you is that shoes might be an area where you don’t need to worry about price too much.

If you’re dead set on having your own pair of PRADA heels, then go get them; but simple brands like Marks & Spencer (link to M&S Shoes) (UK) offer a number of choices at reasonable prices. Good finds can also be made at thrift stores or at shops like DSW or Payless (in the USA).

When buying shoes, be aware that sizes are different in every country and sometimes even within the same manufacturer.  US and UK shoe sizes are similar, so always double check; it’s not worth the trouble to trying to fit into a UK size 7 (a US 7.5/8) shoe because you thought it was a US size 7.

European sizes are also different and used in most countries. If you still have confusion about your size, you can read this article.

Also, try to practice walking in women’s shoes before buying.  They do feel very different to walking in Timberland boots or Nike running shoes.  It’s important to be able to gauge your confidence when walking in heels before buying them.  Start with wedges or shorter heels before buying the high stilettos!

I’d never claim to be the most experienced or best crossdresser, but I do think these eight areas are some of the most important to concentrate on when finding your femme self.

Once I’ve covered these bases I’m ready to focus on my outfit or my plans while dressed for the day. Each one of us has different priorities when en femme.  Please share any of yours and any advice by commenting below!