A Beginner’s Guide to Crossdressing

The question I get asked the most is ‘how do I crossdress?’  Crossdressing is pretty easy and complex at the same time.  You can go as minimal or as far as you want.  Crossdressing can be as simple as slipping on a pair of panties or as in depth as shaving your body, getting a $60 makeover and hitting the town.  It’s really up to you.

Crossdressing takes time, practice, mistakes and money.  It’s about discovering yourself.  It’s about finding what you like, what you are comfortable wearing and uncovering that part of you that might not get out very much.  It takes time and patience.  No one expects the first time they paint something that it will be a masterpiece.  Be easy on yourself the first (or even the one fiftieth) time you dress up or apply makeup.  You might not look as fabulous as you want, but you’re getting there.

Crossdressing is something you learn by doing.

Achieving my look comes down to a few different parts.  My makeup, shaving, and clothes.

Let me first state that I am not speaking for the entire transcommunity.  I am not saying these are the standards and expectations you must meet in order to be trans.  You are transgender if you say you are transgender.  I have seen gorgeous women with facial hair and have met many transwomen who wear jeans and sneakers and no makeup.  The term transgender covers a lot of different ways that one can identify as…genderqueer, bi-gender, crossdressing, agender…the list continues to grow.  What I am writing about here covers some of the basic topics I get asked about shopping, makeup, shaving and going out.

I also want to state that I do not believe in “passing”.  I don’t think I pass, and you likely won’t either.  What is passing?  Who decides if you pass or not?  Who has the right to decide if you look feminine enough?  What does that even mean?  Women, whether trans or cis, all look different.  Some cis-women are tall, have broad shoulders, hands of all sizes and have different facial features.  Holding ourselves to a certain standard means that we have expectations as to what a cis-woman “should” look like.  Here’s the reality:  Some cis-women have large hands.  Some are taller than men.  Some have deep voices.  Some have facial hair.  Does this mean they don’t “pass”?  Of course not.  All cis-women are women (if they choose to identify that way, of course), all transwomen are women, no matter how anyone looks.

“Passing” and loving how you look and feel are two completely different things.  When I walk through a mall wearing my favorite dress and heels I feel *amazing*.  I don’t care what anyone else thinks.  What do I care if someone thinks that I am not beautiful?  What do I care if someone knows that I am transgender?  It doesn’t affect me in the slightest.  You are the only one that gets to decide if you are beautiful.  And you are.

However, I also remember the early days of dressing up, going out and being comfortable.  It was a roller coaster of emotions.  I think all of us go through swings of self-esteem.  I certainly did at first and it still happens from time to time.  It’s normal.  I think what helps me get through them is just accepting and loving myself and not worrying about what other people might think.  Remember, unless you ask them, you’ll never know what they think.

I think sometimes our self-esteem is so tied up in how we feel about how we look.  I think most of us have felt at one time (or one hundred times) that we are not pretty enough, we look too male, we’re too tall, our feet are too big and a million other thoughts.  When we don’t love how we thought we’d look, or how we wanted to look, it can be a little…devastating, to be honest.  The first time I wore makeup and a wig I was amazed at how I looked but also crushed that I didn’t look like Elizabeth Hurley.  The first time I did my own makeup was also a humbling experience.

What changed?  Time passed and as it did, I got better at makeup, I purchased a better wig, I started to dress better and wore clothes that fit.  We all want to be a size 6 and some of us want to buy the tiniest dress at the mall, but wearing a dress and looking good in a dress are two different things.  After years of crossdressing, I was finally coming into my look.  I was happy, and still am.  But my confidence didn’t only come from how I look.  I also accepted who I was and became happier with who I am.  Acceptance can lead to confidence, which leads to happiness.

Look at these two pictures below.  They were taken a little over two years apart from each other.  Two completely different girls, in my opinion.  And it’s more than the look…you can see a huge change in confidence and happiness.

I started to let go of impossible expectations and learned to accept myself and to love myself and be happy with who I am and how I looked.  I stopped trying to pass and focused on what I wanted to wear and learning how to look how I wanted to look.  These days I feel good about…85% of the time I dress up.  If I am not at 100% it’s usually because my foundation is a little off, my eyeliner not perfectly straight or another small reason.  Time and experience and practice pays off.

And really, once you accept that and believe it, going out of the house or even just looking in the mirror becomes a million times easier.  I promise.

Shopping!

Clothes are easy and hard at the same time.  To find clothes that fit, you just need to try them on.  Not sure what dress size you are?  Try on several sizes to find the right fit.  A rule of thumb is going one or two sizes up from your male clothes.  I wear a medium t-shirt in men’s clothes but in women’s tops I wear a extra large, not because I have a tummy but because I have broad shoulders and need tops that can fit them.  Shoes are similar.  I wear a 10 1/2 in men’s, a 12 in women’s.  I have a small waist but broad shoulders which means I can wear a small sized skirt (an 8, for example) but I need a size 12 dress (depending on the material) because I am wider on top than I am in my middle.  Of course, this is very much a rule of thumb as every department store and designer has a different idea about sizing.  More on that in a moment.

Before you go shopping, it’s a good idea to take your measurements.  Find a measuring tape (not the tool kit kind) and take your measurements for different parts of your body:

-Waist measured at your belly button
-Bust measured at nipple height with no forms/padding
-Bust measured at nipple height with forms/padding
-Chest measurement taken just under pectoral muscle (2 to 3 inches below nipple)

-Shoe sizes are typically one to one and a half larger than your male shoe size

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Once you know your measurements, shopping, especially online, becomes easier.  Most shopping websites will give you your size (whether you are a size 14 or an extra large, for example) if you know your measurements.  Note, however, that EVERY clothes maker and EVERY department store is different.  At Dress Barn I am a size 12, at Forever 21 I am a size 16.

It’s complicated.  Everyone’s body is different.  Finding clothes that fit takes time.  Finding clothes that are appropriate for your age and body type takes practice.  You will spend a lot of money making mistakes when you buy clothes.  The only way to find out what will fit is to actually try it on.  Finding the right sized clothes took a long time for me and will take a long time for you.  Good thing shopping is fun!

The hard part is plucking up the courage to try things on in a store.  Luckily the internet exists.  You can shop all you want online, buy things and send them back if they are the wrong size.  It’s a low-risk way to shop.  Many of us start shopping online at crossdresser specific stores such as Glamour Boutique, Xdress, and Suddenly Femme.

Personally I enjoy going to a store to shop.  I think it’s much easier to use a dressing room at a store.  I’ve gone shopping in both male and female modes and I’ve never had a bad experience with a sales clerk.  The rule of thumb is be friendly, chatty, gracious and polite.  Don’t be rude or creepy.  Just don’t.  Sure, you might get an odd look from someone at the store, it happens.  But you’ll get over it.  It gets easier the more you do it.  And trust me, you aren’t the first or the last man they’ve seen trying on a dress.  If you’re not comfortable there, leave.  Go somewhere else.  I’ve had amazing shopping experiences with super friendly sales clerks who’ve helped me and I know you will too as long as you are a gentleman (or a lady).

Makeup!

Let’s get to another part of my look: makeup.  Makeup is hard.  No one learns makeup on their own.

These two photos are examples of me doing my own makeup and were taken about two years from each other.  There is a world of difference between them.  I am happy with my makeup and I am confident in my technique.

How did this happen?  Time, practice, mistakes and money.

Earlier I said that no one creates a masterpiece the first time they paint.  Nor will they the fiftieth time they paint.  It took YEARS until I was happy with my look.  It took a lot of practice.  I made a lot of mistakes.  I spent a lot of money.  Again, crossdressing is learning by doing.

duringSo, here’s how you learn makeup.  You could watch youtube videos and learn from them but like buying clothes, everyone is different.  Everyone has different skin, different color, different tone.  What works for me might not work for you.  The easiest way to learn makeup is to have someone teach you.

I am lucky to be married to my wife for many reasons.  In my early days she taught me makeup.  She is a trained cosmetologist and knew what tones and shades would work for my skin.  I know not everyone is married to a makeup artist, but you can still learn.  Makeup is hard to get right.  There are still times when my eyeliner doesn’t look good or my color correcting is a little off.  The best way to learn makeup is to schedule a makeover.  I know that sounds like the scariest thing in the world, and it is, but it’s the best way to start mastering your look.  Go to the experts, they will show you which products to use, which tones are best for your skin color and they will teach you how to apply makeup.  I’ve been doing my makeup for years and I probably had ten makeovers in the last twelve months and I still learn something new each time.  ULTA and MAC are where I would recommend starting out.  Remember, you aren’t the first or last crossdresser your makeup artist will ever have.  They are trained to help girls like us.  Makeup artists are also trained with the newest techniques, like contouring, which totally changed my life.

Like clothes, makeup can be confusing as every cosmetic company has different products and shades.  Foundation from Smashbox is different than foundation from Too Faced.  Try different products, try different shades, mix it up, ask for help and see what works for you.  There are no rules with makeup, just do what works for you.  I use a lot of different products from different makeup companies and my foundation/color correcting technique is something I developed on my own.  I started to experiment with different blends and techniques and I finally found a way to completely cover up my beard line.

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Makeup is expensive, so be prepared for that.  You get what you pay for when it comes to cosmetics.  One of my foundations costs $45, another is $6.  I wish the $6 foundation was all I needed, but with my skin type and facial hair, I need the better coverage the expensive foundation provides.  When starting out, I recommend buying inexpensive makeup to get the hang of it.  It’s better to practice with $8 eyeliner instead of $32 eyeliner.  Drawing that perfect line on your waterline takes a lot of practice and you’ll have so many smudges you’ll look like a raccoon.  That’s okay.  Wash it off, and practice again.  Don’t get frustrated.  Makeup removal wipes are essential.

It’s also important to have realistic expectations in both your clothes and your makeup.  You will likely not look like what you expected.  The first time I had a makeover I was hoping I’d look like Nicole Kidman.  I didn’t.  I never will.  Clothes and makeup are magical.  You will look different than what you expected.  You might be disappointed that you don’t look like a fashion model but no one looks like them.

Shaving!

414The first thing I thought before I started to shave my legs, chest and arms was what will people think?  I realized that I didn’t care.  I also don’t know what people think because I’ve never asked them.

Anytime you change something about yourself, you run the risk of someone saying something about it.  My suggestion is to be prepared for it and have an answer ready.  Don’t make it a big deal, because if you do, they might as well.  When I started to shave my legs, I braced myself for questions or comments.  Luckily most people know I am an avid runner and cyclist and shaving your legs is pretty common.  My standard response though is that I hate body hair.  But in all honesty, no one has ever said anything about my legs, arms or chest.

Think about it like this.  If you saw someone with shaved legs, would you say something?  You probably wouldn’t.

But how I shave and do hair removal is how I do it.  You may find a different techniques that work.  Again, I learned how to do this by doing.  I’ve changed my techniques over the years but I think I’ve found a system that works.

Once you shave your legs (or arms, or chest, or…) you’ll never go back.  Smooth, hairless legs feel amazing against bed sheets and a nightgown and a skirt…you’ll be in heaven.
But like anything wonderful, it takes a little work, practice and patience.  The first time you shave your legs will probably take a while and you’ll get a few nicks and cuts and you might get a little frustrated.  But with practice and time, your legs will look and feel smooth and amazing!

The first thing you’ll want to do is use an electric clipper to remove as much leg hair as possible.  You don’t want to get toooo close to your skin but you likely have years of growth and a clipper will make your life easier the first time you shave your legs.  Once you have clipped, you’re ready to get shaving.  The right razor and shaving cream is essential.  However, this is also a matter of preference.  Like makeup, this is learning by doing, in a way.  Some girls use “girl’s” razors, some use “boy’s” razors.  The argument is that boy’s razors are cheaper and get a closer feel.  Some argue that girl’s razors are better suited for the curves of a leg.  It’s up to you but try multiple options.  But whatever you use, use a different razor for your legs than you use for your face and rinse your razor often as you shave.

416I would also recommend taking a bath the first time you shave your legs.  Shaving a leg might look easier than shaving your face but your legs have different curves and harder to reach places than you’d think.  It’s difficult to get every hair on the back of your thigh and around your ankle, for example.  Being in a bath will give you time to sit, to relax and learn your legs.  Also, the warm water will help you open your pores and help you get a closer and smoother shave.  After I got used to shaving my legs I started to shave standing up in the shower.  Again, the first time you do it this way will also take time (and likely the hot water will run out before you are done) and you’ll learn that your body can twist and bend in many new ways as you shave.  You’ll find yourself holding onto the shower bar for balance and stability as you twist and rotate to get every hair.

Patience is key here.  The first time you shave your legs will take FOREVER.  Don’t rush.  As you shave any part of yourself you’ll get better as time passes.  So take your time and savor this experience.

In terms of technique, I start with my upper front thigh.  I use shaving cream (again, try different kinds) and slowly and carefully shave this part of my leg.  Shaving your leg is a little similar to say, shaving your neck and face.  Slow and smooth is key here.  I tend to use long strokes on the longer parts of my leg, and quick, short strokes around my knees and ankles.  But again, whatever works for you.  This is learning by doing.  I then move to the back of my thigh.  The backs of my legs are tricky.  Since I have dark hair and prefer nude stockings, I need to have a close shave in order to look my best.  Before I step into the shower, I do cover the backs of my thighs and lower leg with Veet.  Veet is similar to Nair.  Once I step into the shower, I wash off the Veet and then shave where the Veet was.  This is extra work but it helps with a smoother and cleaner leg.  Shaving the back of your thigh will have you thinking that you should’ve stretched before getting into the shower as you’ll be  bending, twisting and trying to get every hair.  Please hold onto something for balance.

Once my thigh is done, I move onto my knee and lower leg.  Knees are trickier than you think.  The lower leg is pretty straight forward though but the back is also tricky.  I finish the leg with my feet and toes (groooosssss) and then move onto my other leg.

Once I am done, I shut off the water and give my legs another look and then touch up any spots I missed.  The first few times you shave you’ll likely get a few cuts, so prepare for that.  Once you have a smooth and clean leg, you’ll definitely want to use a moisturizer.

Again, the first time you shave your legs might be discouraging and frustrating but like applying eyeliner, it’s something you’ll get better at with time, patience and practice.

If you want to shave your bikini area, you’ll want to use baby oil instead of shaving cream.  Baby oil will leave your skin less irritated and will help you avoid the little red bump thing.    Using baby oil will require you to rinse your razor a LOT more often than using shaving cream, though, but your skin will thank you.  Shaving this area, as you might imagine, takes a lot more patience and time.

When it comes to my eyebrows, I make sure I have them done about every three weeks.  This is probably the most common area one waxes, but I actually have my eyebrows threaded.   It is not without it’s discomforts but also quick, affordable and convenient.

I have thick, black hair…and that goes the same for my face.  We can only shave our face so close and I’m always conscious my beard line being visible when I go out.  Again, this is what I do, everyone’s skin is different and your techniques may vary but there are a few steps I do to eliminate this problem.  First, shave your face as close and as smooth as possible.  Once your face is shaved, use a moisturizer once you are happy with your shaving.  Let the moisturizer settle and then use a foundation primer before your foundation.  This helps keep your foundation lasting longer.  A primer is a must in the days when I am out and about for hours and hours…I don’t want any facial hair poking through.  After I add my primer, I will then apply a bright red lipstick (a little goes a long way!) to my beard line.  This is a method that takes some practice but adding a reddish tint to your face counteracts with the slight blueish tint facial hair can create.  Basically what I do is take a very red lipstick and apply a little to my fingers.  I will then spread that to lightly cover my jawline, neck and around my mouth.  If applied correctly you will appear to have a slightly red beard.  Once that is applied, then I will start my foundation.  Please note that this is a tricky process and will likely take a lot of trail and error before you get it right.  Your skin color and foundation shade will likely play a factor in this process.  Don’t be surprised…or discouraged if you have a slightly orangish tint the first few times you try this.  You can also try RCMA Beard Cover, a popular method for those on the stage.

Stepping out into the real world

Okay, so you’re all dolled up and nowhere to go?  Tired of hanging out in the living room?  Hit the town!  Yes, I know, that is scary.  It was scary the first fifty times I went out but it gets easier each time.  Before you go out, please make sure you are ready.  Before I go out, I always make sure my purse has:

-Eyeliner

-Lipstick

-Finishing powder

-Mascara

That’s the fun stuff.  The reality is that I have a lot more in my purse than makeup.  I recommend every t-girl have the following in their purse:

-Cash.  This is pretty obvious but I use cash for everything when I go out.  If I want to get a coffee or need to pay for parking, I use cash.  I like cash because I don’t run the risk of turning over my credit card (with my male name) to a cashier.  I also bring my debit and credit card just in case.

-Proof of car insurance.  If you get into an accident or get pulled over, you’ll need to provide proof of insurance.  Simple enough but plan for the worst.

-Fully charged cell phone.  Pretty self-explanatory.  You’ll need it in case of emergency.  Any emergency.

-Roadside assistance information.  You need to know who to contact if you get a flat tire.  Sure, I can change a tire myself, but no way I am doing that in a dress or heels.

-Driver’s license.  Again, if you get pulled over…

-Spare car key.  If you’re not used to carrying a purse, you might forget to place your keys in it.  A spare key tucked in your purse saves a call to a locksmith.

-Medical insurance card.  Again, plan for the worst.

-A friend.  I don’t mean bring a friend with you, though shopping is a lot more fun if you do, but if you’re out to anyone in your life, drop them a message to let them know you’re stepping out.  It’s good to let someone know you’re out on the town in case you need help.

-I would also recommend downloading the Uber or Lyft app.  If you run into car troubles and need help, having this on your phone can be a lifesaver.  I have an app on my phone and I have multiple accounts associated with it.  One for my male life, one for Hannah.  I’ve used Uber as both genders and I’ve never had an issue.

Where should you go?

Anywhere you want, but plan ahead.  Is there a GLBT friendly coffee shop in town?  Maybe start there.  Or a GLBT bar?  That’s another option.  For your first time out, some of us go someplace where they’re used to seeing girls like us.  It’s important to get used to being out in public and it’s easier if you know you’re not the first t-girl, or the only t-girl there.  If there’s not a place like that in your area, I bet there’s a PFLAG or a Tri-Ess chapter that meets near you.

Being comfortable out will take time but you will get there.  I never thought I’d go to a restaurant or a mall or a gas station in heels, but I do it all the time.

Not comfortable yet in your area?  Drive to a bigger city.  Get a hotel room there, have an adventure!  Bigger cities tend to be more liberal and open minded than smaller towns.  When I go to downtown Minneapolis, I walk down the street confident in knowing I am not the first or last transgirl to strut that street that day.  Bigger cities have seen girls like us before.

Will people see you?  Of course they will.  You’re out in public.  Will they point?  Will they laugh?  Will they whisper behind your back?  Maybe.  But really, so what?  I go out all the time and very, very rarely does anything like that happen.  And the more often I go out, the less I notice it.  Will people recognize you?  Maybe.  If you’re afraid of that happening, again, go to a different town.

I know I was nervous people would point and snicker while I was out in the real world, but that hasn’t really happened to me.  I’ve interacted with everyone from baristas to shop clerks to gas station employees to waiters and I’ve never had a bad experience.  No one has been rude or laughed or anything.  The world is a wonderful place sometimes.

Safety is the number one concern, of course.  I know what parts of my city are safer and I’m sure you do too so don’t go there.  Go somewhere where you can park in a well lit area as well.  Going out for the first time is nerve wracking enough but going someplace a little iffy is just adding more stress that you don’t need.