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HANNAH MCKNIGHT
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https://hannahmcknight.org/a-beginners-guide-to-crossdressing/ 1/20
28/3/2021 A Beginner’s Guide to Crossdressing – Hannah McKnight
What I think people are really wanting to know is that they want to look a certain way but
are unsure of how to do so. There is a look they want to achieve but they are uncertain
about the practical part (how do I determine my size or wear makeup) or the psychological
part (how do I accept myself).
Achieving your look 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 fiftieth) time you dress up or apply makeup. You might not
look as fabulous as you want, but you’re getting there.
This 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 cis-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. Passing is
impossible and isn’t real, but loving yourself is. 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? I am transgender. To me it’s the same thing as someone knowing I am right-
handed. It doesn’t affect me in the slightest. You are the only one that gets to decide if
you are beautiful. And you are.
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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.
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28/3/2021 A Beginner’s Guide to Crossdressing – Hannah McKnight
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
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-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
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 En 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.
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https://hannahmcknight.org/a-beginners-guide-to-crossdressing/ 6/20
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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, you are learning by
doing.
So, here’s how you learn makeup. You could watch
durante
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
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28/3/2021 A Beginner’s Guide to Crossdressing – Hannah McKnight
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.
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!
The 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.
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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
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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.
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-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 LGBTQIA friendly coffee shop in town?
Maybe start there. Or a LGBTQIA bar? That’s another option. For your first time out,
some of us go someplace where they’re used to seeing girls like us. You might google
‘crossdresser friendly stores’ but it’s not likely you will find anything. 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.
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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.
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