In-Between: A Beginner’s Guide to Crossdressing

mock book cover

Hi girls!

I think I’m getting close to finishing ‘In-Between‘.  I am editing and writing as I go and I’m excited to finish it.  I have a couple more chapters to go as well as some introductiony/biography stuff after that.

As I get close to completing the first draft, I am getting a better sense as to what else needs to be included.  I never meant for this book to be a “how to crossdress” guide, but I am starting to think that a couple of chapters dedicated to some basic techniques on shopping and makeup might not be a bad thing.

I decided to write two chapters for the beginning of the book and I am providing the first of these two chapters below.  I’d love to know what you think!

Love, Hannah

When I was in my late teens, I sought out as many resources as I could when it came to crossdressing.  I was encouraged by how much, if you knew where to look, material was out there. I found autobiographies of those whose dressed like I did, makeup and style guides, forums to help foster a community and more.

When I started my current website, I included a section called ‘A Beginner’s Guide to Crossdressing’.  I did this for two reasons. This first reason is because ‘how to crossdress’ was one of the most common and consistent phrases people used to find my site.  I thought by including a part of the website to this I could spread my… message, if you will, about what I thought crossdressing was, and, in a way, attempt to normalize it.

In my quest to find as much as I could about crossdressing in my younger days, it wasn’t hard to find material that presented crossdressing as a fetish.  I stumbled upon more photos of dudes wearing panties that did not fit than I can ever forget. It was frustrating seeing crossdressers being overwhelmingly represented like this.

This is not who I was.  If there was an audience out there willing to listen, then I should share my thoughts about what crossdressing was, and about who we are.  Not all of us are fetishsts. Not all of us want to post pictures of ourselves in lingerie online. I wanted to be a reassuring voice to those wives that discovered their husbands wore panties and were looking for some perspective.

The second reason I included this was because I received dozens of emails a week from people asking me how to crossdress.  It got a little exhausting. Over time the temptation to respond to these emails in a snarky way grew to the point where I almost responded with ‘buy some panties, ta-da, you’re a crossdresser’ but that would simply be bitchy.  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.

However, that’s not what they really wanted to know.  My belief is that crossdressing is simply wearing clothes that are typically associated with another gender.  I think most people who were asking understood that if someone wanted to crossdress, they just needed to buy a dress or wear eyeliner.  I think what they were really asking is:


“How do I reconcile the part of me that wants to wear beautiful clothes but I’m a guy?”

“How do I find a pair of heels that fit?”

“How do I gather the courage to shop for a skirt in guy mode?”

“How do I learn how to do my own makeup?”

“How do I accept that despite a $70 makeover that I don’t look like Angelina Jolie?”


My website, and my book, is intended to help with accepting yourself.

It’s intended to help you shop for clothes that fit.

It’s about living in a world that doesn’t understand us.

It’s a resource to guide someone through the wonderful world of makeup.

It’s to help with overcoming dysphoria and shattering the expectation of ‘passing’.


There are a ton of books and websites out there about being who we are.  I felt I had a unique and underrepresented voice and perspective when it comes to crossdressing.  I didn’t want to add another book or blog that didn’t say anything new. As I got older, I still sought out books and other resources and saw a lot of designers who sold makeup for men and dresses for crossdressers.  There’s a lot that you can find out there and I am so happy that there are those that design clothes with us in mind. I have had wonderful partnerships with many of these businesses and designers whether it was modeling or writing articles for their websites.

But I realized that I didn’t need to Google ‘makeup for men’ to find a foundation to cover my beard line.  I shifted my search terms to things like ‘makeup to cover facial hair’. I was able to find products that did the trick that cost less than what I was previously buying.  I didn’t need to search for ‘clothes for crossdressers’. When I did that I usually found dresses that were a little on the fetishy side of the closet. Not that there’s anything wrong with that, God knows I have my share of dresses like that.

What I searched for instead were things like ‘dresses for broad shoulders’ or ‘high heels in size 12’.  I found a lot more options than doing it this way. This revelation reminded me that everyone has a body and what we need for them is not necessarily limited to gender.  Many ciswomen wear heels that are sized 12 and up Many ciswomen buy makeup and clothes to minimize or enhance certain physical features.

When it comes to the practical side of buying clothes that fit you, this is the approach I recommend.  You don’t have to Google “high heels for men” for a pair of cute pumps. If you know your measurements, then you can find (practically) anything.

My website is about resources and accepting yourself.  There’s a fair part of creating yourself, too. When I started to wear makeup, I wanted to look like Selena Gomez or Sandra Bullock or _______________.  I was devastated when I didn’t. But as time passed I learned that I would never look like them, I would always look like me. I learned that there was no such thing as passing.  I learned how to shake off dysphoria, I accepted who I was and embraced how I looked. Things that I wish I accepted years earlier.

But these things I learned over time.  They were learned from experience and these epiphanies came with time.  No one could have taught me these things, I had to learn them myself. I think we all did.

This book was never meant to be a how-to guide to crossdressing.  It still isn’t. However, I started to think that a book about living between gender identities almost requires a bit of a practical guide.  I resisted this section for a long time because my core belief is that there is no correct way to be a girl. There is no standard one must meet, no one is too tall to be feminine, no one has shoulders too broad to be pretty.  Providing instructions on how to “look like a girl” seems to be contrast with the purpose of the book and my website.

But here it is anyway.

Let me clarify 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 or present or identify as a girl.  You are transgender if you say you are transgender. You are a woman if you say you are. I have seen gorgeous women with facial hair and have met many transwomen who wear jeans and sneakers and no makeup.

I chose the topics based on the most commonly asked questions I received over the years, such as shaving, learning makeup, and finding your proper measurements.  Looking over these subjects, it all comes across as very practical which isn’t a bad thing. There’s nothing wrong with wanting to look a certain way. My approach to… all of this comes from an insanely high level of confidence and plenty of I Don’t Care What You Think.

However, if I am being honest, this attitude came from loving how I looked.  I love how I look in a cute dress. I love how I look after I do my makeup. Loving how I looked came from practice with makeup and finding clothes that fit.  I guess what I am saying is that I get it, I understand when someone wants to look cute. We all want to feel beautiful and if this helps, who am I to judge?

I also want to be very clear 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.

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 massive 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.

I think sometimes our self-esteem is so tied up in how we feel about how we look that when ur reflection doesn’t match our expectations we are devastated..  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…crushing, to be honest. The first time I wore makeup and a wig I was amazed at how I looked but also destroyed that I didn’t look like a supermodel.  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 embraced who I was and became happier with who I am.  Acceptance can lead to confidence, which leads to happiness.

So, with that out of the way, let’s get started.


9 thoughts on “In-Between: A Beginner’s Guide to Crossdressing

  1. disagree with the blanket statement that passing is impossible. depending on the person it can be possible the majority of the time (speaking from personal experience)


  2. Maybe rather than saying “passing is impossible” add that you are really the only person you need to be passable to. It’s nice to be accepted in society for who you are but you have to accept yourself first. I prefer “accepted” to “passable” because no matter how good I look i’m sure at least someone out there sees me as “a dude in a dress”. But if I can go to the mall or downtown and I’m not accosted or refused service … If I don’t have everyone around me gawking and pointing and throwing vegetables at me … I’m accepted … and that feels good.


  3. Hey Hannah, I’ve found a woman that can’t wait to help me find myself as a woman. But we’re having issues with purchasing clothing on line such as tops and more importantly breasts/form and bras. Do you recommend any place locally (Twin Cities wise) for these items?



    1. I love shopping for lingerie at Allure. Read about one my visits here:

      When it comes to forms, I am afraid I don’t have a local place, I get my padding and forms at The Breast Form Store. Read my review of one of their products here:

      As for clothes, just keep trying different places. I shop everywhere from Target to Amazon to thrift shops.

      I hope this helps!

      Love, Hannah


    1. Not really? It is very hard to get a book published and if it does get published, it will be a very niche book, so I think it’ll be under the radar unless you are looking for transgender specific books.

      Love, Hannah


  4. Thank you for your post. At 48 I’m just now wanting to “fully” dress. I started with just pantyhose at a very young age which became more of a fetish. I guess still is, I just think they are extremely sexy. I don’t know why but all of a sudden I decided I want to one day venture out in public, just for a very quick moment at first. Like maybe pump gas and go, or pull over in a parking lot, get out and act like I’m checking my tail lights. I have taken a ride in a skirt and hose which I very much enjoyed. It really is a scary and somewhat confusing time and to be honest I hope that it’s not just a fetish thing. I know I’m going to need time to figure out where I am and how far I want to go. I did venture out to buy a pair of pumps from target which was scary and exhilarating. So thank you again for your post, no one particular person has the right way I know but hopefully with some more reading of others experiences and hoping as well to find kind supportive people to get opinions from, maybe I can figure this out. 😊


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