When I first began transitioning, it felt like there was an unbridgeable gap between me and the trans people I saw happily living out in the world. The idea of taking that leap of faith, of presenting openly as a woman, was absolutely paralyzing. Like many other trans people I turned to the fantasy of the boyfail, or the idea that I could boymode—publicly present as a boy—until it magically stops working. It's a ridiculous idea (for a number of reasons we'll get into shortly), but how do you become ready?
The most common answer I've seen is simple: Do it scared. And while this absolutely works for some people (and to some extent is mandatory), what happens when you can't? I transitioned at a very gradual pace, one far slower than average. I overprepared for every major transition milestone, but in doing so found the confidence to openly be myself that I'd never been able to at the start of my transition. And while it took me quite a long time to reach that point, the purpose of this piece is to outline my strategy for transition so that someone else in a similar position might have a better go at it. Because as much as boymoding can be a trap, it can also be a tool.
The plan is split into three phases. The first is to Feminize Your Boymode. Not only does this help make boymoding significantly more bearable over a longer term (and shockingly, just as if not more effective), but dipping your toes into femininity while in boymode can make it easier to take that full leap. The second is to Develop Your Girlmode. Working on developing gendered skills in private allows you to build confidence in your identity before taking things public. And the final step is to Do It Scared (But Prepared). It’s still going to be terrifying, but there are a number of strategies to help make the leap feel more manageable.
I want to be clear that transition is different for everyone and the things that worked for me might not work for you. This is all a very high level overview, and these are simply my own experiences—both the things that worked and those that didn't—and they likely won't map onto your life perfectly. But if you've been struggling to move forward with your transition, particularly with presenting openly as a woman, then some of this might be useful.
The key to a successful boymode is femininity. And while that may seem counterintuitive, I promise I can explain.
Before we talk about boymoding, we have to talk about passing. Passing is achieved when two conditions are met: Firstly, a person is perceived as their desired gender. Secondly, That person is not perceived as trans. These are both incredibly subjective judgements. Gendering is a largely subconscious process, one that’s deeply ingrained in our social systems and prone to the biases they hold, particularly those that treat cis men as the default.
Boymoding is about passing in reverse: To successfully boymode, you need to present as the wrong gender without arousing suspicion. Trying to put on a standard masculine front is setting yourself up for failure, because your discomfort is going to seep through. The average cis person is terrible at identifying trans people; their insecurities around this are one of the leading causes of transphobia. But instead, if you lean into your femininity, your comfort in your identity gives them far less reason to question it. They might think you’re a little weird, but you’d be shocked at just how much you can get away with before people start to really question things.
Around two years into my transition, I had a semester long group project in college. I didn’t feel comfortable coming out directly, both because I wasn’t confident in my ability to present femininely and because one member of the group project had made a couple of vaguely transphobic comments. Over the course of the semester, my group project partners had switched to calling me May, using she/her pronouns, seen me take estrogen, heard me try out my girl voice, and even pushed me to wear a dress to our final presentation, all while fully convinced I was a guy being roped into a bit.
There were three reasons I got away with this: Firstly, My baseline was already quite feminine. I showed up to class wearing women’s tees and jeans, and hormones had already started to soften my features. Secondly, the shift happened gradually, over the course of a few months. There were a few weeks before things got super explicit, and the steady drip feed made it harder to question. And lastly, I gave plausible alternative explanations for everything that was happening, ones that externalized my transness onto other people. Why was I taking estrogen? I lost a bet. Why was I using she/her pronouns? A friend bumped into us and just so happened to think it would be a funny bit. Why was I going by May? If I already had the pronouns then I needed a name.
Boymoding femininely comes with a number of benefits. It makes boymoding more sustainable over a longer term. It’s less exhausting to put on a mask closer to who you are, and it’s less work to cover up your changing body. But most importantly, it allows you to explore and develop your femininity on your own terms.
I want to be very clear that passing is not everything. While there are legitimate safety concerns to being read as trans, the vast majority of people simply will not make a big deal about it. But just as with attempting to present masculinely, if you attempt to present femininely without first building up the self-confidence to do so, that discomfort seeps through. The purpose of boymoding here isn’t to pass, but to allow you to explore and develop your femininity without the added pressures of being read as a woman so that you can feel more comfortable and confident in yourself when you choose to do so.
If you boymode until you pass, you’ll never stop boymoding. Your insecurities around being seen as trans will be read as insecurities around your femininity, and will only reinforce other people’s perception of you as a boy. There’s no moment, no amount of hormones or surgeries that will automatically switch other people’s perception of you from guy to girl. I’m being very blunt about this because these are feelings that kept me trapped in boymode for years, even if the ultimate results worked out for me. But transition is ultimately a very personal experience, and all of us come into it with our own baggage. If boymoding makes it easier for you to work on yourself, then it’s a perfectly reasonable approach to take, so long as you ensure that you actually are working on yourself.
But where do you even start? Transition is pretty all encompassing, but these are some pretty good areas to work on. Some of them can be felt instantly, others will take more time and work for the effects to really show. But all of them will help set you up with a strong foundation for transition, whether you do so the standard way or while boymoding.
Before anything else, make sure that your hormones are on the right track. Whether you’re already on hormones yet or not, I’d highly recommend reading through Katie Tightpussy’s excellent Practical Guide to Feminizing HRT in order to ensure that your hormone levels are effective. It took me years to get onto an effective hormone regimen, and you can save yourself so much anguish by doing this early.
Hormones can take a long time for the changes to show and those changes are often subtle. If you think your appearance hasn’t changed much, I’d highly recommend attempting to recreate a pre-transition photo. Try and replicate the same background, the same lighting, the same framing, only with your current clothes and body; the similarities help to draw out the changes.
No matter how good your hormone regimen is, if you don’t give your body enough energy, your body can’t do anything with it. As an added bonus, any fat you gain will go to the right places, which does wonders for shaping your body.
One of the easiest steps you can take is to swap out your existing wardrobe with similarly-styled women’s clothes. Not only do they make boymoding less mentally taxing, but women’s cut clothes will fit your body way better, and consequentially can make your feminization less noticable. There’s quite a bit of overlap between men’s and women’s fashion for you to play around in before going for anything explicitly feminine, and you’ll be shocked with just how much you can get away with in boymode.
Shopping in person can be terrifying, especially early on, but you can always shop online if you feel the need to. Otherwise, I’d highly recommend checking out local thrift stores for cheaper items, as well as going shopping with a friend to help make the process less intimidating.
When shopping, look for neutral basics that you can mix and match together. Not only is this incredibly cost effective, but having a strong foundation to build off of can make it easier to branch out as you develop your fashion. Many of the basics I picked up early in my transition—some jeans, sweaters, tees—are still part of my wardrobe today, where they sit alongside more explicitly feminine pieces that can really sell a look.
Whether you’re happy with your current length or trying to grow your hair out, get a haircut. Trimming off split ends makes it easier to grow your hair out, and the right haircut does wonders for framing your face. Asking for a feminine haircut can be daunting, especially if you’ve had bad experiences with haircuts in the past, but if you’re intimidated I’d recommend asking other trans people in your area for recommendations.
Try to find reference photos with similar hair to yours. If you have curly hair (like I do), find a hairdresser who knows how to work with it. Curly salons tend to be on the pricier side, but you’ll likely be able to get away with less frequent cuts, so it tends to balance out. Learn to take care of your hair; when you get a haircut ask your hairdresser for recommendations.
Estrogen will already do wonders for your skin, but there are some super simple ways to take things a step forward. If you’re starting out with skincare, I’d recommend the following basic daily routine:
I’m personally a fan of Round Lab’s Dokdo Cleanser and Moisturizer, and highly recommend the Biore UV Aqua Rich Watery Essence sunscreen (specifically the imported Japanese version, the American version is significantly less effective due to regulations)
In addition to the above routine, if you’re shaving regularly then do yourself a favor and invest in a decent quality razor (personally I’d recommend a safety razor, and to stay clear of electric/cartridge razors, but what works best for you is going to be incredibly dependent on your skin and hair) and use some kind of aftershave to take care of your skin. I’ve found great results with a 10% Azelaic Acid Suspension.
You’ll want to get started on hair removal sooner rather than later, especially if you pursue electrolysis. It’s easier to grow out your facial hair early in transition than when you’re openly presenting as a woman, and hair removal can take quite a long period of time.
For laser to work effectively, you need clear contrast between your skin and your hair. This means that if you don’t have light skin and dark hair, you’ll likely be out of luck. Laser hair removal isn’t permanent, but it will greatly reduce hair growth and can be an incredibly effective way to reduce shadow. It also tends to be cheaper and quicker than electrolysis, and is worth looking into if you have the right skin/hair combo.
Electrolysis is slow, painful, and requires you to grow out the hair first, but it’s also permanent.
Regardless of which method you choose, staying on top of your skincare is highly essential, especially in the days following an appointment. Your skin is incredibly vulnerable, so invest in some high quality sunscreen and don’t forget to re-apply every few hours.
Voice Training can be incredibly difficult and frustrating, but the earlier you start, the better. Your voice is one of the strongest factors in how most people gender you, and developing a natural sounding, feminine voice was one of the most important keys that allowed me to feel comfortable presenting as a woman. You’re going to sound weird at first, and voice training can be incredibly embarrassing—it’s inherently self-conscious. But it’s a lot easier to push through those awkward stages early.
I’m no expert in proper voice training technique (I mostly figured things out through trial and error), but the key to a feminine voice is resonance. Essentially, you want to move your voice from your chest to your head. If you can afford to, I’d highly recommend looking into professional voice training, but the first step is to play around with your voice whenever you get the chance. But find opportunities when you can—I used to talk to myself in the car on my way to and from work.
Getting a natural sounding voice requires consistency—which means dropping your old voice, even while boymoding. You don’t have to go full femme—how your voice is gendered is just as much about how expressive your voice is as it is resonance, and I’ve never had any issues speaking in head voice while in boymode, even early on when it sounded forced.
Voice training can be difficult and time consuming, but the best and worst thing about it is that it’s a skill, one that you can develop with practice. And starting to work on your voice early can help you get ahead of the curve, making your eventual transition into presenting as a woman far easier.
Good posture can completely change how people read your body. Unlearning bad habits can be difficult; Especially for sitting posture, I’d highly recommend setting a regular reminder on your phone or computer to check your posture every 30 minutes or so. Over time, it’ll get easier to maintain.
While it’s tempting to slouch if you’re insecure about your height, doing so only draws more attention to it. Slouching doesn’t actually make you look shorter; it broadens your shoulders and widens your silhouette, making you look more masculine.
Similar to posture, changing your walk requires a lot of intentionality. As hormones change your body, particularly if you’re young enough to see hip rotation, you’ll see your gait naturally shift into something more feminine. But you can help speed things up by paying attention to how you walk. Reducing arm movement can help shift momentum from your shoulders to your hips (but make sure they don’t look too stiff), and early on I found it helpful to visualize a straight line in front of me to walk on in order to narrow my stance.
Go out for a walk through a quiet park or neighborhood and pay attention to how you’re walking. Early on I found it helpful to record myself walking down a hallway to make sure things looked relatively natural; you’ll want to walk back and forth a few times so you can get past the stiltedness of recording yourself.
Unlearning muscle memory takes time; it’s going to feel forced and mechanical at first, but just like voice training consistency helps the results feel natural.
Most women have their entire childhoods to develop gendered skills, and attempting to speedrun the process can be incredibly intimidating—especially if you’re trying to do it alone. Before anything else, I want to make it clear that there’s nothing wrong with asking for help. Not only has every other woman been where you’ve been before, but asking other women for feedback on an outfit or makeup look is one of the most stereotypically feminine things to do; needing help doesn’t make you a failure.
It’s also important to note that womanhood is incredibly individual. What works for you won’t work for others. If a friend tells you she doesn’t like a top, consider whether it’s just not working or if it’s just not her style. And while most of the advice in this section is geared towards my own tastes and goals, if they don’t line up with yours that’s perfectly okay.
We need to talk about male socialization. Trans women aren’t male socialized, because gendered socialization is done to us rather than done by us. Male socialization is an oppressive force, one that attempts to shape perceived boys into men—and punish anyone who can’t fit into that mold. The consequences of this can be severe—most trans women have horror stories even before transition due to our discomfort with masculinity.
One of the consequences of this is the subconscious defense mechanisms we build to protect ourselves. One of the most important things you can do for yourself is to challenge those preconceived notions about yourself. What parts of your personality are innate, and what parts are constructed? Do you actually hate Taylor Swift, or were you just afraid to like her? How much of your irony is a defense mechanism? Working through these beliefs doesn’t inherently make you more of a woman, but it does bring you closer to yourself. Because you can’t figure out what kind of woman you want to be without first divorcing yourself from the boy society expected you to be.
It can be easy to feel like getting into stereotypically feminine interests post-transition is performative, but doing so can be just as authentic as anything else you enjoy. Most importantly, these interests often come with overtly feminine communities. While that can feel incredibly intimidating early transition, knowing that you have a shared interest with other women can make it easier to work through your imposter syndrome. Some of the most profound experiences I had early in my transition were at pop concerts and romance novel book launches. Having a shared interest made it easier to feel like I belonged, and allowed me to truly feel like a woman in a way I hadn’t before.
The wardrobe you’ve built up in boymode provides an incredibly strong foundation of basics to work off of. But branching out into more explicitly feminine and statement pieces is completely transformative. Building confidence in your fashion makes it easier to build confidence in yourself, and an outfit that works with your body while explicitly signalling femininity will completely shift how others perceive you.
Alt looks tend to draw more attention, but that attention is focused on the look, not you. Personally, I’ve found that mainstream fashion can be easier to build confidence with; while it can draw more attention to features you’re insecure about, the right techniques allow you to balance your frame, and being able to blend in can reduce the pressure of openly presenting femininely. Ultimately, aesthetic preferences are incredibly personal. The advice in this section is largely aimed at more mainstream looks, but many of the same skills will apply regardless of aesthetic preferences.
One of the easiest things you can do is to copy off the people around you. Fashion is heavily dependent on your environment, and the easiest way to pickup what works for your area is to copy the people who live in it. An outfit might be completely normal in New York City, but stand out in Idaho.
Take note of the fact that you had to force yourself to pay attention; most people aren’t going to pay nearly as much attention to you.
Try to find people with similar bodies to yours; what works for them is more likely to work for you. If you see something you like, take note of it for the next time you go clothes shopping. But most importantly, pay attention to the details. You’ll start to pick up on what colors and shapes work together and how to accessorize an outfit.
While shopping in person can feel incredibly terrifying, I’d highly encourage you to do so. Not only does trying clothes on in person help you ensure a good fit, but it allows you to take chances on clothes you wouldn’t have otherwise considered. Going shopping with a friend can help provide a buffer for your anxieties, as can shopping at busier stores where it’s easier to fall into the crowd.
Feeling insecure might be the most universal part of womanhood, and can make it terrifying to ask for feedback on a look. Whether you’re out shopping with friends or sending pics to your group chat, having an outside perspective can help give you confidence in a look and catch things you overlooked.
It’s important to keep in mind that someone else not liking an outfit isn’t an objective metric or a personal failing. Everyone has different tastes, and while external feedback can be valuable you should always go for an outfit that you feel good in. Putting together interesting outfits requires taking chances, and those chances won’t always play out. But even when they don’t play out, figuring out what doesn’t work is just as important to developing confidence in your fashion as figuring out what does.
Every body is different, and learning the shape of your body is key to both highlighting your best features while also drawing focus away from your insecurities. One of the easiest tricks is to pair high-waisted, wide-legged bottoms with small, form-fitting tops, which can do wonders to bring out your hips and balance out your shoulders.
Not only do accessories help to elevate a look, but they can also help gender it too. Pairing a t-shirt and jeans with a cute belt and matching bag can push you from an androgynous outfit to an explicitly feminine one. Look for versatile items that fit well together.
Different skin tones work with different kinds of jewelry. Gold jewelry works best on warm skin tones, and silver jewelry works best on cool skin tones. If you aren’t sure what your skin tone is, go outside and look at the veins on your wrist: If they’re closer to green, you’re cool toned; if they’re closer to blue, you’re warm toned.
Coordinating the right accessories can make an outfit look more deliberate, and can push even the most androgynous looks into firmly feminine territory. Plus, bags are so much better than pockets anyway.
Makeup can be incredibly daunting, but just like voice training it’s a skill that you can learn. A little bit of makeup can go a long way in terms of pushing an otherwise androgynous look into reading explicitly feminine. In general, I’d recommend going for a lighter look until you know what you’re doing. While it’s incredibly tempting to cover up as many features as you can and makeup can completely transform the look of your face, any mistakes you make become significantly more visible, and can make going out significantly more stressful if you aren’t comfortable enough to clean up your look in public. Still, I’d highly recommend practicing heavier makeup in a comfortable environment so that you can pull it out when the occasion calls for it.
This is far from an in-depth tutorial, and you’ll likely want to continue working on your makeup skills outside of the below suggestions. But I’ve found the following routine to be both easy to learn and incredibly low maintenance.
For day to day looks, I’d recommend using tinted moisturizer over foundation. It’s a lot easier than foundation, as well as harder to screw up.
Matching foundation to your skin can be incredibly difficult without shopping in person. I’d highly recommend shopping in person and asking for help, but failing that you’re going to need some trial and error. I’d recommend picking up some cheaper samples in order to narrow down what shades match your skin, and then matching those shades with higher-quality products. But seriously, shop in person and save yourself a ton of headaches.
I strongly recommend doing any eye makeup first. Your eyes tend to require more precision, and doing them first allows you to easily clean up any mess that gets made. Mascara can do a lot to bring out your eyes.
I’ve found that the easiest way to apply mascara is to do so while looking down, which helps create some extra space between your eyelashes and eyelids.
Day to day, I’ve found that a nude lip gloss can do a lot to elevate a look while being pretty difficult to screw up. Matte lips are incredibly visible when they start to fade or smudge, but gloss is far more forgiving.
Once again, it’s incredibly important to emphasize that boymoding is not a thing you are, but a thing you do. It’s not a binary—you don’t have to go from presenting as a boy to a girl in all contexts, you can pick and choose and work your way up. So how do you know when you’re ready? The bad news is that you probably won’t. But doing it scared is very different from doing it blind. The skills you’ve been developing will make it easier to navigate your womanhood, and in my experience there are a couple of other factors that you can control in order to help make those initial transitions from private to public womanhood feel more manageable.
Going out with friends takes away some of the pressure, especially your first few times or in a new environment. Having friends on hand can be an invaluable distraction from your insecurities, and can make it significantly easier to give yourself permission to just be a woman. After all, they want you to be yourself too.
The busier the environment, the less attention anyone is paying to you in particular. Cities are a great place to explore your femininity, and busier stores are often less intimidating to shop in. When you’re just one person among dozens or hundreds, absolutely no one is paying attention to you.
I found events to be incredibly helpful for presenting as a woman. Not only do they give something to draw focus away from you, but dressing up for an event can often be easier than putting together a casual look. Concerts are great for this. There’s often a broad theme to work off, and once the artist is on stage absolutely no one is paying attention to you or your look. Plus, having an event you’re genuinely excited about helps balance out the fear.
Early on, one of the most helpful techniques I found was to distract myself with discomforts not directly related to being read as trans. If you’re worried about whether or not your top is showing too much skin, you aren’t thinking about whether or not you pass. Use this one sparingly, but it can be helpful for that initial push.
When you go out and everything goes well, ride that feeling and do as much as you can. The more time you spend presenting as a woman the easier it becomes. Go get some food after a concert or wear that outfit you just bought out. The more exposure you have, the better.
If you’re still feeling scared, something you can do is to attempt a few practice runs before actually going out. Pick a place or event—real or hypothetical—coordinate a look, and mentally run through it in order to identify what your biggest fears are and what you could do to help reduce them. And if you feel good enough, why not go for it?
I can’t emphasize enough just how valuable friends can be for giving you the final push. From reassuring you through your insecurities to helping distract you from your fears in the moment, having someone else to encourage you can help bring out your confidence.
Ultimately, the only person who can choose to take the next step is you. But that doesn’t mean you have to do it alone, or that you have to do it blind. When you have successes, document them so you can look back to them when you’re scared. If you hvae failures, document them too, so you can identify where things went wrong and what you can do differently. It’s always going to be terrifying, especially the first time, but it really does get easier. And if you’ve been following this guide, then you’re more than prepared.
There is no end to transition, and even if there was one, this guide stops short well before it. But once you become comfortable presenting as a woman in public you open up so many opportunities for yourself, from coming out at work and legally changing your name to feeling comfortable going to the bathroom in public and meeting new people.
Getting to this point took me almost five years. Much of that time was wasted, feeling overwhelmed with contradictory information and too afraid to ask for help. If there’s anything you take away from this piece, it’s to let the people around you help you. As individualized as transition is, you don’t have to do it alone.
So what now? Well, that’s up to you. You have the tools you need to shape your own womanhood, and only you can determine what that looks like.