When you first realize you are trans it can be very easy to fall into your personal ideal of what ‘female beauty’ looks like, and you end up dressing in a way to mimic that aesthetic. However, it can come to bite you in the ass rather quickly with how other people perceive you. If you live in an area with people or go outside, other people are going to see you at some point and will assign a gender identity based on your appearance. It would be cool if it weren’t this way some days but that’s just a fact of life unfortunately. 

An important step in a transition is obviously feeling validated and comfortable in your body so if it gives you enough euphoria to wear what you want, go ahead! I encourage it greatly. Just know that eventually that effect does wear off so don’t specialize your whole wardrobe into whatever your beauty ideal is at the start of your transition, it will almost certainly change over time, particularly as you learn to dress for your body shape.

Dressing up in elegant dresses with high heels and stockings might feel great for validation of your identity but it’s very different from how you’re going to dress outside. People expect you to assimilate into society a bit and look the part so it’s important to understand the fundamentals and diversify your wardrobe rather than becoming the feminine beauty you picture yourself to be one day.

When I first started to buy women’s clothes my idealized feminine beauty was ‘suburban yoga mom’ which is very specific but fairly common. As a result, I purchased a lot of exercise clothes that I wore without much thought into matching them. Thankfully where I live it kind of worked as leggings are ubiquitous but now that I have developed my own sense of self more, I have all of these clothes I rarely wear.  I would often dress like the following, compared to 1 year later, and another year, and 1 more after that.

As you can see, my suburban yoga mom phase never lasted very long, although some aspects of it did persist in terms of core purchases like with my jackets. Part of the problem (at least in my case) was that my choice of aesthetic did not seem serious to the people I would ask for help. People who I would have considered my friends prior to socially transitioning were far less eager to hangout with me if I asked for help shopping. Obviously transphobia is pretty cringe but in my personal experience it stopped being super apparent (in the outside world) once I fit in with other women better.

While not everyone has the opportunity to medically transition, or even wants to, the first few years of transitioning are always going to be the hardest socially as you typically clearly signal that you’re transitioning but have not completed transitioning nor possess the finesse to have the “feminine aura” that most women will search for when looking at you. 

The easiest way to balance this is with more subtle ways of dressing. Jumping right into it with mini skirts and a full face of makeup will probably backfire unless you’ve had a lot of practice in the, sometimes literal, closet. It took me a full 2 years from realizing I was trans, and 1 year transitioning, to ever even try on my first skirt. This is what that outfit looked like in the store.

Obviously, not a great look! However because of the gender euphoria I felt wearing the skirt it blinded my better judgement and I wore this as you see it. There were plenty of other mistakes I made as well such as parting my hair WAY off to the side because that’s just how it grew in. I’m not necessarily saying you have to take things as slow as I did but also you should listen to the people around you, they’re usually not malicious!

Tweaking these things over time or getting ‘professional’ advice from people is something I can’t recommend enough. The next time you feel like changing your hair, ask a hairdresser what they might recommend, they typically know what will work for you and your face shape.

The same applies to clothing. If you feel comfortable enough asking people who work in the store for help, also ask them what they think looks best on you from what you picked. In my opinion a second voice is damn near mandatory for every purchase/decision to make sure you’re not deluding yourself into thinking something looks good or isn’t worth the money you’re spending. 

Let’s take this outfit for example, what would you change to make it more feminine? There are several “right” answers. Let’s start with a very androgynous look and progressively make it more subtly feminine.

We can change the color of the jacket to a softer color like this light blue

We can change the shoes to ankle boots

We can change the shirt’s neckline

Or perhaps adding a pattern instead

Even just doing a ‘french tuck’ for the shirt can make a difference to define where your waist is

We can change the cut of the jeans

We can add jewelry

And to go the extra mile, we can even add a scarf

This is just an example of all of these subtle queues that can accumulate in how you present yourself to people that signal ‘woman’. Not everything is mandatory but if you look well put together it really goes a long way. Just be careful not to overdo it as that can backfire. If you look super feminine but don’t match the part socially it may catch strangers off guard. 

The same can go for wearing colorful things! It might seem very easy to just wear bright colors because men’s clothing is nothing but earth tones and neutrals but you need to learn how to balance them out. Color theory is an important tool to use, which I have a brief post explaining, but in order to make sure you don’t make mistakes by looking like a Cyberpunk sign. Using it, that’s why this outfit has a ton of colors but still works.

If you start wearing items that don’t go well together at all it can really be off-putting visually. Colors have different tones to match so a Neon yellow won’t be the same as a solid yellow when it comes to pairing. If we use this top as an example, we notice how the neon yellow top goes better with the brighter blue jeans.

Tread carefully when it comes to having a very colorful wardrobe where you try and mix an match things all of the time because finding colors with the correct tones to match is very difficult. You don’t want to draw too much attention to yourself either while still figuring out the basics. Pair solid colors together with neutral or white and black items until you feel like you have mastered it, and then move on to more varied color palettes.

These pink jeans don’t go better with more pink, they need room to ‘breathe’ so it looks better with a white top.

---

Using your former clothing is also something I advise against in most cases. The cut is rarely going to be flattering. If you have basics that are white and black that really suit you just keep them around for layering or more androgynous looks. I have shirts that I still do that with because they’re comfortable and can add a nice touch but I would never wear them without a jacket because of how they make me appear bulky. 

Another related topic is buying items that don’t actually fit you. Shoes in my size are fairly rare to come by so I’ve often tried to convince myself that a pair of shoes fits me when I know they’re not quite right. I go into this in more detail on How to Build Out a Shoe Collection but the same premise applies to clothes. Go shopping knowing your measurements, especially if it’s online and follow the brand’s size guide. If you don’t know your size yet it can be hard to know what actually fits you, women’s sizing is a guessing game! I have clothes that are XS – L so truly there’s no telling anything. Here is a guide on finding your measurements!

I always recommend trying the item on in 2 sizes so you can get a feel for which suits you better, just know if you order 2 online and return 1 that it most likely won’t be restocked and instead heads to a landfill, yet another reason to shop in person if you can. And make sure you have a full range of motion by lifting your arms and touching your head if you think an item is too tight.

And finally, take it one step at a time. You don’t need to become a fashionista instantly, and probably won’t be for a long time. I got lucky in getting stylist training but I still slowly built up my wardrobe over 6 years, buying 1 or 2 nice things at a time. My biggest regret is buying 300$ worth of stuff for makeup when I had never even put on my own eyeliner.  Most people aren’t wearing glamorous makeup looks everyday because while they look really nice, they’re time consuming and harder to master. I personally never wear makeup aside from maybe a bit of concealer when I have a massive pimple because I simply touch my face too much. Try to avoid buying expensive clothes for occasions you never have such as a ball gown if you work in a warehouse for example, there’s probably little overlap in occasions where you need a ball gown.

There’s no pressure to be anyone but yourself so don’t try and force yourself to be an ideal of someone you aren’t. We all have pictures that we can look back on fondly but if your first instinct is to cringe then you’re on the right track because that’s called growth 🙂