What to Wear

In my most recent post I wrote about determining your body shape as well as how to find your measurements.  Measurements are so, so important because the world of dresses, skirts, heels, and everything else is so different compared to boy clothes.  A medium dress shirt never translates to a medium blouse.  There are some rules of thumb, such as your stiletto size being a size and a half bigger than your boy shoes, but even that isn't always reliable.  When shopping for an outfit, check the measurements of it as opposed to the size itself.  In some stores I am a size 10, but in others I am a size 18.  

To recap:

  • If you are curvy and do not have a defined waist, then you have an apple shape.  

  • A pear-shaped body has hips that are broader than their shoulders.

  • Many cisgender men have a rectangle-shaped body, meaning straight body lines with shoulders, bust and hips that are roughly the same width and little waist definition.

  • In boy mode, my body is more of an inverted triangle, meaning my shoulders are broader than my hips.

  • An hourglass figure is when your shoulders and hips are balanced and you have a defined waist.

The first book I ever read about crossdressing was 'The Lazy Crossdresser' by Charlie Jane Anders.  They wrote that wearing women's clothes is not necessarily the same as looking good in women's clothes.  That always stuck with me.  Yes, the dress FITS but is it right for my body?  Does it minimize what I want it to (such as my shoulders) or does it draw attention to what I feel is one of my best physical characteristics (my legs)?  Most clothes are designed to look a certain way when you wear them.  A pencil skirt is designed to hug your body and show off your curves.  If you have a rectangle shaped body, then the potential of a pencil skirt is almost wasted.  You'd be better off with an A-line skirt or a flared or pleated skirt.  BUT, if you change your body shape- by wearing thigh and hip pads- then a pencil skirt will look amazing on you.

Your body can change over time, through diet and exercise, for example.  I used to be a size 18 and am now down to a size 12.  Certain dresses no longer fit, and even if they did, they would look a little off since my body shape is so drastically different.  When I first started to move from simply underdressing to going completely en femme, my body looked different.  At first I was just wearing what fit.  But over time I added padding and forms and what a difference this makes.  Not only with my body shape, but how clothes look and fit.  I can try on a dress and it looks... well, it might look okay.  But when I try it on with pads and forms it looks completely different.  Bodycon dresses are a perfect example of this.  They look boring if they hug my boy body, but once I have my thigh and hip pads... wow.  It's a completely different dress.

So the question is, what do you wear now that you know your body shape?  

The easy answer is wear whatever you want.  I mean, that's the whole point of accepting and embracing this side of us, isn't it?  But most clothes are designed with a certain body shape in mind.  Make sense?  Okay, let's go shopping.

First of all, think about what your goals are.  There may be a certain style that is designed for your specific body shape, but many clothes are designed to draw attention to, or detract attention from, parts of your body.  If you are trying to emphasize or downplay certain features, then seeking out clothes designed for your body shape should help with your goals.

If you have an apple shaped body, start looking for clothes that accentuate your shoulders, as well as your bust (forms help with this!) and your neckline.  Cold shoulder tops (tops with an open shoulder in the sleeve) can do the trick as well as tops and dresses that have thinner straps.  Plunging necklines will look divine on you.  Pair these tops with a pair of high-waisted black pants or if you are really feeling yourself, leatherette leggings.   Black can help elongate your legs and is always a nice balance with a colored top.  If you are looking for dresses (and who isn't)?, a wrap dress or an off-shoulder-dress will work beautifully.  Nothing draws the eye like skin.  

If you have a pear shaped body, wear clothes that draw attention to the top half your body.  Brightly colored clothes and cute prints can absolutely do this.  I think many of us are hesitant to wear colors that attract attention.  At first I wanted nothing more than anything to blend in, and a pink dress or a cute top didn't really do that.  Then I realized I am a six foot tall transgirl and I am not going to blend in anyway, so why not wear what I want?  Having a pear shaped body may also bring you out of your comfort zone in other ways as it is recommended to show off your shoulders too.  For the loooongest time I avoided this.  I didn't wear spaghetti straps because I thought my shoulders were too broad and masculine.  I don't think that anymore and I refuse to hold myself back from wearing what I want to wear.  As for matching that brightly colored top, pair it with a skirt that is not too tight... something that doesn't cling to your body like a pencil skirt will. 

Most men have rectangle shaped bodies.  A bright, eye-catching top and a flared skirt looks amazing on this body type.  I recommend a brightly colored top, something with a scoop neck paired with a short black skirt.  The bright color will downplay your shape and the skirt... well, it's fun to wear a short skirt. Not necessarily a tight skirt, such as a pencil skirt, but an A-line skirt or something that flares out.  Without using forms and/or padding, peplum designs will also help a girl with a rectangle shape create the illusion of a curvier figure. A peplum flare, either on a dress, skirt or top, will draw attention to your waist and make your hips look wider. Also recommended for those with rectangle shapes are skirts or dresses with volume-increasing details like ruffles, bows, or other embellishments. 

Girls who have an inverted triangle shaped body will look sexy in clothes that accentuate their hips and neck.  Tops that have a v-neck that show off collarbones, for example.  Since this body shape may have shoulders that are broader than their hips, you can wear skirts that are a little fullerFitted jackets with a nipped-in waist and flared bottom hem also look great on this body type, since they help balance out broader shoulders. 

Finally, the hourglass shape.  I do not have an hourglass shape naturally, but I can kind of cheat and get this shape with help from my thigh pads, hip pads and a nicely cinched corset and gaff.  It's a lot of work but it allows me to show off these new curves. When you have an hourglass figure, virtually everything looks good on you. Fitted tops and other form fitting clothes really help accentuate this shape. A pencil skirt will also hug your body and create a very alluring silhouette.

Of course, you can ignore these guidelines as much as you want.  Accepting and embracing your gender identity is not always easy.  Your gender identity journey can start with you noticing and longing to wear a beautiful dress.  Wearing what you want is a symbol of conquering yourself, in a way.  You may have denied this side of you for too long and finally, finally wearing that outfit is a testament to loving and embracing yourself.

Love, Hannah


  • Andi

    Thank you so much Hannah! I’m just starting my journey. I can not begin to tell you how helpful and inspiring you are! You make me feel brave!

  • Amyrakunejo

    Good advice for those of us looking to find our own style, but need a base to work with.

    Not so much for those looking to expand into a certain fashion style though, as certain aspects may make finding the fit a bit more difficult.

    That said, you're gorgeous in whatever dress or cute outfit you wear, Hannah.

    Love, hugs,

Leave a comment

Please note, comments must be approved before they are published