Learning about dressing to transition can be utterly overwhelming. And just because you find something cute doesn’t mean it’s something you should wear.

We’ve talked a bit about body types before- but consider this the master post.

Let’s be clear, you can wear whatever you want. But if you are looking to present a “feminine” figure, then you have to be aware of certain rules. If you don’t care to camouflage, or are more androgynous or genderqueer- then by all means get down with your bad self. This is just meant to be a guide for minimizing masculine features.

Body Types

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First you need to know the types of bodies we are dealing with. There is the hourglass, pear, apple, inverted triangle, and column. Each have certain properties that will have to be addressed.

Hourglass

Right off the bat, let’s be honest. Sadly, not many trans women are blessed with hourglass figures. If you are, then you are a lucky one indeed. Your battle is a downhill one. After all, this is usually the most desired shape. It means your shoulders and hips are roughly the same width and your waist is smaller and more defined. It’s the stereotypical female shape. Think Marilyn Monroe.

Pear

It’s just like it sounds. Your shoulders and chest are smaller than your waist, hips, and thighs. In order to draw attention- you will be looking to pull the eye up north, away from the mid-section.

Apple

Apple bodies have a larger waist and an average chest, usually with a wider back, flatter butt, and smaller arms and legs. Again, you’ll want to divert attention from the middle of your body towards the legs, bust, and arms. Very common shape for transgender women.

Inverted Triangle

This is another really common shape to see on transgender women, and a frustrating one for many. Broad shoulders and slimmer hips and mid-section. As you can imagine, you will want to draw the eye away from the bust and shoulders. We will talk about that below.

Column

This is a slender shape with narrow shoulders, chest, and hips. Almost no body shape or curves to be seen. But that can be fixed by defining some shape in the body.

The Clothes

Here are some tips for different types of clothes. Remember, this is just a guideline.

Skirts and Dresses

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Fit and flare, or A-Line dresses and skirts are wonderful for creating a wider shape for the hips and drawing the eye. The contrast of fits can really minimize the chest and shoulders for those apple and inverted triangle types. However pears should avoid these in general, as it exaggerates the shape. Columns can pull this off too, but make sure to go with a more moderate flare or you might look more like a bell than a belle.

Avoid body contouring, or bodycon, style dresses or skirts for the most part. You will create no shape, and only accentuate your natural shape. And, what most people won’t tell you- you will easily be able to see if you are wearing any kind of shapewear. Any hip pads, or butt pads, or spanks are going to be painfully obvious.

Pants

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I know skinny jeans and pants are in. But this is another tough one for trans women to pull off. Not only do you run into our natural problem between the legs, you are again not creating a new shape. Just showing what you already have. Boot cut is your friend. An added bonus of boot cut pants? They can help hide larger shoes for those girls that have slightly bigger feet. Skinny jeans will REALLY exaggerate the size of your feet. Not good for most of us.

Tops

The biggest rule I’ve learned is this- just say no to cap sleeves. Yes, they look cute, but they will absolutely not hide your shoulders at all. They exaggerate them to the nth degree. You might as well put on a shoulder-padded blouse straight out of “Dynasty”.

Go for structure and flow, avoid form-fitting. Again, we land on this point. A little clingy is fine, but you want a little structure to it. Skintight is not going to flatter you unless you naturally have a very feminine shape. And luckily, flow is in right now. This summer all I am seeing practically are flow-y tops. Usually sleeveless. And believe me, sleeveless is far better than cap sleeves. And no- I have no clue why.

And go for v-necks over deep scoop necks. A scoop neck creates a wide picture. A v-neck draws the eyes down towards the chest and mid-section away from the shoulders. And believe it or not- a v-neck can help slenderize the face as it draws the eye down.

Belts

So, belts are a double edged sword. They can be wonderful tools for creating shape by defining a waist, but with the wrong body shape and wrong best- they can be horrid. Belts are great for pear, and inverted triangle, and especially column body shapes. A solid-color wide belt can really cut into (visually) a mid-section and carve out (visually) a waist to create a curvier look. On an apple, a wide belt is going to look…not good. My advice is that you still need to create a line there to define a waist- so just go with a thinner belt. They look better on wider mid-sections.

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Shoes

I don’t want to be the one to break this to you- but shoes are often the bane of a trans woman’s existence. Either you can’t find shoes in your size, or you find a display pair that looks cute but does NOT translate to larger sizes well, or everything in your size looks like it was made on a dare. Finding shoes that look good, feel good, and cost…good are little marvelous unicorns. But there are things you should know.

In general, your size in women’s shoes is two sizes larger than the size of your old shoes. There is variance- but that’s pretty typical. Please, don’t wear smaller shoes because they are cuter or you are self-conscious. All you will do is mess up your feet and be miserable. Believe me- it’s not worth it. I’ve done it.

Next, boots are tricky as well. I find it odd that I’ve always been able to wear boots in almost one size smaller than any other type of shoes. So strange. However the problem is that I have larger more muscular calves. So if you don’t have average to slender legs, you might have problems. I have tried on and ordered many a boot where apparently my calf can’t be taymed and will not fit.

Toes. Okay, this one is a tough sell but hear me out. Pointy toes are not your friends. This is the secret women have learned over the years. Yes, pointed toes can look very elegant and feminine. But in order to accommodate your toes and still point- the shoes become much longer. This is going to make your feet look MUCH larger. And it’s really tough to find a pair that are comfortable. That’s pretty important for those who are just getting used to women’s shoes.

Finally- a bummer for summer and one that many trans women don’t want to accept. Sandals, they are just a difficult thing to pull off. Larger feet just become exaggerated in sandals. With more skin available and toes showing- there is less hiding your feet. So if you are trying to camouflage, this is not a good idea. Unfortunately, most of us hold remnants of our old life in our feet. They are usually larger, and not as well taken care of. So keep that in mind.

General Rules for Dressing to Transition

Dark Colors De-emphasize and Light Colors Emphasize. Use accordingly

That means, if you have large shoulders and chest, white or neon green is probably not your frand.

Stripes and Patterns Can Be Strategic

  • Busy patterns on a top can really help a pear shape. Conversely, a busy pattern on a bottom or skirt can help an inverted triangle
  • Vertical stripes lengthen and horizontal widen. Use this knowledge accordingly. And a note, wide stripes work best on fuller figures. But diagonal stripes work best.
  • Blocks of color are great for defining shape for apples and columns. Strategically placed side blocks with subtle shaping towards the middle can help create more of a figure.

dressing to transition

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Wear Clothes That Fit

Should be a no-brainer, but I see it often. And I have been guilty too. When you are trying to build a closet you grab whatever you can. And often when first shopping in public you might be too scared to try something on. Or you get it online and it just doesn’t fit. Don’t wear it. Sell it, return it, or donate it. It will do you no favors. Remember, tight clothes emphasize a male figure and loose clothes just look sloppy and define nothing at all. And if you are bigger, buy your right size. You will not look magically smaller if you can squeeze into an XL if you need an XXL. Suck it up, and buy the right size. There is no shame in it. Women come in all sizes.

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Dress Appropriate to Your Age

Again, not dictating what’s okay to wear. But it’s just a simple truth that dressing for an age that doesn’t suit you is a sure way to stand out. For us that means getting clocked. That means if you are fifty, body contouring minis and leggings that say “Juicy” are not your best bet. There are plenty of ways to dress fashionably and keep a youthful look without going to cliches. Believe me, it will boost your confidence. Dressing like you are an 18-year-old “scene kid” will not boost your confidence.

Keep it Current

This is another “unwanted attention” reminded. Wearing leopard print spandex and leg warmers is not the norm, and hasn’t for a long time. Some people can pull off retro looks, but if you can’t- you should avoid it. If for no other reason, avoid so you don’t hurt your confidence. Ask yourself how many cis women you see dress that way. That’s a good guideline to go by.

As a result I see, usually older, trans women often sticking to the era they wish they could have dressed or when they first felt feminine. That leads to a lot of middle-aged trans women dressing like extras from “Dynasty”. You are going to stick out. The silk blouses, gaudy dresses, and ungodly shoulder pads are not a good luck and will get you stares. A cis woman would get stares in those get-ups, so this isn’t a “picking on you” thing. Believe me, I wish I could pull off retro and pinup, but it just doesn’t look good on me. I’m not one of those people.

Don’t Wear Uncomfortable Clothes

This goes back to the size thing, but also any cuts that make you uncomfortable or just things that don’t look right. Don’t wear something just because it’s in the closet. If you are uncomfortable, it will show. You will look uncomfortable, and your confidence will plummet. Plus, you’ll just be plain miserable. You may have always dreamed of wearing skyscraper heels. But if you aren’t used to them you will be in pain as well as walking like a baby gazelle.

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Preemptive Action

I have no doubt this will get shared or commented with great exasperation from those who take offense at everything with remarks like, “HOW DARE SHE TELL ME WHAT TO WEAR!!!” or “WHO DOES SHE THINK SHE IS!” or “I’LL WEAR WHAT I WANT!!!!!!!11111OMGWTFBBQ”.

The fact is, these are just general fashion and clothing tips. And they apply to everyone, cis/trans/male/female/whatever. This information is gathered from years of experience, suggestions, and research. And I think if you give them a chance, you will find clothing less intimidating and have greater success creating the look you are going for.

In the end, wear whatever you want that makes you feel good. These are just guidelines and suggestions that will help those that want to pass and not get unwanted attention. If you don’t care, then great- you do you. Frankly, I could care less if you want to go to the Piggly Wiggly in a Supergirl costume, moon boots, and a top hat. Just don’t get upset if you get stares and weird looks and start screaming about “Why is everyone looking at me!!!”.

No need to get in a tizzy- it seems like this article just wasn’t for you. They won’t all be.

  • *Great* article – I learned some new things!!

  • Jani Louvel

    NOBODY wears bootcuts anymore, and you’re telling folks to be current?

    lol k