Cross Dressing Clothes for Beginners

What is cross dressing? For the purposes of this blog, it is simply the practice of wearing clothes associated with another gender. This could be a man wearing a dress or skirt, a woman wearing a suit and tie.

Of course, it's quite a bit more complicated than that. Clothes don't have an inherent gender, and the transgender community shows us that personal gender is not always as it might seem on the surface. Nevertheless, using this simple definition allows this discussion - if I want to cross dress, masc to femme for example, how do I start?

There are many reasons people cross dress. All of them are valid. If you have the desire to wear women's clothing as a person who was assigned male at birth, whether you feel this makes you a woman or not, you have the right to. Cross dressing is self-exploration and self-love, and it can be tremendously empowering. En Femme exists to help you in this journey.

A crossdresser in a dress

There are many components to cross dressing, from makeup to shaving or reducing body hair and more. For the purposes of this blog, the topic is limited to clothes or articles of clothing. What do I look for? What size? Where can I shop?

How do you start cross dressing?

You might have a clear image of what your feminine look should be. Or you could be exploring, unsure of the style that will suit you. The only way to begin to know is to try. Follow your instincts. If you're fascinated by one dress, try it (or a similar one) on and see how you feel. It all starts with recognizing that untapped feminine side and embracing your personal style.

The essentials

First, let's cover the items specific to a crossdresser. Because of anatomical differences (the obvious and the subtle) between men and women, it's not always as simple as throwing on panties, skirts, and heels.

The amount of shaping, contouring, and tucking you choose will be highly personal. Some crossdressers want a highly "feminine" silhouette, with an hourglass shape and accentuated bust and rear. Others may not want to alter their natural shape - and that’s OK and just as valid.. But it's always important to know your options, and at En Femme, we offer one of the largest varieties of clothing options you can find anywhere., 

Body shaping

These are the items you can wear to change your body's silhouette, before donning the dresses and shoes that will define your look.

Body shapers

For tweaking the shape of your waist, hips, and derrière, there are  body shapers. There's a lot of variety here, and you may want to experiment with different levels of change. Choose a shaper that accentuates what you already have. Looking for just a slight change - choose shapers that smooth and highlight vs those that add padding or inches to your hips.

A hip shaping body shaper

Breast forms

For defining a bust shape or filling out your favorite dress,  breast forms can be a crucial part of a crossdresser's wardrobe. En Femme carries a wide variety, so if you want a subtle shape or something truly buxom, we've got you covered. Silicone breast forms in larger sizes can attract a lot of attention - think about size carefully depending on how you are looking to create your shape. For example, if you are tall without a lot of curves, smaller forms can be a simple way to create shape.  If you have curves and shape already in your hips for example, you can add larger forms for that classic hourglass silhouette.

Breast forms aren’t for everyone however so when thinking about your bust, ask yourself what you see as enhancing your form.  Breast forms can be simple silicone enhancers all the way to a full bust, a D cup or larger. 

Silicone breast forms for crossdressers


Corsets are famous (or infamous) for accentuating the natural curves of a woman and having a glamorous look all their own. Corsets are the ultimate in waist training and can be a great way to create definition in your body.  At En Femme, we specialize in the underbust corset - a corset that focuses on the waist and torso and ends just below the waist line. Take a look at our collection to see if their distinctive look calls to you.

A crossdresser wearing a corset from behind

Tucking Panties or Gaffs

Male clothes are designed to accommodate those features that garnered that gender assignation at birth: the genitalia. It can't be ignored, as feminine clothes simply aren't cut for the space that you may need down there.

Thankfully, for that purpose we have tucking panties or gaffs - a specialized panty that allows us to tuck everything out of the way, ensuring your dress keeps a flattering silhouette all the way down.

En Femme offers one of the largest varieties of gaffs. If you're not sure which is right for you, check out our "Finding the Right Tucking Gaff Panty" article for some advice.

Transgender women wearing tucking panties or gaffs

Clothing time

Grab a measuring tape, because it's time to buy some stunning clothes, and you'll need to know your measurements. If you were assigned female at birth, you've probably known your dress size for a while. But for those of us who might be buying a dress for the first time, it's not always obvious.

To find your measurements, there are three primary locations.

The first is your waist. Measure right on your belly button, and don't unnaturally suck your belly in. You need a dress to be comfortable, so relax when you're taking the measurement.

The second is the chest. Take this measurement 2-3 inches below the nipples, right under the pectoral muscle.

The third is the bust. Take this measurement at the nipples, first without any breast forms, then a second measurement with breast forms (if you plan on wearing them).

Armed with these three measurements, shopping for women’s clothing online or in-store will be much easier to navigate. Go to your local mall or women's boutique. It's your right to shop where you please, so go to those stores that catch your eye.

A crossdresser wearing a dress

Or, shop with us at En Femme!  We use a proprietary sizing guide using height, weight and body type.  Simply enter in your information to find your dress size!

Dress sizes

The fashion industry doesn't make this easy on a girl. You'll find that every brand measures its dress sizes differently. A 12 in one brand could be a 16 in another. The only way to really know is to try the dresses on yourself. It might be scary, but you won't be the first crossdresser to grace the store. Your other option is to buy your items online with En Femme. En Femme offers a generous returns & exchanges policy should an item not fit right - we also offer personalized fit guidance - just send us an email or call us and we’ll help you find your size.

Casual clothes, elegant style

Girls don't just wear dresses, of course. We offer a collection of tops and bottoms that can suit any occasion.

A crossdresser wearing a bodysuit

If you're shopping in-store, a good rule of thumb is to go one or two sizes up from your male clothes.

Shoes or Heels

It's a similar story with shoes. For US sizing, women's shoe sizes tend to be one and a half or two numbers larger than the corresponding men's size. For instance, a size 10 in men's should look for an 11 1/2 or 12 women's shoe.

Heels for crossdressers

How should a crossdresser dress?

A crossdresser should dress in the way that most empowers them, satisfies their sense of style, and nurtures their feminine instinct. There're endless sources of inspiration out there and there's no one "right" way to do it.

Who invented cross dressing?

Cross dressing's history is the history of all humanity. Ever since we put ourselves into the boxes of male and female, we've been finding ways to escape (or at least have some boundary-pushing fun). So it can't be credited to one individual, but rather a deep and indeed sacred impulse. A simple search will give you tons of examples of crossdressers from history; some of them will undoubtedly surprise you.

What is the difference between cross dressing and being a drag queen?

At its core, drag queens dress how they do for the purpose of entertainment and art, while crossdressers dress how they do for the purpose of personal fulfillment or identity. While there can be some overlap, it's important to understand that crossdressers aren't trying to put on a show; they're taking agency over how they present to the world and themselves.

Dive in with En Femme

Whether you're experienced or just beginning your cross dressing journey, En Femme is the premier shop for all things cross-dress. You'll never know until you try, and there's so, so much out there to try. Take a look at what's  new in the shop for fresh looks.


  • Sherry

    Since I was little (like 4-5), I’ve played around with crossdressing. Now that I’m in my late 50’s, I don’t give a bit of care. I’m full time.

  • Donna Bowser

    I have been crossdressing from 12 years old try some my mom clothes and high heels and her makeup. Then years for.

Leave a comment

Please note, comments must be approved before they are published