The term cross-dressing is usually used (but not always) to refer to cisgender, heterosexual men who wear clothing and accessories that are considered feminine or associated with women.

Folks might cross dress for fun, for political motives, for sexual reasons, or to entertain.

They might dress that way full time, occasionally, or only in private.

I think most of us here on this forum are part time but would probably dress more if we could?

The rationale for cross-dressing isn’t universal and there's limited research on common characteristics among those who do cross-dress.

The Author may find Forums and blogs useful and surveys which give a pie chart result into the many reasons why we cross dress.

Cross-dressing itself isn't considered pathological (of or pertaining to a particular diagnosis or disorder).

However, people who cross-dress may experience societal backlash for resisting gendered expectations.

While some people who cross-dress may experience guilt, many don't, and a way to support someone who cross-dresses is to emphasize that it’s a form of expression, not something that an individual needs to overcome or resist.

Ways that people choose to express gender may change over time, so someone may find that over time cross-dressing no longer meets those needs or interests, but for others, cross-dressing is a lifelong practice.

I think for most its a life long hobby or calling but will I still cross dress if I don't think I look good?

Before diving in, it might be helpful to understand more about gender, sex, and societal expectations around the two. Sex is how people are classified at birth, based on their genitalia and chromosomes.

This upsets some people but for me this is an absolute in terms of the genitalia you're born with.. A baseline we need to star with.

Usually they’re split into the categories of male or female based on these traits, but genitalia and chromosomes vary, so not everyone falls cleanly into one group or the other.

Gender, unlike sex, isn't biological.

It refers to the characteristics that societies define as being associated with men or women, and it doesn’t necessarily align with a person’s assigned sex at birth.

This needed saying to alleviate the baseline at birth above..

Gender is an undeniably salient force prevalent in society.

Gender roles dictate how people are expected to dress, act, and feel, and these are reinforced at a young age for most folks.

You might have grown up learning that there are two genders — men and women — and that each of the two categories have certain characteristics associated with them.

We're all brought up this way.. I think things are changing and people have more choice and knowledge.

People are taught, explicitly and implicitly, that these distinctions are real and concrete, so it’s no wonder that you’re feeling concerned about the idea of cross-dressing.

Men must do and act as men..

However, some reframing might help to consider gender play and cross-dressing in a new light.

Although gender is often discussed as a binary (men or women), many report identifying with gender on a spectrum.

Cross dressing is on the Trans spectrum.

While some may feel that their identity aligns easily with one end or the other, many folks might find themselves somewhere in the middle.

Those who feel that their gender aligns with their sex assigned at birth are often described as cisgender.

For some, this isn’t in alignment, and as a result they may identify as transgender (often shortened to trans), gender non-conforming, non-binary, gender-fluid, a-gender, or two-spirit, among other terms.

This experience sometimes leads to gender dysphoria, which is defined as significant distress as a result of dissonance between gender identity and sex assigned at birth and is a recognized condition in the Diagnostic and Statistical Manual of Mental Disorders (DSM-5).

Experiencing gender dysphoria can lead people to change their gender expression or even alter their bodies so that they better align with their identities. Identifying as something other than cisgender doesn't necessarily mean that someone will experience dysphoria, however.

Some might identify as cisgender but realize that they don’t agree with all of the expectations that come along with their gender, and some might find that their gender experience shifts and changes over time or depending on the context.

Other people, like many cross-dressers, may feel that their sex and gender align, but still might want to explore and enjoy aspects associated with another gender.

Now that you’ve got a primer on gender, hopefully it’s easier to recognize that high heels, dresses, and makeup aren't inherently “female.” Just because the larger society associates certain articles with femininity, and someone choosing to wear those items doesn’t necessarily communicate anything about a person’s gender or sexual identity.

Society that's the word.. Society says that's men's and those are women's.. This is the women's department the mean department is in the basement..

It's also key to point out that people who cross-dress generally don't consider themselves to be a different gender from the one they were assigned at birth.

That's most of us here on the forum?

For example, a cisgender man can wear a dress and identify that he’s cross-dressing.

However, if a trans woman is wearing attire that’s associated with women, this can be a way to express her gender through her fashion choices.

Whether a person’s clothing choices reflect their gender identity or not, the gender identity of that person is real, valid, and deserves respect.

Gender is a complicated subject, but it doesn’t have to be scary; exploring it can be challenging, exciting, and liberating.

Having a loving, open partner to take the journey with could make a huge difference.

It most certainly does but can be very scary for them. And we feel guilty for putting them through this.

Asking questions to better understand their gender experience, getting involved in gender-related activism, standing up for them if they’re facing discrimination, and being there to support them when they need it are just a few actions a person can take to be there for their cross-dressing partner.

If you find a partner willing to be part of your crossdressing you're very lucky and I'd say if you're a partner of a cross dresser have fun with it.

Reading up more on the topics of gender, gender expression, and gender diversity may also be helpful.

Organizations such as the Human Rights Campaign and GLAAD may be helpful places to start..