Why Do Men Crossdress? Reasons, Styles & Confidence Tips

Men crossdress for many reasons; comfort, fashion, self-expression, stress relief, role-play, performance, or to explore gender. For some it’s romantic or erotic; for others it’s purely aesthetic and relaxing. There isn’t one motive or identity that fits everyone, and reasons for ‘why do men crossdress’ can change over time.

Wigs, knickers, stockings, suspenders and corsets – if these are regular items in your closet, then you’ve come to the right place!
 
Whether you’ve been crossdressing longer than Lady Bunny or are looking to learn more about it, we’re here to give you a crash course on crossdressing!
 
Read on to learn more about the reasons why do men crossdress while maybe even getting some inspiration to broaden your own wardrobe!

Why and What Is Crossdressing? (Quick Definition & History)

Crossdressing has been practiced throughout history, in different societies, and for many reasons, but is basically the act of someone wearing clothes designated for the opposite sex.
 
This is separate from sexual orientation since crossdressers can be asexual, straight, gay, queer, bisexual, or have any other sexual orientation. Additionally, crossdressing is not an automatic indication of someone’s gender identity.
 
Over the years, society has definitely come a long way in accepting crossdressing and its many reasons from gender expression to personal preference.
 
And while there are a few forms of crossdressing, we’re going to focus on the reasons why men (whether assigned or identifying) crossdress in feminine clothing. 

Reasons Men Crossdress?

Emotional Reasons for Crossdressing (Comfort, Confidence & Relief)

One of the main reasons men crossdress, is for the emotional connection they feel with the practice.

It’s a way to express your gender or feel more connected with your authentic self. To some, it may even serve as a way to explore different societal norms and may lead to a path of self-discovery.

It can also act as a ‘release’ from the pressures of everyday life as a man.

Men may also feel powerful or most themselves when wearing female-designated clothing.

Crossdressing for Sexual Purposes (Consensual Adult Contexts)

Crossdressing can also be used for sexual purposes, whether it’s bedroom roleplay or a personal kink!
 
For some men, it’s thrilling to wear lacy lingerie or to embrace their femininity. It can not only be a turn on to wear the clothing but to also embody something that society has deemed “taboo”.
 
And there is absolutely nothing wrong with doing what makes you feel comfortable in a safe and fun way!

Crossdressing as a Form of Expression

Another one of the many reasons why men crossdress is as a form of expression!
 
Whether it’s a political statement, cultural tradition, drag performance, or a comfort choice, crossdressing is a way to express who you are beyond who you’re supposed to be.
 
Drag in particular is one of the most notable and popular forms of crossdressing, especially with all of the sickening queens dominating the globe on television right now! But, it’s worth noting that drag itself is a separate performance-based artform and isn’t the average method of crossdressing!

Is All Crossdressing the Same?

We’re only going to say this once: NO!
 
There are so many different reasons why men crossdress and there are also countless styles associated with cross-dressing from modest to more intricate variations!
 
No matter how or why anyone crossdresses, they are all valid!

Flamboyant Crossdressing

This is the most notable form of cross-dressing people are familiar with. It can include not only wearing feminine clothing, but also perhaps some makeup, wigs, or padding to create a more detailed feminine look.
 
This is also a great way men show their pride, whether it’s a part of a performance or part of their daily routine!
 
However, it is definitely not necessary to put on pounds of makeup like Trixie Mattel to show off your crossdressing pride!

Subtle Crossdressing

This more casual form may include wearing women’s underwear, tight jeans, or light body padding to display femininity in a modest manner.
 
Crossdressing in this way with a few feminine items could be used by men as a stepping stone to get started with crossdressing, or it could be someone’s normal preference!
 
Stilettos and bras are awesome any day, but crossdressing is still valid without them!

Mixed Dressing

Gender is not binary and neither is the way men dress!
 
Crossdressing for men doesn’t have to be only presenting as female, it can mix both genders for a unique and personal experience. Some men can also even feel most themselves when embracing both their masculinity and femininity at the same time.
 
This can include having a beard while wearing a dress or wearing a rugged leather jacket with a floral skirt (as long as they match of course)!

Crossdressing IS Dressing

All of the reasons why men crossdress and their own unique styles are not only completely valid, but they are also more than welcome here at Tiffany Hart!
 
Whether you’re looking for the perfect lingerie for a kinky night or the best corset for going out with friends, we have everything you need!

 
Why do you crossdress? We welcome any feedback in the comments section to help us grow as a community.

If you are looking for some new lingerie, we also encourage you to check out our latest sales and join our newsletter for updates on new stock and discount codes!