My Boyfriend Wears Dresses (7 Things To Do When Your Boyfriend Likes To Wear Dresses)

Traditional masculinity states that a man needs to put on pants, jean trousers, slacks, shirts, and suits. Regular masculinity means a man with beards, bristles, or a sexy five ‘0’ clock shadow. According to modern society, a manly man can pull off masculinity without the help of earrings. 

As such, it is unsettling to see a guy wear skirts or dresses unless he claims to be transgender or bisexual. It is usually difficult to accept that a man who used to dress in manly clothes isn’t confused about his gender identity because he started wearing dresses. 

When you’re the woman who gets to date, love, and constantly sees that man, you’d have your worries. Yet, it doesn’t change the fact that you care about him even though you’re confused about the development. 

Did your boyfriend recently tap into his feminine side, and now wants to cross-dress? Are your boyfriend’s recent cross-dressing escapades making you question or reconsider your view and tolerance of the LGBTQ community?

Only your man knows his reasons for the switch, and you won’t know them until he tells you. This article might help you answer the troubling questions you’ve been harboring since you discovered that your boyfriend likes wearing women’s clothes.

7 Things To Do When Your Boyfriend Likes To Wear Dresses

1. Don’t judge him before you’ve heard his reasons

The first thing that would probably come to mind when confronted with a cross-dressing partner is, has he recently discovered he is internally a woman? Followed by that are the questions: will he want to be a trans now? Will he get estrogen hormones injected into him so he can become a she? Will he have breasts like me?

While it is normal to raise these questions in your mind, you’ll only drive yourself crazy with the million scenarios your mind will imagine. Rather than having preconceived answers or hating him, listen to his side of the story. Let him tell you what his fascination with dresses and female clothing is. After that, you can form your conclusions.

2. Keep an open mind during the first discussion

Just as preconceived opinions are unhelpful, coming to the first conversation on the matter with a closed mind won’t help either. Except your relationship was already on the brink of a breakup, don’t conclude that you cannot continue dating your man because he’s now a crossdresser.

There are so many cross-dressers who wear female items such as a skirt and a dress just because they have fun doing so. Whether your boyfriend is a guy wearing a dress for fun, or it’s the beginning of a new sexual identity, you still need to hear his thoughts. 

Let the love you have for him guide your thoughts towards openness so that both of you will leave the conversation with clarity and empathy.

3. Process your feelings about the new development?

process your feelings about the new development

Your boyfriend’s discovery of his love for dresses is as much your concern as it’s his. Therefore, you should think about the impact his cross-dressing desires are going to affect you mentally, your sexual connection, and your interaction with mutual acquaintances. How do you feel about his newfound hobby? Are you okay, hurt, confused, angry, or even indifferent about it?

Acknowledging and naming your emotions will help you process your thoughts before having a big conversation with your boyfriend. Whatever you feel is okay, just be sure you’re empathetic towards your man. He might or might not be sure of why he’s drawn to women’s clothes. Lashing out at him out of raw emotions won’t help either of you.

4. Does he want to be a public cross-dresser?

Now that your feelings are on a relatively neutral level, you can have the dreaded conversation. Get your boyfriend to tell you exactly how he feels, without holding any truth back. How long has he had the desire to cross-dress? Was it before or while dating you?

Is the cross-dressing thingy an eroticroleplaying idea that stimulates him sexually, or is there a gender-identity conflict? How does what he wants to wear underneath his pants affect his masculinity? Asking and getting answers to these questions might rouse some uncomfortable feelings, but you need to do it for your peace of mind.

5. Support his decision

After asking the tough questions and hearing his answers, you should try to be supportive of his decision. You may not completely agree with his reasons, but you can be okay with the fact that it’s what he wants to do. If he holds you and your opinions in high esteem, it will mean a lot if your support is genuine.

Again, it might take a long time before you stop cringing at going out with your boyfriend clad in a skirt and blouse. Once you’re used to it, all you’ll see is the wonderful man who remains under the clothes.

6. Don’t force yourself to enjoy his new fetish

dont force yourself to enjoy his new fetish

If you love him so much and want to still keep the relationship, you should try to understand his avid interest in exploring his feminine side. However, that doesn’t mean you should do what you’re not comfortable with.

It will take a while for you to get used to seeing your man in lingerie, skirts, or dresses. Give yourself that time without feeling guilty for taking so long to get used to him. He should understand that it’s a lot to take in, especially if you’ve never been attracted to a woman before.

Encourage him to switch up his former masculine way of dressing with the new one. That way, your mutual efforts will keep things balanced.

7. Separate on a mutual basis in case of incompatibility

At the end of the day, you cannot force yourself to like what you hate. If you’re the kind of woman who is only attracted to a mustache-bearing man in leather clothes, no amount of convincing will make you like a man in skirts.

If your desire can only be inflamed by a clean-shaven man in a powered suit, a man in a dress won’t hold any allure for you. Nobody will blame you for no longer desiring a man who once wore the kind of outfits that turn you on. 

It is best if you continue to have sincere open-minded conversations with your cross-dressing boyfriend. So that if a breakup is the best option, it will be an amicable, rather than embittered one.


Is it okay for a man to wear a dress?

Yes, it is okay for a man to wear a dress if that’s what makes him comfortable. After all, medieval men wore gowns and feminine-looking outfits. 

Why does my boyfriend dress like a girl?

Your boyfriend wears girls’ outfits either because he is fascinated by them, or he feels he’s more of a woman than a man. Putting on women’s clothes could be the beginning of his transgender journey. 

Why do men love sundresses?

Some guys love sundresses because they enhance a woman’s femininity, while others do so because their women look very good in them.

How should a man dress as a woman?

A man can comfortably dress as a woman by including the pieces that fascinate him the most. That could be something as simple as hooped earrings or a skirt.

What does it mean when a man dresses as a woman?

It could mean anything from a mere fascination that will fade with time, to a full-blown desire to become a woman through a transgender transition.


Before concluding that your boyfriend is going through a midlife crisis or suffering temporary madness, ensure you talk to him at length to know where his head is at. Afterward, you may decide to stick with him despite his new fascination with women’s outfits or leave him for ‘your version’ of a man. You’re entitled to your desires, just as he can wear whatever he likes.

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