Ask Hannah!

I am a guy of 59 and I have for a number of years now been wearing “female” clothing as part of my everyday wear, e.g skinny jeans long before they where available for men. I have also used leggings for quite a while and lately I have bought a few body con dresses. Dresses I do not wear in public, but skinny jeans, leggings, platform sneakers etc is part of my natural wardrobe.

Why, one might ask? Am I a cross dresser is another question? I am not sure myself, I do love women clothes as they are so much more comfortable (typically) compared to men’s clothes and that has been my main reason for wearing them. I am bald, I have beard but I do make up from time to time as I feel that color is fun but I could never pass as a woman (I think). I have never seen myself as a cross dresser but when I read your guide to cross dressing I started to think, absolutely not in a negative way but more of curious way and just wanted to reach out to see what you think.

I don’t think there will ever be (and I don’t think there should be) a set of universally agreed upon parameters and standards and requirements that, ah, absolutely classifies one’s gender identity or qualifies someone to align themselves with a certain label.

Are you a crossdresser? That’s up to you.

You might be a man that likes to wear dresses and leggings. Again, it’s up to you.

I think for some of us it might come down to how you view an article of clothing. Is it a dress or is it a woman’s dress? Are you wearing jeans or femme jeans?

On a side note, I think it’s kind of funny when department stores have sections named “Women’s Dresses” implying there is a section somewhere in the store for “Men’s Dresses”.

Gender identity is a highly personal choice and not one that needs anyone else’s approval or understanding. I work for a college and I work with many, many students with different lives and experiences. I’ve worked with girls who wear beautiful dresses who use they/them pronouns. It’s not what I expected from someone from someone who is (presumably) cis and dresses extremely feminine.

Gender identity and labels can change over time. I was crossdressing for years before I even knew of the word’s existence. I identified as a crossdresser for decades until I embraced identifying as transgender and, more specifically, bi-gender.

I mean, I am still a crossdresser. When I present as male I am wearing panties. I wear leggings and femme jeans in boymode. In a way how I identify is largely tied to my overall gender presentation… and it can change throughout the day. For example, last Saturday I woke up and stayed in my nightgown drinking coffee. I was in boymode… but wearing a nightgown. So, my overall presentation was BOY but I was wearing “girl clothes”. So, by my own definition, I was crossdressing. I then got ready for the day and I was in full femme presentation and I was no longer crossdressing. I was (and always am) a transgirl presenting as her gender identity. After my day I returned home, washed off my makeup and put on panties and boy jeans and was in boymode. So, I was once again crossdressing.

Does that make sense?

Some of us feel the need to identify as SOMETHING (and I totally get it) but some of us don’t. Don’t overthink it, don’t force yourself into a box or a label simply for the sake of having a word for who you are.

So, are you a crossdresser? It’s up to you. If you are interested in my perspective, I chat a little about this topic here and here.

Love, Hannah

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7 thoughts on “Ask Hannah!

  1. I present as male while completly dressed in women’s clothes, just no dresses or skirts. I have colored nails and wear high heels. And some days mascara. Am I crossdressing? Or am I crossdressing when I (rarely) wear “boy” clothes? I don’t worry about this
    I refer to this as blending.


  2. I love this advice! You are what you think you are, and that’s all you ever have to be. This is great advice, no matter who you are or what you’re doing. As a cis female, I am simply more comfortable in men’s jeans, the occasional men’s boxers to sleep, and men’s packs of “wife-beater” t-shirts on certain vacations. I never thought of this as crossdressing, and find it interesting that other people would. I have always considered it comfort-dressing. I also find it interesting when people consider it crossdressing when a man wears makeup and nail Polish. I consider that the adornment of their person (this boy George or Billy Joe Armstrong). The reality is, people don’t consider it anything when a woman doesn’t maintain her eyebrows, let’s the peach fuzz grow wildly because that’s what her hormones create for her, and have short undecorated nails. Why is a guy who does these things considered anything but a guy who wants his eyes to pop and his nails to be pretty anything other than just wanting to be? To me, I understand the need for labels overall, but I never understood the anxiety that comes with them. For me, the label is less important than the feeling of “you-ness” that you feel when you are dressed in the way that makes you feel the most you. I guess this is borne from being referred to as a “tomboy” most of my life. There is no heteronormative clothing, in my opinion. If I want to wear t-shirts and fatigue pants with military boots, how is that any different than if I wanted to wear a skirt, other than society thinks I should? If a male wants to wear a lacy top, a skirt, and can wear heels without face planting, I say go for it… and can you teach me how not to fall as soon as I stand in heels?


      1. lol walking in heels has everything to do with balance, momentum, and keeping your back straight and head held high. Just strut.

        Love, Hannah


      2. I think it also depends on the type of heel. I’m ok in stupid-tall, somewhat chunky heels, but the second you are talking about a small heel or a stiletto, I’m done. My ankles rebel and I’m on the floor. So. Many. Times. I’ve seen a 6’3” man (who identified as a man) try on my heels because he thought it crazy my feet were so big, and as his first time in heels, rock it. The heels he tried were the silly stilettos my sister forced me to wear at her wedding and I had fallen (shock). He looked like Naomi Campbell, strutting, looking amazing, and even did the stop-half turn-hip pop before laughing and taking them off. Really? All my ankles could scream was “fine. He can wear those, you take his loafers” 😂

        Liked by 1 person

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