Today, we welcome JeffB from Southeastern Pennsylvania to Profiles of Beskirted Men!
What is your name?
JeffB
Where are you from?
Southeastern Pennsylvania
Which types of gender non-conforming clothing do you enjoy wearing?
Skirts, dresses, tops, shoes, outerwear, underwear, sleepwear, tights (in winter), jewelry
When did you start wearing gender non-conforming clothing?
I’d say around 1980 when I started wearing my mother’s dresses (in secret, she never knew) and liked it because I looked good in them, and that made me want to wear her clothes more and more. By 1991, I actively begun crossdressing and joined a local crossdressing group for a few years.
How did you start wearing gender non-conforming clothing and why?
Actually, it all began with shoes, not clothing. When I was thirteen, I was insanely curious about how women, mainly my mother could walk in high heels. However, being too afraid to ask her how she managed that feat, I sought my answer in the only way I could….by wearing her shoes myself. One day during summer vacation while she was at work and I had the house all to myself, I put on a pair of her pumps (fortunately, we wore the same size) and conducted my experiment. It took a few tries just to stand in the three inch heels, walking took a while longer as I stumbled and staggered around like a drunk leaving a bar at 2 a.m., but I eventually got the hang of it and discovered it was FUN! Every chance I could, I’d sneak into mom’s room to wear her heels because I loved it. Years later, curiosity got the better of me again as I wondered what it was like to wear mom’s dresses with her shoes, when I did, I liked what I saw, and the rest was history.
What is your motivation now for putting on gender non-conforming clothing?
Strictly enjoyment, it’s the best possible reason. I just LOVE wearing the clothes.
What do gender non-conforming clothes mean to you?
For me, it means being able to escape the narrow, constrictive norms required of men in regards to their dull, boring clothes. When I wear skirts, dresses and heels, I feel bold, free and empowered, it’s intoxicating, the joy I get from being in womenswear, what with the bright colors and soft, flowing fabrics is indescribable as it enables me to express myself in ways I never knew were possible. In fact, it wouldn’t be exaggerating to say that wearing women’s clothes helps me tap into my inner femininity, and that feels good.
How often do you wear gender non-conforming clothing?
I’d say three or four times a month for public outings. I’d like to do more, but work and life often gets in the way, however, most nights, I sleep in full slips and nightgowns.
Do you go out in public dressed in gender non-conforming clothes? If not, why not? If so, how often and where do you go? Are there any places you wouldn’t go?
Oh, yes, I do go out dressed in public as staying indoors is a waste of time. A usual outfit is a top with a skirt, or a dress with heels (or flats), earrings and a handbag. As for places I go: downtown in the city where I live, shopping malls, movie theaters and museums. I enjoy being among crowds of people on my outings.
Do you find it hard to go out in public in gender non-conforming clothes?
No, not at all, for me, it’s easy, I do it all the time. I mean, at the end of the day, it’s just clothes. Nothing more complicated than that.
What is your best and/or worst experience in gender non-conforming clothes?
My best experiences in non-conforming clothes are every time women compliment me on my attire, and those interactions I have with them are genuinely honest. One woman actually said I looked better in a dress than her, that meant a lot to me. Heck, there’s even been rare occasions when I’ve had men say nice things about me. As for a worst experience, other than having a car full of guys laugh at me in passing, that’s pretty much been it.
Do your family or friends know about how you dress?
That’s a no on both.
Are there people you don’t want to know about it?
Family and friends.
Does your partner accept your clothing choices?
I live alone, so that’s not a concern.
What is your favorite style?
I like to look classy and stylish, even when it comes to casual wear because I always dress to impress. As a man who wears women’s clothes in public for all to see, it’s important to look proper and tasteful, not clownish or outrageous.
Where do you shop for your clothes?
Several places: Old Navy, JCPenney, H&M and the discount department at Macy’s. I buy all my clothes in person so I can gauge on the spot what looks good and what doesn’t, what works and what won’t. The only thing I buy online is footwear because it’s impossible to find size 13 women’s shoes in brick and mortar stores.
Is there anything else you would like to add?
Life is too short to deny yourself the pleasures you enjoy. If you want to wear non-conforming clothes, go for it!
Thank you for sharing, JeffB!
If you would like to have your profile featured in Profiles of Beskirted Men, take a look at the post I wrote about it for more details.



Hi Jeff!!!
It’s great to hear from you. I used to frequent Skirt Cafe and lived your posts. You made so much sense and had just such a zeal for life and living your true self that I couldn’t wait for your posts. Sadly, the politics there drove me out but it so so nice to see you here. Would love it if you dropped by our forum Men’s and Unisex Skirts at Delphi (https://forums.delphiforums.com/n/login/login.aspx?webtag=dflogin&sb=y&seamlesswebtag=%2fMensSkirts%3fredirCnt%3d1)
Take nothing away from Alex’s site here which is wonderful, I’d just love to get your take on some of the outfits I post there. Cause you got style my friend. And I think you could help me do better. There are a bunch of guys there who have already helped me immensely but I always think more the merrier. Especially when we’re challenging the status quo.
My biggest challenge is the thing you’ve already mastered; your look. I’m still experimenting with different combos cause I find you shouldn’t just substitute a skirt where you wore pants/shorts. It actually takes more effort and being new at it, I feel like I miss more than I hit.
Well, even if you don’t drop by, great hearing from you and keep being the amazing ambassador that you are.
Thanks for the response. I’ll swing by as soon as I can. I’m honored that you’ve asked me for fashion advice. I’ll try to help in any way I can.
Thanks Jeff! To me, youre kind of a legend cause you wear what you want out in the open and are free, unassuming and you dress well.
I have a few online friends who share my take on MIS. Namely, anting t wear a skirt as a man, presenting as a man and not wanting to be a woman.
I forget your tagline on skirt cafe but I remember really loving it. Something like “I don’t want to look like a woman, I just want to wear their clothes”. Or something like that. Which I thought was perfect
Nice to meet you Jeff, so you basically started living free by the time I wasn’t even in my mom and dad plans, I can only wonder whether it was difficult back 30-40 years ago, or do you see other people mindset changed when the interactions happen.
Indeed you are paying attention to overall look – while men’s clothing is really boring, I feel like women actually start to follow this generic trend with black tops, baggy trousers and quite similar make up with focus on the eyebrows. We could tell something similar about modern femboy movement with black and white stripes everywhere but at least here the population is smaller and still doing edgy things from “normal male” pedslżh
Mateusz: Thanks for writing. To answer your question, I’ve only been wearing women’s clothes in public for the last fifteen years or so, but, I would imagine there was probably less in the way of tolerance three decades ago. I consider it important important to look my very best while in womenswear to present the best possible image of men in skirts and dresses.