Profiles of Beskirted Men: JeffB
July 21, 2025

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.

How would you rate this post?

About the Author

Alex Seifert
In many ways, Alex is a typical man who just so happens to enjoy wearing skirts and high heels. He is married to a wonderful, supportive wife and has a young son. His hobbies include reading, programming, metal music, playing instruments, video games, cars, hiking and a number of other smaller things.

Related Posts