Profiles of Beskirted Men: Tommy J
September 24, 2025

Today, we welcome Tommy J from Portland, Oregon to Profiles of Beskirted Men!

What is your name?

Tommy J

Where are you from?

Portland, Oregon

Which types of gender non-conforming clothing do you enjoy wearing?

skirts, leggings, ballet flats, strappy sandals, sundress

When did you start wearing gender non-conforming clothing?

age 11. my aunt is only a few years older than I am and when she went off to college she left behind most of her summer clothes and I tried every one of them on…over and over. then a family moved in next door and their daughter, Carole, and I were the same size and we tried on one another’s clothes. sadly, I could not wear her shoes.

How did you start wearing gender non-conforming clothing and why?

I had a trove of my aunt’s clothes to play with. initially, I got hard when trying them on, but as I aged I realized clothes are fabric and fabric is unisex. so wear whatever you want, wherever you want and whenever you want. like my manicurist told me when I was 30 and got my first mani/pedi: “it’s just paint”. clothes are just fabric so wear what you like and what makes you feel good.

What is your motivation now for putting on gender non-conforming clothing?

comfort and style

What do gender non-conforming clothes mean to you?

I live in the Pacific Northwest. it is a very liberal place and here there are literally thousands of people who cross gender lines. I am a guy. want to be a guy. not into wigs and makeup and breast forms. but I do love “women’s” clothing made from fabric that was intended to be worn by women and women only. but spend some time in a skirt or leggings and a pair of ballet flats and you will soon understand why women are always looking like that and enjoying the comfort built into most womens clothes.

How often do you wear gender non-conforming clothing?

pretty much every day I have on something made for women.

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?

I do to some extent. I have worn a kilt out and spend much winter time in leggings and go out running errands looking like virtually every woman I come into contact with. they have it figured out. comfort, looks, style. men are hogtied by machismo and mostly think they could never be caught dead in a comfy skirt and some t-strap thong sandals. they are missing out. period.

Do you find it hard to go out in public in gender non-conforming clothes?

no, not here in Portland

What is your best and/or worst experience in gender non-conforming clothes?

I have been praised and heckled. mostly praise, thankfully. and most of that comes from women

Do your family or friends know about how you dress?

some do

Are there people you don’t want to know about it?

yes

Does your partner accept your clothing choices?

yes

Where do you shop for your clothes?

mini skirt, sleeveless shirt, strappy flat sandals (nails painted, of course!)

Do you have any links you would like to share (i.e. social media profiles or websites)?

torrid.com

I buy shoes from them. cross-gender styles (flats, sandals, chelsea boots, cage-sandal heels, slides, clogs) and made big enough for most all men to enjoy. I have 13 pairs from Torrid and love them all! I wear a man’s 10.5 and have found that 11.5 from Torrid works perfectly for me.

Thank you for sharing, Tommy J!

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.

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.

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