While attending UCLA in the 1980s, I occasionally modeled for fashion designer friends. I was a professional athlete with no body image shame, thus I was draped in everything from power suits to Madonna-esque exterior lingerie with combat boots. I think of clothing as being unisex rather than gender coded. It's all about context and confidence.
That said, for many years I alternated between two "daily" looks that were tailored (no pun intended) to either my bike racing team's sponsored looks (heavily branded with logos and such) or my music business tasks that demanded a creative-yet-professional style, suitable for inspiring confidence in a Rock band *and* in executives at labels like Interscope and Warner Bros. When the pandemic lockdown hit, I lived in yoga pants and T-shirts until I snapped into YOLO (you only live once) mode. Even when working remotely with no clients present at the recording studio, I began "dressing the part" again, and I stopped saving my finest threads for "special" meetings or occasions. Figured I might as well enjoy the nice stuff before I'm dead.
My wife noticed that I was dressing more intentionally, so in 2023 she suggested I buy a kilt. (She's part of a Scottish clan.) I liked it enough that I now own six, including a custom bespoke heirloom-worthy piece by Barb Tewksbury, who wrote The Art Of Kiltmaking. Rather than "getting comfortable with the idea" of wearing a skirt in public, I just "went for it!" on day 1. Styled it with a Rock 'n' Roll T-shirt and tennis shoes. No sporran, no kilt hose, no bagpipes. Just like styling jeans, but substituting a kilt... Got a lot of vocal attention from women who ignored the fact that my wife was literally standing next to me as if she were invisible. Fortunately we were amused by it. Dudes inquired if they could pull off the look, to which I replied, "Only if you're not shy because folks will want to learn more."
Fast forward to 2026, and I'll wear anything in public that fits me well and feels good on my skin. I frequently wear structured midi skirts and occasionally straight cut sweater dresses and T-shirt dresses, always in solid (not patterned) colors, offset with male gender coded shoes, jackets, hats, watches and facial hair. I avoid frilly and "girly" garments because : a) they are not "me" and b) as much as i love women, I have no desire to look like them. I sometimes wear pants, sometimes structured shorts with hosiery, like argyle or colored leggings/tights. Anything goes, provided it amuses me and looks cool on me. Heck, I'd even wear a table cloth if I thought it would create a stylish silhouette!
Anyway... It seems that some members of the group might benefit from my experiences as a male who projects masculinity, who will wear whatever the heck I like, with total confidence, amusement, and...whimsy. The key ingredients for my effortless ease in wearing skirts and dresses while "always presenting as male" are: 1) my clothing fits well, 2) I like its silhouette, 3) I stand up straight with good posture to project confidence and intention, 4) I dress appropriately for a desired outcome (such as acknowledging the difference between pitching a venture capitalist vs. working with creative artists in a recording studio), and 5) I allow one "statement piece" (in this case the skirt or kilt) to shine in the spotlight without competition from other parts of the ensemble.
Hopefully this post will encourage other members to take a leap of faith and express yourself to the world in a manner that gives you joy. Let me know how it goes!
