The last thing I do before going to bed is look at the outfit I laid out on my valet stand earlier in the evening. It helps set my intentions for the day to come — sometimes even making a guest appearance in that night’s dreams. By morning, I sometimes change out a pair of shoes, socks, a belt or bow tie to more precisely suit my day ahead. I might be feeling a case of ‘the Mondays,’ but I’m dressed to step through the looking glass.

I’ve always had a sense of style, even if it hasn’t always been dapperly directed. It develops through phases and eras and self discovery.

Growing up on Long Island I had live-in style icons. My mom turned heads in her Elvira-like dresses and confidence. Dad wore leather pants and daishikis as a young math teacher, and rivaled John Travolta in his Saturday Night Fever stylings. It was my mom who taught me that over-dressing for an occasion is dressing for the occasion.

Before I leave home each morning — after I’ve garnished my outfit with the right pocket square, lapel pin, pocket watch, etc. — I take a few steps back and face the mirror. I gaze similar to how I used to stare at those Magic Eye posters back in the 90’s. I think, ‘what is the most ridiculous thing that someone can say about me in this outfit?’ “I see a schooner!” It prepares me with a softness and sense of humor to what could have otherwise been a hard and vulnerable shell.

‘Why yes, I am expecting to be invited to the Playboy mansion. Got my key right here just in case!’
‘Yes. The glasses are made of real Snozzberries.’
‘Regatta? Where?’
‘No, this outfit does not come with a red nose.’
‘Big Mistake. Big. Huge.’

First and foremost I dress for myself — how I want to feel. I wear my inner-dream-life unapologetically on the outside. It makes me feel authentic, honest, and fearless. Because I know that my style is gender-unconventional, while I keep my eyes bright and filled with the love of life I have within, I do sometimes keep an eye on the periphery to be safe. When my wife is with me that’s her job. I assume the best in people and that everyone will receive me with an open heart and mind. More often than not this is the case.

The moment I lock the door behind me I am left with the feeling that my concoction of the day connotes. I forget the details I culled together the night before and adjusted before leaving home. While I am left with a strong sense of self-confidence and awareness, I am not burdened by the insecurities of perfection. Once on an elevator ride at work my friend Jaclyn marveled at my outfit du jour. She said, “If I ever wore something like that people would say, Jaclyn – you don’t match.” I think I surprised her when I quipped back, “I don’t match. I just don’t care that I don’t match.” Sometimes you wear the suit. Sometimes the suit, well it wears you. Power clashing, pattern confusion, texture meshing, fashion transgressing — it’s all fine by me.

Last year I had the amazing opportunity to attend the first ever queer style program at the SxSW festival. The Queer Style: Visual Activism & Fashion’s Frontier panel featured thoughtful and inspiring trail blazers in the queer style industry — Anita Dolce Vita of dapperQ, Sonny Oram of Qwear, Leon Wu of Sharpe Suiting, and Aja Aguirre of Fit for a Femme. My wife Megan was invited to cover the event for Curve magazine.

Before the panel began, my buddy Leon introduced me to Sonny. Sonny said to me, “The first question on the panel will be ‘What is queer fashion?’ You should just stand up.” I didn’t realize that this panel and these relationships would influence my life so substantially and in understanding my style on more profound levels. I now have an appreciation of fashion as a means to influence social and political change. Visual activism is living your life out loud and taking those opportunities to educate, influence, empower, and challenge paradigms.

The truth is — every morning when I get dressed, there is an unspoken tension between what I’m expected by society to wear versus what I’m inspired to wear. That very tension drives me to confront those limitations within myself — set my own rules. When charting the unfamiliar waters of my own paradigm I need to have the sense of humor and security to allow myself to fail sometimes — and fail spectacularly! And I should be dressed for a regatta… on a schooner.

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