Women have it lucky. In the clothing department. Men are restricted to pants and shorts where as women get pants, slacks, culottes, shorts, skirts, skorts, mini-skirts, maxi-skirts, dresses that fall above the knee, below the knee or drape all the way down to the floor. So many options to choose from. Oh yes, how could I have forgotten. Men also have knickers.

Given all the choices, I assumed women had it easy finding something stylish and flattering for any occasion. And if it was easy for women, how hard would it be for me? A man who is used to much fewer choices and therefore less discerning.

Dressing for a Crossing

For a recent vacation, my husband Charles and I joined some friends for a transatlantic crossing on the Queen Mary 2. There are several formal dress nights on board and Charles and I thought it would be fun to tweak convention and go in drag on one of the nights. Our drag characters, Bobbi Roberts (me) and Frances Charles (Charles) are glamourous women – American heiresses of an uncertain era who enjoy a grand lifestyle and collect husbands and lovers who can afford it. Doing drag on a luxury ocean liner was going to be a moment of “shock and awe.” What we didn’t want, was so much shock that we were set adrift on a lifeboat to find our own way back to America. The night of the masquerade ball seemed like the best opportunity to challenge norms while not rocking the proverbial boat.

In May we set out shopping…

I’m a Size What???

Men’s clothing is remarkably forgiving in the size department. Yes, your pants scale up along with the measurement of your waist, but many shirts are now in the simple language of S, M, L, XL. Beyond that is XXL aka 2X as well as 3X. At my current weight and body shape, I’m usually in the XL or 2X department. Women’s starts with 0 and goes up, usually in even numbers. My understanding is that 14 is about where “plus” size begins and it goes up from there. As a 2X man, I dreamt of being a 16 or even an 18. Somewhat small but still understandably larger due to my gender. Instead, I found myself not able to look at anything smaller than a roomy 22, with a 24 as a more optimal fit.

Ok, so we’ve got the size range identified. Now can we find the dress?

Where Do I Hide My Upper Arms?

I’ve yet to find men’s formalwear that intentionally exposes décolletage, reveals shoulders or upper arms – our choices are a jacket and trousers with a choice of number of buttons and -- contain your excitement – single or double-breasted. Few men’s jackets have any variation in length.  No thought is given to where the waist falls and how it might change the way you look, let alone what’s happening around the neck and shoulders.

Given my broad shoulders and larger upper arms, it was quickly decided that I needed to be in a dress with some sort of cap on the shoulder if not a sleeve of some length (again, guys, imagine choosing whether your tuxedo has a cap sleeve or goes the full length of your arms…).

My Turn in Empire


No, not the TV show, an empire (pronounced: ahm-peer) waist on my dress. It can be flattering on some women with the right figure.

It did nothing for my figure except make me look pregnant.

Next came a dress that had a belt – there’s nothing like a belt to help draw attention away from your “problem areas.” I tried on one dress. I liked the color a lot – a great shade of blue that I thought would look great with the red wig I was planning to wear. The little belt that was part of the dress also looked flattering. It seemed to magically even out my proportions. And then, it slid below my stomach. That highlighted the one area I really wanted to avoid seeing - my stomach. And my stomach seemed even more prominent than before. As if this piece of fabric belt was lifting my belly up and crying out “look at me, look at me!” If I didn’t look pregnant in the empire dress I certainly felt like I looked it in this one.



If you want to look good, you need to spend a little money. After several unsuccessful attempts at online discount dresses from China, we realized that if we wanted a good dress that was going to flatter and look right, we would need to spend a little more. Fortunately, we were shopping in late May, right at the end of prom and formal season so there were plenty of dresses on markdown. Thank you to all the high school juniors and seniors, sorority sisters and other glamour girls that made other selections, we found our winner at Nordstrom online. And it was half price!

Pulling the dress out of the box, I could tell this was the one. There were sparkly things all over it, reflecting the light and giving it a shimmer. I unzipped the back and stepped into it, taking care not to step on the lining. I pulled it up, slipped my arms through the arm holes, short cap sleeves covered my shoulders and gave an illusion that my upper arms were a bit more demure than they really are.

I had that “when you know, you know” feeling. This was the dress. It just felt right. And with the help of a Colombian body shaper and some D-cup silicone inserts, I was given the extra assist I’d need to fill out the dress.

Most Glamorous

Photo by    Daniela Buda

My debut at the Masquerade Ball was a hit. Escorted around during the Masquerade Promenade, my companion and I were awarded “most glamourous couple.”

As I sipped on the champagne I received as my prize, I reflected on the journey to get to that moment. Countless dresses tried on, what felt like days practicing walking in 4-inch high heels and hours applying make-up to complete the gender illusion. It was all worth it and I’ll do it again in a heartbeat. But the one thing I’m not excited about is facing the repeated disappointment in the mirror shopping for the dress. Maybe women aren’t as lucky as I thought?

What’s something you’ve tried and realized afterward it wasn’t all that? Let me know at rob@ignite-360.com

Header photo by Daniela Buda