A Different Look

As my years of regularly going out dressed grows longer (nine years in October), my style continues to evolve. 

Early on, it was 1950’s housewife; dresses, hose, heels. Mind you, I still love dresses, hose, and heels–that will never change. I’ve just moved on to a more varied style.

My first sea change was pivoting to summer clothes. Summers, especially where I live in the Midwest, generally means sun and heat–and lots of both. Heat, wigs, and pantyhose are not compatible, and I could not imagine going out without pantyhose–until I realized I could. 

That was accompanied by the realization that if I wore a spaghetti strap top– and god forbid, showed my boy shoulders–the world would not end. One time I tried on a spaghetti strap dress, liked the look, and bought it. I realized I really loved summer dresses as much as the more traditional 1950’s look. 

I also found these styles, with a lot more exposed skin (those same bare shoulders), meant what I was wearing was a lot cooler, offsetting at least some of the added heat from wearing a wig. It also meant I had to up my shaving game–legs, arms, shoulders, and torso. 

I have a number of summer dresses now, and actually look forward to summer so I can wear them. This year I had an additional ten weeks of Australian summer, and a second source of summer clothing choices.

The next “why not” revelation was–as urged by my GG friend Renee–“to expand my comfort zones.” I ventured into the juniors departments of department stores, full of dresses aimed for those two generations younger than me, or to fun stores targeting younger demographics like Windsor, Akira, or Forever 21, or thrift stores like Plato’s Closet. 

Concurrent with this willingness to look (and try on and ultimately buy) younger styles, was my ability to shed weight and move from plus sizes to more normal sizes (right now, I weigh about fifty pounds less than when I retired in 2012).  I became skinnier (still not skinny, but definitely less chunky) and these styles became more flattering. The running and biking also meant my legs firmed up, and I’ve gotten compliments from my GG friends on how good my legs do look, and the younger styles tend to be shorter and tighter–and I like shorter and tighter (as my GG friend Ms. Dee-ism says, “Tina Turner short”).

A couple of years ago I saw a sequined dress at Nordy’s. It was an XL, and I knew I had to try it on. I knew I wasn’t going to any New Year Eve parties anytime soon, but I wanted the dress as soon as I tried it on, and bought it. Because of a combination of circumstances, I DID get to wear it on a New Year Eve’s night out, and again to the Fox Theater to see the musical Tootsie with my GG friend Karla.

From that one purchase, I now have about ten sparkly dresses, in black, red, blue, gold, silver, white, and shades in between. As Renee also once advised, “Buy the dress and figure out a place to wear it.” I have done so, from Las Vegas to Atlantic City to New York City to Melbourne, and places in between.

Recently, my GG friend Ms. Dee-ism described my dressing style, as “Bold. Chic. Edgy.” A dress I found at a New York City thrift fits that bill. It was a dress unlike I had ever bought–or worn–before. Short in the front, long in the back, and a bare back. 

I also knew that if I didn’t like it, Michelle might. 

We got together on a recent Friday night to have a drink at a favorite local restaurant, Le Ono. We’ve been there a couple of times before, though not too recently, and know some of the bar staff (Michelle also knows the owners, and I’ve met both of them, a husband and wife team). Michelle is adventurous and usually tries one of their specialty drinks, and this dress was adventurous enough, so I stuck to my normal cocktail, a margarita.

We talked, had a snack, and as usual, Michelle knew someone there. I try to be relatively low key when that happens, because I’m never really sure how people are going to react to me, although I’ve never had a bad outcome. We stuck around for about an hour, and then headed back to Michelle’s house so I could drop her off and drive home.

Once we got to her house, Michelle said she wanted to try on my dress (got that one right!). She put it on, and started dancing in her hallway, twirling and posing for pictures. She donned a pair of golden boots with a fringe, ones I had recently received from a friend on our crossdressers forum. Because of personal circumstances, the friend needed to purge their stuff, and shipped some of her collection to me. The boots aren’t really my style, but I knew Michelle would love them, and she did. They went really well with the dress.

In addition, I had brought to her house my black jumpsuit, which she has worn before, and loves. Her oldest daughter was going to prom, and some parents, including Michelle, were invited. She wanted to wear the jumpsuit for the prom pictures before, and the prom beginning ceremonies. You can judge for yourself, but she looks great in it.

As to the ceremonies, her daughter was named the Monarch, the gender less successor to Prom King or Queen. As you might guess, Michelle was extremely surprised and proud. 

I decided afterwards that given she looks so great in my jumpsuit, that it ought to be her jumpsuit, so I gave it to her. I did state one condition; she has to go shopping with me for a replacement sometime down the road.

While she was trying on my dress, I asked to try on the dress she wore to her birthday dinner. She, of course, said sure, and then added she was planning to donate it to a local shop that supports a women’s shelter. She pulled it out of the collection pile, and I tried it on, and it fit. It’s mine now, and more motivation to chunk down a little more (I often say I fluctuate between chunky and extra chunky). 

Now Michelle has a new jumpsuit, I have a new dress (and need to find a place to wear it), and my new look is with Michelle, waiting for her to test drive it out somewhere. Once she has, I’m going to want it back, because it’s too fun not to wear out again.