I’m out visiting extended family for the holidays, some of whom I have not seen in two years, and all of whom I have not seen since my latest shortest haircut.  Even in my early 30’s I somehow feel somewhat teen-like, visiting family with a new haircut and a nose ring, with clothes a little bit butcher than they might remember.

Family members certainly have a way of mixing compliment with critique, with a (kind?) “Your hair is so beautiful, you should grow it out.”  I used to have long flowing wavy red hair, the kind that made others jealous sometimes apparently.  It was the kind of hair that attracted all sorts of straight males and garnered lots of compliments from women who coveted long hair or frequently dyed their hair to find the perfect color.  It’s true, as a red head I am lucky to have color while others are greying, etc., but regardless of what I have that other folks might wish they had, I deserve to present how I like and feel attractive doing so!  I rely on the (real!) compliments of my friends who are awesome and tell me hot how I am, rather than telling me I would be beautiful if….

While it has taken some time to gradually shift my wardrobe in a direction that feels more appropriate to my gender identity and presentation, I have been feeling more confident a lot more frequently, in the town in which I live, and even at the office.  My heels are high up on some shelf in my closet, and my skirts hang off to the side unworn.  I rotate through a handful of slacks and button down shirts, and have developed more of a collection of knit boxer briefs and socks to go with my Fleuvogs.  Dressed casually I feel the most confident, both probably because it feels like the shifts in my casual wear are less extreme, and I am more comfortable in casual wear in the first place.  I like jeans, converse, thermals, and hoodies.

I stressed a bit packing for this visit to family, both because I would be traveling to a different climate, and because I started thinking about how I might feel more uncomfortable around family than I do in the rest of my life.  I think that part of this stems from facing individuals who may expect that I look the same as when they saw me last.  As far as I can recall, I think that it is quite likely that I look different every few years anyway.  My style has changed quite a bit over the years, from a scruffy but feminine hippie, to a messy art student in baggy men’s clothes, to a more refined woman in fitted jeans and tighter shirts, and gradually settling into a butcher more masculine but still somewhat genderqueer dress as of late.

With all that said, I shaved my armpits but not my legs, packed tank tops with built in bras as undershirts, and all my favorite knit boxers and boxer briefs.  I also packed jeans (men’s and women’s), some long sleeve jerseys to wear under concert tees and some short and long sleeve button down shirts.  I topped all of this off with some mens’ hoodies and a suit jacket.

I walked in the door to my cousin’s house on Christmas day in men’s jeans, a casual short sleeve button down shirt, and my short boyish hair.  I was greeted with hugs and some strange looks.  My 80 year old uncle blurted out “I didn’t recognize you!” as he gave me a hug.  I think his comment made me feel stranger than anything.  I don’t intend to confuse my elderly relatives.

Honestly, I think so far the reaction to my transitioning appearance has been quite uneventful.  I think I am much more concerned about my appearance than anybody else.  My insecurity vamps up in apprehension of a reaction or a judgement.  And it keeps me from doing things like walking around in my boxers.