Yeah, But What Am I Supposed to Wear

I’ve only been posting every other week this summer.  I’ve been preaching a lot and I’m headed to the TEDSummit in a couple of weeks.  Those two things have gotten most of my attention. At the TEDSummit I’m doing a short talk and leading a discussion for the speaker’s pre-summit on the 21st, then Jonathan and I are leading a discussion for the full summit later in the week. Plus, oh yeah, I have to write another speech for a women’s event in Manhattan on July 18, right before I leave for Edinburgh.  I’m feeling good about the speeches.  I’m not feeling so good about what I am going to wear.

It feels like I’ve been here before, like maybe right before TEDWomen last fall.  Then I tried the personal shopper at Nordstrom’s and a couple of expensive boutiques for tall women, but ended up with stuff I ordered from Amazon.  I never order clothes from Amazon.

Half of the clothes I own are from Stitch Fix.  The speech I’ll be doing in NYC will be delivered right after the CEO of Stitch Fix delivers her keynote.  So there’s that.  And then I leave for Edinburgh, where the high is going to be about 62 degrees each day.  I don’t think sleeveless tops are gonna work in Edinburgh.

You know, there are people who say we choose to be transgender, because it’s so much easier than life as a man.  Uh, sure, right, yeah.  I can tell you what I’d be wearing if I were still a guy.  I’d be wearing jeans, khakis, a blue sport coat, and a few button-down collar shirts.  That’s all I’d be taking to New York and Edinburgh.  But no.  Life is not that simple anymore.

Everything I own is tailored for life in laid back Colorado.  Semi-formal here means a sleeveless summer dress and sandals. Every time I go to New York City, I feel like most women on the streets are thinking, “Honey, you can’t wear that here, or anywhere east of the Hudson River.”

I am extremely fortunate I can buy clothes online from major retailers.  To be honest, there is something wrong with that, because that means those retailers are making clothes that fit the frame of a 6’1” person with no hips, waste or curves.  In other words, they are making clothes for tall thin men.  I can buy 10-tall jeans from just about anybody and they’ll fit perfectly.  I don’t tell women that.  They get angry.

I did wear size 10-tall Old Navy jeans and an Old Navy sweater for my first TED talk, the one that’s been viewed over two million times.  The people who comment on YouTube can be cruel, but nobody criticizes those clothes.  They cost me about 45 dollars total, including tax and shipping.

I do wear expensive Tieks shoes because most women’s shoes are designed to be worn by manikins, not humans.  So when you find something that works, you stick with it.  I have lots of pairs of Tieks.  I mean, lots.  Women come up to me in the airport and say, “So, how many pairs do you have?”  It’s like a confessional for Tieks wearers. When I tell them how many pairs I have, I can always tell they feel better.  They go home and tell their partners, “You think I’m bad!  I met a woman with xx pairs of Tieks.” (Nope, I’m not telling you how many pairs I actually have.)

I am surprised at my style.  Before I transitioned, I had an idea about how I might dress.  I don’t dress that way.  I dress comfortably and if I could, I’d live in workout leggings.  But as my friend Kristie says, “Leggings are not pants.”

But back to the people who think we actually choose to be transgender.  Yeah, right.  You’re going to choose to switch to a metabolism that causes you to eat one potato chip and gain three pounds.  You’re going to choose to add 15 minutes to your morning routine just to do your makeup, you know, the stuff that cost you a thousand dollars at Sephora.  And don’t even get me started on skin products and the price of a haircut.

I’ll probably end up speaking to the CEO of Stitch Fix in jeans I got from Old Navy, and to all of those swells at the TEDSummit in an outfit I buy at the last minute from Amazon. This female stuff is not easy.

8 thoughts on “Yeah, But What Am I Supposed to Wear

  1. Welcome to the club! Tell me about it! I did not choose to be a woman, I “won” the 50/50 lottery 😩 I have fought clothing since before I can remember, since the first conflicts with my mother that she has described, well, after I woke her up every night until I was in first grade, were over clothing. Apparently I demanded to choose my own clothing at the age of three and she gave in, and my mom took hell from everybody including my perfect grandmother and aunt over what I wore. I resented how easy it was for boys and later men, why did they get it so easy, and WHY was Jesus a MAN like THEM?? In high school the only casual clothes that fit on top (according to my mom) were men’s t-shirts with raglan sleeves so they wouldn’t show how much too big they were to fit my square oversized frame. Now, not sure what has happened to clothing or my body, but nothing in women’s fits, I can’t get out the door in a dress because of what has to show below the hem, and men’s shorts, pants, and even men’s SHOES and sandals fit better than women’s. Even if I start dressing an hour early for something important, even just church if I can’t hide in my choir robe, I end up late and miserable in my sixth or seventh outfit since nothing else worked. Yes, I know you didn’t choose to be transgender, and I know you were a different kind of miserable before, but I understand at least in part what you are going through where clothing is concerned! AND I know from what I can see and read, you are now your true self 💕 but, still, in many ways, being a woman sucks!!! 😃

    Sent from my iPhone



  2. Good Morning. It brought a smile to my face. When you travelled out of ISP with that little briefcase you had your change of clothes in it. Never a suitcase. You had your navy blazer jeans and a button down and your loafers. Boy things changed.


  3. I’m a little bit frustrated that this very special and touching blog ends up asking what clothes are the right ones. Are these really the questions that we have to answer nowadays?


  4. Good afternoon; earlier in the year you were a keynote speaker at my university. I’ve had a lingering question that I was unsure how to properly phrase. I ask this in earnest with a desire to learn. You said that since your transition, you have faced hardships and discrimination in your workplace; that you attribute to being a woman. Do you believe that this is attributed to your transition or an issue woman everywhere face?
    Thank you for listening,


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