Dressing for work (or yet another reason why it must be hard to be a woman) 5

Someone at work recently posted a link to an article about the difficulties women face in choosing what to wear for work/interviews (great article, well worth a read – http://www.xojane.com/issues/professional-dress-for-women)

On the days where I present as male at work, so little thought goes into my appearance – I just grab a t-shirt and a hoodie, check to make sure my jeans are still wearable (SNIFF TEST), and then head into work. However, on the days where I present as female, every little thing becomes an enormous battle – I have to (fairly exhaustively) mentally prepare the night before, judging what outfits might and might not make me seem unprofessional. It’s not only the idea of what is or is not appropriate for work, but what you will be judged on for your choices.


How short is too short?

If I’m wearing a skirt or a dress, I have to consider length. If I choose a skirt that hits mid-thigh, since my legs are longer does that mean I’m technically showing more leg than a shorter woman wearing a skirt that also hits mid-thigh? What do the tights I’m wearing say about me? If they’re patterned, does it make it seem like I want people to pay attention to my legs?

There have been numerous occasions in the morning where I’ve put on patterned tights, decided that it draws attention to my legs, and then opted for my usual plain ones, or in some cases, opted to just wear jeans instead.

How high is too high?

I tend to wear heels when I dress up, because, well, I love heels. But there’s still the issue of which heels to wear. Are lower/chunkier heels more dowdy? Do they give the impression I’m less fun? Do higher/skinnier heels indicate that I’m slutty or looking for attention?

What does this dress mean?

Is it too low-cut? I don’t even have cleavage to show! If my dress is too tight, does that give the impression that I want to show off my body? If it’s too loose, does it imply that I don’t care about my appearance? If it’s too bright, does that say I want attention? If it’s dull, does that signal I’m a dull person?

How is my face?

What does this lipstick say? Is it too bold? Maybe I should try for something more muted? Is my contouring too severe? Should I tone down the eyeliner and rein in my wings? Is this too much blush? (Although if you have to ask, you’ve gone too far!)

Leaving aside the fact that I’m a crossdresser, just getting to a point in the morning where I feel like I look nice is a battle where I’m fighting off a universe of imagined judgements of what my outfit possibly says about me as a person.

Women have to go through this every day.

Read more about my thoughts and adventures on Being Out.

Leave a comment

Your email address will not be published. Required fields are marked *

5 thoughts on “Dressing for work (or yet another reason why it must be hard to be a woman)

  • Betty

    Dear Liz,
    That’s a very noce outfit to go to work with. By the way you look great in it. Moreover, you could also wear woman trousers to work, maybe a suite, with high heels.

    • Liz Summers Post author

      Thanks :)
      It’s a nice outfit, for sure – but like every day I go to work dressed up, it’s a struggle to come up with something!

  • Salina

    i love the yellow skirt and the polka-dot stockings!
    like you, i enjoy wearing heels. i used to be a little self-conscious about it, since i’m already a smidge over six feet, but i’ve seen cis women my height, so i just go with it.


    • Liz Summers Post author

      :D thanks Salina!

      Yeah, same as you, I used to feel a bit weird sticking out so much because I’m tall… but I figure if I stick out so much for other reasons anyway, why not just go with it! :)