How I ended up wearing ladies boots to work

[Rebecca Watson]

Why don't you tell her? Explain that you found a pair of boots that you enjoy wearing and how comfortable they are and then just ask what she would think about buying another pair before they are discontinued? If you have photo capabilities on your cell phone, take a picture of them while wearing a pair of your work pants. She may or may not recognize them as a feminine style but at least you will be upfront and honest with her. What is the worst thing she could say? If the answer is no, then you are exactly where you are now and if she says that it is okay, then you have a green light to decide whether to purchase another pair. You will just regret not asking; avoid the regret and ask. Wouldn't you do the same thing if the two of you were out shopping and you found something that you wanted to buy? Good luck!

If I tell her immediately, most likely she'll insist that I throw the ones I've got away, along with all my other female clothes. That being said, I'm not actively keeping this from her. If she asks, I'll tell her the truth, but I'm not going to shove it down her throat. (She's probably already deduced that I'd do something like this, anyway.) For work reasons, my wife and I are in separate countries, so the only chance she'll notice is when we're on Skype.

Ideally, I'd like to open this up to further discussion with her at the opportune moment. My current plan is dressing in a way she thinks is fashionable (I'm quite familiar with her taste in clothes), making some effort getting it "right" and convincing, and, if I look reasonable and respectable enough, sending her a few pics and asking, "so, what do you think?". Who knows, though? If I'm unable to make myself presentable as a female, perhaps I wouldn't want to play dress ups as often anyway.

- Becky

[Geraldine_Whyman]

Unfortunately, nobody has yet said "Hey, are you wearing girls' shoes?"

- Becky

Hi Becky,

thank you for this story. I'd like to add that I've had the same kind of experience with women sandals at work... No react.

[BLUE ORCHID]

Hi Becky, They pretty much look gender neutral.

[lyndancgal3]

I have a pair of femme, slouch cowgirl boots and no one ever notices the difference