Skirts and Heels for Work

[Gige]

To all...

I am looking for some solid advice about wearing skirts and heels to the office. In case you have not read my previous posts, I offer this recap... I recently started wearing heels to work (3"- 3.5" max) or flat knee high boots with skinny jeans. Overall, I have not had any problems in doing so if one excludes the usually unwanted advice "You should wear this that way or you should wear that this way" from the peanut gallery of Statler and Waldorf (see my post "The Ladies at the Office" for more details on them).  Nonetheless, I am wanting to move into wearing appropriate skirts with very professional style heels or boots into the office but do not know if I am quite ready to do so. I have told many of those in my office about my genderfluidity and let them know that if the future how I express myself may be different than what they have observed in the past. No one seems to care all too much, which is fine as I do not want my clothing choices to cause a disruption of the day. Details of the photo - an outfit for a "work at home day." Boots are Tulip (model) from Jessica Simpson. I would love to wear this outfit to the office someday...

So, any advice or thoughts on this are welcome.

[Tech]

Please keep this on-topic and NOT make it about gender, otherwise it will be closed and removed.

[Cali]

Wear the high heel boots to work first.

[Jkrenzer]

This is a nice look. I agree with Cali though. Stick with the heels minus the skirt for a while at work. Eventually once your coworkers become used to it, don a skirt. I like these boots and as fellow heel at work member go ahead and wear your higher heels if and when you desire. As for myself I'm in 5 inch stilettos most every day. It's been great, but there were initial questions etc.

[Bubba136]

I agree.  I would wear the shirt and boots at first and wear the skirt and the rest of the outfit after your coworkers get used to seeing you dressed that way. Your ear rings and nails polished, along with a nice necklace and other accessories should set the mood for the skirt. 

Edited April 2 by Bubba136

[Gige]

11 hours ago, Jkrenzer said:

This is a nice look. I agree with Cali though. Stick with the heels minus the skirt for a while at work. Eventually once your coworkers become used to it, don a skirt. I like these boots and as fellow heel at work member go ahead and wear your higher heels if and when you desire. As for myself I'm in 5 inch stilettos most every day. It's been great, but there were initial questions etc.

Thanks! As I like to say, it never goes out of style to have style!  Nonetheless, thanks for advice as it is solid in terms of practicality.   

[Gige]

9 hours ago, Bubba136 said:

I agree.  I would wear the shirt and boots at first and wear the skirt and the rest of the outfit after your coworkers get used to seeing you dressed that way. Your ear rings and nails polished, along with a nice necklace and other accessories should set the mood for the skirt. 

I've got the nails polished and necklaces, but the earrings are still posts as they were done in late December. I was told six months before taking them out overnight and a full year before hoops (which stinks!). I hope to "graduate" to small hoops at the end of the six months as they are much more to my liking and would help with a transition to skirts.