Monday, January 3, 2022

Michael Scott: Crossdresser

I was a regular viewer of The Office during its original run (2005–2013). And I have been a regular viewer of Comedy Central’s reruns of The Office.

The Office does not offer much trans-wise. In the 2005 “Halloween” episode, Michael Scott (Steve Carell) mentioned that he came to work two Halloweens in a row dressed as Monica Lewinsky.

In a 2007 episode (“The Negotiation”), Michael mistakenly purchases a woman’s pantsuit from a bargain bin and wears the suit to work. Michael took some ribbing because of his fashion faux pas and that was the end of it... or so I thought. 

A few days ago, I was watching a rerun of a 2010 episode (“Nepotism”) that I had seen a few times in the past and for the first time, I noticed the following exchange between Michael and the office receptionist Erin Hannon (Ellie Kemper) when they discover an outgoing package that had been shipped.  

Erin: Oh my gosh – those are the pants you wanted to return to Talbots.

Michael: I'm reconsidering sending them back anyway. 

Erin. I'm sorry. Do you want to try them on again just to see...

Michael interrupted: I know they fit. It’s not about the fit.

Evidently, in this case, Michael intentionally shopped at Talbots, a specialty retailer of women’s clothing, shoes and fashion accessories. Go figure.


Source: Rue La La
Wearing BGL

Jocelyn
Jocelyn shopped, dined and took a short walk in the park. Of the thousands of people she saw in the city that day, she was the only person in a dress or a skirt.

20 comments:

  1. OH
    ---CRINGE---!!!
    I liked Jocelyn's photo and pose.
    What really caused me a CRINGE, was her wearing those stilettos and
    having to navigate that irregular cobblestone walk!
    It takes a 'real pro' to navigate such a course and not twist an ankle- or two.
    Since COVID, my ankles and navigation skills have become weak...
    Recall the lady in the Advil commercial?
    Velma

    ReplyDelete
    Replies
    1. Velma,
      I am certainly “no pro” walking in heels. The shoes I wore that day were only 3” heels.
      I do admit that I did catch a heel once in a crack that day, but only a mild miss-step.
      I really do love wearing a skirt, no matter what others may think.
      Jocelyn

      Delete
    2. Jocelyn, I made the comment as the heels height appear higher than 3".
      As for skirts, and 'showing some leg'-- you did a great job and your legs made a great impression in the photo.
      Hey, if one is going to 'do THIS thang' then show some leg, and some HAPPY!
      One of my greatest adventures was visiting the local ULTA cosmetics store in a bright spring-style sun dress. My shoes were open toed pumps, so I was quite steady in my stride.
      The ladies in the store loved my style, ect...
      Spring is only about 82 days away....
      Velma

      Delete
    3. Velma,
      Your kind words about my looks are very flattering, thank you so much.

      The 3” heels are as high as I want to go. With them I am 5’ 19” tall. I know Stana supports tall women, but I am way too noticeable; skirt or jeans.
      Jocelyn

      Delete
  2. presumably due to feminist fashionistas, it seems the vast majority of bio women (especially younger ones) now seem to think it is naff to wear a skirt or dress for everyday activities such as shopping - instead, only considering that diminishing option from their wardrobe in the following circumstances:

    1 - for hot sunny weather
    2 - for power dressing at the office
    3 - for going out on the town

    this was happening before the virus came along of course, but i think its arrival has pushed at least another couple of nails in that particular coffin. options 2 and in particular 3 above have been hard-hit for the last couple of years as a result of its presence, and who wants to go to the trouble of choosing to put on some heels, hosiery, a dress and make up in order to feel nice and feminine... only have to stick an hideous-looking mask over their face?

    ReplyDelete
    Replies
    1. Gina,
      I couldn’t agree more with you. Mask wearing certainly discourages going out and trying to look “lady like”.
      Jocelyn

      Delete
  3. I don't think Jocelyne's experience is so unusual these days, it seems to me that unless there is a dress code being imposed most people just seem to live in jeans and sneakers. I personally think this is a great shame, dressing properly makes me feel good, there are few men who don't look better in a tailored suit, and few women who don't feel special wearing hose and heels. Last year a few of us tried to introduce dress up Friday in opposition to the dress down Friday idea, since working at home most people were dressing down all the time!

    ReplyDelete
    Replies
    1. Paula,
      Dress up Friday sounds like a great idea. But alas I’m retired.

      I really love wearing a skirt, so when I do go out, which is rare, I will show my legs. Maybe a revised fashion will emerge when others see what I am doing.

      Jocelyn

      Delete
    2. Leslie LangfordJanuary 03, 2022

      There was a time before the advent of television that the BBC required all of its radio announcers and news presenters to wear a suit and tie even though they were unseen by their audience. The rationale behind that was that doing so would put them into a more "professional" frame of mind, and that this would reflect accordingly on the quality of their work. Can't argue with that logic, and I am sure that it would still apply today despite the stampede towards casual (read: "sloppy") workwear nowadays.

      Delete
    3. Rachel McNeillJanuary 05, 2022

      As my male-self, I still wear nicely tailored trousers, cotton dress shirts, and sweaters or fleece pullovers with dress shoes much of the time. I think sweat-pants and old t-shirts shout "I retired and stopped caring about myself." I know that puts me seriously out-of-step with the times, but I am vain, whether presenting as Brian or as Rachel.

      Delete
  4. Stana,
    Thank you for showing my picture. I feel privileged to be seen on your site.

    Even though I was the only one wearing a skirt that day, I felt wonderful and completely comfortable being the woman that I am. I’m sure some of the people who saw me must of thought I looked nice.
    Jocelyn

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  5. "...The Office does not offer much trans-wise."

    Perhaps it was a bit too early to pick up on certain topics?

    I'm not sure how much influence Ricky Gervais had on the American version. I do know he was heavily criticised by UK standups following a series of trans related jokes. In the Netflix series, Afterlife, Gervais's character is more sympathetic in the given situation, so where does he stand?

    https://www.pinknews.co.uk/2021/01/05/james-acaster-ricky-gervais-transphobic-stand-up-video-cis-boy/

    ReplyDelete
  6. Come to an event like The Keystone Conference. I'll hazard the guess you'll see more people in skirts and dresses than you'll see for the rest of the year!

    ReplyDelete
  7. The ladies pantsuit brand MISSterious! LOL. I saw that episode recently, it was cute. No back pockets on the pants. "They are Italian!"

    I have actually wanted to find a nice pair of ladies slacks that I can wear while in guy mode for stealth crossdressing. They would need to have the right kind of styling to no be too feminine though on first glance.

    In my youth I used to have fantasies where I would go to work where the office dress code was wearing skirt suits for women AND men. =)

    ReplyDelete
    Replies
    1. i like the term "stealth crossdressing"! thanks to women more-or-less dressing as men most of the time these days, i have had that idea myself for the last few months now as a means of "if you can't beat 'em, join 'em". i started off with some black trainer-type shoes and black cotton briefs, the latter of which i wear all the time now. but earlier this week i needed to go out and both my geezer t-shirts were in the wash. so i threw on a plain black but silky ladies top from my transvetic wardrobe instead. i always wear foundation garments whilst dressing so it felt i bit snug around my midriff, but other than that i soon got used to it whilst out walking. of course being the middle of winter it was hidden under a man's fleece and jumper, but as the weather happened to be exceptionally mild for the time of year i later took the jumper off and pulled the fleece zip down a few inches - thus exposing my ladies top to the world at large ha ha

      like many i have been laying low of late when it comes to shopping thanks to the virus, but as and when it finally clears off i am planning to go into the city centre and replace all my casual mufti clothes (which are practically rags now) with similar stuff from the ladies fashion racks of department stores!

      Delete
    2. When I got out I will "stealth crossdress" because I am not at the phase of doing wigs and makeup, but it is comforting to blend in wearing ladies jeans or shorts and some basic button down blouses. Men will never notice. Women are observant and may notice but I don't care. I am with the sisterhood!

      Delete
  8. Rachel McNeillJanuary 05, 2022

    I don't get as much Rachel-time as I would like, but that's all on me. I'm 100% out and have a fully supportive spouse.

    Funny thing, I purchased some stretchy, colored jeans for Rachel, and wear them pretty regularly as my male self. I'm a runner and workout regularly and have maintained my shape into my 60s. That pretty much opened up things. I now wear a little of this or a little of that, irrespective of which closet it comes out of. Whatever looks good on me.

    As one genetic woman acquaintance of mine said "Show the best; cover the rest."

    ReplyDelete
  9. What a lovely picture of Jocelyn - she looks absolutely wonderful. Had similar experience in Perth, Scotland in the summer when wearing a colourful summer dress, although I did opt for flat shoes.

    ReplyDelete
    Replies
    1. Julie,
      What an absolutely wonderful comment you have made about me. Your kindness has made me so happy, and it makes me feel beautiful. Thank you.
      Like you it doesn’t bother me to be the only one walking around showing some leg. Do that makes me feel so feminine.
      Happy New Year to you.
      Jocelyn

      Delete
  10. How could you not mention the episode "Women's Appreciation", where in the mall Michael mentions the topic of role-play. If you read between the lines, you can figure out that Jen is cross-dressing Michael into a school-girl during their sessions. (Maybe into something else as well. And they do tapes!!!)


    Michael: What do you think of role-play?
    ...
    Michael: Well, Jan has this schoolgirl fantasy.
    ...
    Michael: I just, I feel uncomfortable wearing the dress
    (The look Pam gives to the camera is unforgettable)

    It's also important to note that "The negotiation" episode was just 3 episode before, where Michael spills the bean TO JEN that he "accidentally cross-dressed". You can imagine based on the expression of her face that the cogs started turning, and she started to formulate a plan.

    ReplyDelete