Transitioning at work in three weeks

[Sara Olivia]

I will hit a big milestone in my transition in three weeks - beginning to work as Sara. Everyone has been told and the response has been supportive and positive. I am very excited. I work in an office environment where we all sit in front of our computers all day and do not really have to interact with any clients. For this reason the attire for everyone is very casual. The women typically wear jeans and sneakers, typically with a plain top or sweater. Rarely do any of the women wear make up aside from perhaps a little foundation. This puts me into a bit of an awkward position. On that specific day in three weeks time, all my colleagues will be expecting me to walk into the office as a woman. If I want to fit in with the other women though, I will pretty much look like a guy wearing a wig. When I go out in public I always wear some make up to try to hide my masculine features and look more feminine. I typically wear skirts to hide the lack of any hips. Clearly I do not want to show up to work dressed to the nines because that would clearly be inappropriate. What are your opinions in that matter? What would you do? Dress precisely as the other women do to fit in or go a bit beyond to actually try to present looking as much like a female as possible. I know some of you are very passable so could fit in under any situation, sadly I would be fooling myself if I thought I was one of those lucky ladies. Thank you so much for any input. I greatly appreciate it.
Sara

[Georgette_USA]

Sara

The avatar pics are too small for me to assess just how good looking you are.

As someone who also worked in IT, at first was mainframe maintenance than switched to PCs and Networks than just programming. I had to wear pants for work, not very ladylike to get on the floor or under in a dress or skirts. I continued that later in programming as seldom needed to move equipment around, but just got used to it. Because we still worked in open customer areas, could not wear jeans and sneakers much. As for makeup I never wore much but did use blush and lipstick and light eye shadow, otherwise my face is colorless. You did not say if your facial hair is all gone yet, Mine was gone by the time to work full time. Plus some light jewelry helps some.

I would think that if you follow their lead with just some little extras, doubt if people would look at you odd. Instead of sneakers maybe those little girly flats that many wear. Maybe some colorful or slightly fancy tops would work. I would wear some nice blouses and such, but got tired of them getting dirty. Who knows you might up the others in their presentation, women can be competitive in that.

Can't help with the wig thing, I was lucky to have my own hair with sufficient styling to hide my slight bald side crowns, but did have to put it in a pony tale for some work, as my hair did get long after a couple years in the back.

Not sure if we can post pics in here, or I would show my work ID after my name change.

I found an old post of my work ID.

https://www.crossdressers.com/forums/showthread.php?236842-Inspired-by-Judy-Somthing&p=3897962&highlight=georgette_usa#post3897962

[Mirya]

Congratulations on your upcoming milestone! That's very exciting!

As for what to wear? You wrote that when you go out in public you always wear makeup and typically wear skirts? Then I think you should totally wear that to work! It's what you have the most experience wearing, so you're most likely to feel comfortable and confident if you dress similarly. And that's what's most important - to be comfortable and confident in yourself as a woman on your first day, regardless of what you're wearing.

Oh, and I also think it'd be a great idea for you to bring treats for everyone to celebrate your first day. Bake some homemade cookies or better yet cupcakes for the office to enjoy. They'll love you for it! :)

[Persephone]

I love Mirya's idea of bringing treats, particularly homemade treats, that first day.

Your goal should be to fit in, to become "one of the girls," because the other women in the office will become your friends, your lunchmates, and your confidantes. You don't want to chance your reputation with them.

I would pick things very similar to what they wear, maybe jeans or casual pants, a nice top similar to theirs, maybe with a V-neck so you can wear a simple necklace, and maybe the pretty flats that Georgette suggested.

I would let my femininity be carried by curves (bras are wonderful things!), hair/wig, nice but casual jewelry (especially earrings [simple rather than dangly might be best], and no heavy, clunky bracelets), and lipstick/lipgloss.

Be friendly, cheerful, and, most important, smile. Smiles work miracles! And they relax you and diffuse tension.

Above all, enjoy yourself -- it is your day! You've just graduated and moved into the real world!

Hugs!
Persephone.

[Pat]

My experience to date is that the clothes you wear aren't especially important as long as you're within the norms for whatever you're doing. The most important thing you can wear is a sincere smile. Think how hard you've worked to get to this point -- you must be happy, right? Project that happiness. People read that. A few months after I started presenting full-time I started getting the same feedback from all corners -- "I love to see you come by -- you seem so happy." And you know what? I am happy. Even my worst day these days is a total win over the best day I had as a male impersonator. My advice is let people see your joy, if you have it. That will win them over. Don't fake it because that will drive them away. (As noted, yummy snacks won't hurt either. ;) )

[AlyssaJ]

My thoughts: On the wardrobe, I'd personally would just go with what fits in with what the other women wear. Lack of hips? Have you tried wearing juniors sizes (odd-sizes)? They are generally cut for women with a lack of hips and butt and can help accentuate what will be most flattering. However, more important than your clothes choices will be your confidence as a woman. If you're uncomfortable or self conscious in jeans, don't wear them. Maybe a more casual skirt or dress if that makes you more comfortable? Especially for your first impression, going in with confidence in your self and owning it is going to be critical. If they see you as unsure or shy, that can color people's opinions very quickly.

That leads me into the makeup conversation. Again you need to do whats comfortable. There are ways to wear enough makeup to look more feminine but not look like you're going out to a gala or something. Foundation as always, then very light and very subtle blush. Maybe just a little eye shadow but very light and close to your natural skin tone, and the most important thing, a light touch of eye liner. For most, eye liner alone can work such wonders. For me, to do a light job I just put some black on my lower water line (tear duct to outside corner for me works best) and a brown just above the lash line on the upper. Thin lines no smudging. Maybe that'd work for you. I'd try experimenting to find a natural look.

Good luck, I'm really glad you asked these questions. It's forced me to think about what I'm going to do the first time I go into the office after my November 1 transition date.

[Megan G]

My advice would be to go into work with the intentions of fitting in with the other women. If they typically wear jeans, sneakers and casual tops than I would be wearing the exact same thing! Being over dressed is just as bad as being under dressed IMHO... that first day is going to set the stage for you and a lot of opinions will be formed then....make it count.

As for make up don't overdo that either. A light foundation is ok to even out skin tone but by all means don't go all smokey eyed and heavy on the blush. You want a natural beauty look, not heavily made up. My suggestion is to start yourself on a serious anti-aging/pore minimizing Skincare routine such as Rodan & Fields. Make up gets old fast and it takes a while to undo years of neglect/sun damage and to remove wrinkles. That way in time your comfortable with no foundation/BB cream. It was one of the best decisions I made...

Good luck and enjoy it.. you only have 1 first day ☺️

[karenph]

Sara Nicole -- congratulations on your transition. a good luck on your first day!

[Heidi Stevens]

Go get 'em, Sara! You'll be fine, just be yourself and smile.

[AllieSF]

Yes, by all means "Go get them Sara!!" I am so happy for you. As others have said wear clothes to fit in and that you feel comfortable in, and that to me also includes skirts. One day you will look back and ask yourself why you were so worried about that first day at work.

[Sara Olivia]

Wow, thank you all for your great responses. I am very grateful for each and every one of them. Thank you Mirya for the wonderful idea of bringing treats. I will certainly plan to do that. All of you ladies have given me a lot to think about. The plan now is for me to go shopping for a work wardrobe next week. My wife has offered to help me also and of course I have accepted and am grateful for her input as well. I've not made a final decision yet as to which way I will go - dress to perfectly fit in with the other ladies in the office or dress in a way that I am most comfortable while still trying to dress in a fashion relatively similar to all the other women. What I will promise though is to let you all know how my first few days at the office went. As of right now everything is still on track for the first week of September.
thanks so much everyone
Sara

[Krisi]

If all the women dress a certain way and you want to fit in and be one of them, my suggestion is to dress like them as much as possible. Being a woman isn't all about makeup and high heels, it's mental.

You probably should try to cover any beard shadow and wear just a touch of lipstick though. You would be safe to "girl up" just a bit over what they wear but not enough to stand out.

[Sara Olivia]

Hi Krisi,
I agree completely with you that "being a woman isn't all about makeup and high heels" in fact I'd say that being a woman really has nothing to do whatsoever with make up and high heels. I really was not trying to come across in that way with my post - its not at all where I was trying to go. On my first day as a woman at work I would very much like to make a good first impression. I believe first impressions are important in shaping how people perceive you from then on forward. So while I do not want to overdress and show up at work like I would going to a dance, I also do not want to show up pretty much looking like my male self with a female hairdo. The question I posed, and I believe most people understood, was where to draw that fine line between overdressing or on the other hand looking very much like a guy wearing a wig. Neither scenario would leave a good first impression on my colleagues. So I am hoping to achieve a look whereby I still can look feminine yet not overdone for a casual office environment.
Yes beard shadow would have been critical 18 months ago but fortunately laser took care of everything but some white hairs which I'm still having removed by electrolysis. Still, I will definitely want to wear a bit of foundation, a touch of lipstick, eyeliner and perhaps even a bit of eyeshadow as Alyssa suggests.

[Krisi]

That's pretty much what I meant in my last sentence above. Best of luck to you.

[Megan G]

The question I posed, and I believe most people understood, was where to draw that fine line between overdressing or on the other hand looking very much like a guy wearing a wig.

This might be me misinterpreting a little and if it is I apologize in advance..... but is that how you think you look if your dressed down in jeans and sneakers? A guy wearing a wig? You also mentioned that you wear skirts most of the time to hide the lack of hips... just my opinion but I think your projecting insecurities onto other people. People are not going to think your a dude because you don't have hips... they are going to think that omg look at that persons slim figure... my advice is to spend more time dressed down to get more comfortable with that look prior to the start of transitioning at work. If you wear skirts all the time that is something that they WILL NOTICE and talk about.

Seeing your from Vancouver, my suggestion would be to go to your nearest Le Chateau, they have some really cute tops that can pair nicely with a pair of jeans and then wear a nice pair of flats...spend some time on the face and hair and you will be good to go (and shine) But at the end of the day you need to be comfortable as that is when your personality will really come out.

Forget about your insecurities and just go be you! this is your chance!

[Sara Olivia]

Hi Megan thanks for your advice. Yes you are correct that I still have some insecurities about my appearance. I suppose after a lifetime of seeing a male face in the mirror its difficult to now see a female face. I have been told by many people who know me and have seen me or my photo that they would not even recognize me if they came across me unknowingly. Most came across as sincere. I am leaning towards your suggestion about the jeans, top and definitely will be wearing flats as heels would definitely be out of place. And I agree that wearing skirts all the time is not an option, perhaps from time to time. But thank you for your input and you are right I will just have to learn to forget about any insecurities and finally live my life in the way that I've always wanted to live it.

[Mirya]

I can literally count on one hand the number of times I've worn a dress or a skirt since going full-time over a year ago. Even my cis female friends wear skirts more often than I do! lol. I usually wear jeans or denim shorts, but sometimes I will wear ankle pants too (don't like capri pants though).

Jeans are great, but I highly recommend staying away from skinny jeans. Skinny jeans are great for most cis women because most cis women have a pear body shape, and those jeans help reduce the appearance of their bottom section. But for most trans women, we have an inverted triangle body shape, and skinny jeans will make our legs look skinnier and therefore our upper body look bigger - exactly the opposite of what we want. Personally the only time I wear skinny jeans is in the winter, and even then only when they're tucked into a pair of riding boots or UGG boots. For trans women, a snug pair of bootcut jeans over a pair of sneakers or boots really helps give a better appearance. The flared leg draws attention away from the hips and gives an overall curved look. If it's too hot to wear bootcut jeans, you can wear straight leg jeans or even boyfriend jeans. The latter is a super relaxed fit (which can give the illusion of hips). Cuff them once or twice at the bottom for a cool but chic look.

A great casual alternative to jeans (especially in the warmer months) are cropped chino pants. You can buy them in a wide variety of colors. If you wear a brighter-colored cropped chino pant with a comparably darker top, it helps balance out your proportions, making your bottom look slightly bigger while making your top look slimmer. A very simple color combination is a white chino pant with a blue top. Or an olive green chino pant with a black top. You get the idea. It's an easy way to dress casually while also giving you a more feminine body shape.

That should get you started into the world of casual clothing. I recommend doing Google searches for "how to dress for inverted triangle body type". Read articles, watch videos, and take notes. Once you get a general idea and the basic rules for dressing for your body type, follow Pinterest for style and fashion inspiration. There are many, many ways to dress in a decidedly feminine way without wearing skirts or dresses.

Of course, learning all of this takes time and experimentation - luxuries that you don't necessarily have since your first day at work is just a few weeks away. So on your first day, just go with what you know and wear a skirt or whatever makes you feel comfortable and confident. But start now by learning more about fashion! Dressing as a woman is not about wearing skirts or dresses, but about knowing how to dress for your body type, knowing how and when to combine prints and solids, knowing the right colors and color combinations for your skin tone, and knowing how to accessorize with the right handbags and jewelry. If you dedicate yourself to learning these things (and there's such a wealth of fashion/style information on the web!), you'll learn it just as other women have done their whole lives. It's just that as trans women we have a lot of catching up to do. :)

[MarieTS]

I suggest fitting in, not standing out. You can still look feminine, just don't overdo it. Makeup is necessary, but keep it appropriate to your environment. And of course a wig is essential, but you should not wear an overly stylish hairpiece. Be the girl you would picture yourself being in that setting. You will do fine and hopefully in short time will receive validation and acceptance from some of the females in your office.
Good luck,Sara, your dream has come true ��

[Sara Olivia]

Mirya, thanks so much for taking so much time to provide such thoughtful and thorough input. Its really greatly appreciated by me and you should know I took a lot of your advice to heart. Didn't buy skinny jeans though that seemed to be mostly the type of jeans found in the stores. Marie thank you so much for your comments as well. I agree about making sure the hairstyle is not overdone. I am hoping to fit in with the other women in the office.

Anyways two more days in male mode at work then next week I begin working as Sara. Its becoming very real. IT is already in the process of deleting my email account and network id and access to be replaced with a new network ID and email address. I thought I might be a little sad to see my old persona disappearing but to be honest I do not feel that way. I can hardly wait to see my new email address and network id with Sara on it. I will not miss the old me. I will add to this thread next week once I begin working as Sara.

[Kaitlyn Michele]

Frankly showing up in dress and heels will make you more of a guy in a dress if you are not dressed for your office..

i think you are making a good decision to fit in...

and if you can do it with confidence and smile...let people know you are comfortable with life, they will respond..

nothing to see here, just doing my job....
and let them come to you..

im rooting for you!!! you are doing it

[Rachel Smith]

Myria that is one great post. Admin could we get this post in one of the sticky sections?

Now back to the OP. I too was nervous as mouse in an eagles nest on my first day. If you heed the advice here and keep your dress appropriate it will be a small deal. I dressed like the other women at the PO and still do. Nothing was said either way and no one has said a word to this day. Now it's just work, do your job as best you can and no one will care.

Just be yourself, breath and you will relax in no time. Your planed well and now you will see the benefits of that

Hugs
Rachel

[grace7777]

I started going full time in June, and am now facing issues that you will be facing. Personally, I like wearing dresses. Right now I am working a temporary job. Where I work some women wear slacks mostly and there are others mostly wearing a dress or a skirt. Because of this I feel I do not stand out by wearing dresses a lot. I do wear slacks once or twice a week. Now wearing pantyhose in the summer would make me stand out, and I have not yet wore pantyhose to work. I think you are pursuing a smart path by trying to dress to fit in. Wish you all the best.

[Kaitlyn Michele]

That sounds ALOT less casual!! i worked for years in corporate dress code environement....men wear suits, women do too....lots of dresses and skirt suits..

i rarely see women wearing pantyhose anymore

I cant imagine liking to wear it out...its like being a sausage!!!

[Sara Olivia]

Well I have completed my last day of work as a man today. Next week and forever after it will be as a woman. Since I work on a military base, in a civilian capacity, ID is a huge issue. All the paper work is signed by management and in place so that on Wednesday, my first day back at work my former male identity will cease to exist at work, replaced by my now female identity. I am ecstatic.

[AllieSF]

Sounds wonderful and maybe a great time for reflection and a look further into the future. Also a great moment to celebrate after your new first day of work. Enjoy.

[Persephone]

Awesome! Congratulations! May this be a wonderful first day of your life!
(And we will want to hear all about it!).

[Caroline Varg]

Wow - what a hugh feeling it must be. Congratulations! Of course we would like you to write a full story about it!

[kimdl93]

So many great and encouraging stories being shared here!!! Congratulations to each of you!

[Rianna Humble]

That's great Sara Nicole! Even though it was before time began, I still remember my first day on the job as the real me!

Must be time to :Party2: :Party: :rave:

[Sometimes Steffi]

It's probably too late for any advice, but you might want to go into work a little more girly for just the first day.

I have some very casual skirts that I might wear the first day, and then switch to jeans,

[Nicole Erin]

If everyone already knows you are going to start living and working as Sara, then why not just dress as you feel comfy? Maybe not like club attire but suppose you want to wear skirts, why not do so?
Someone said that people WILL notice and talk about it. Well they are going to be talking about you (at least until it is old news after a couple days) whether you wear frumpy jeans or a skirt. Maybe a knee length skirt since it is a work place.

If you are going to work with little or no makeup, jeans, and a boring top, what is even the point of so-called transition? So many TG want to live this full time but don't want to put much effort into their looks. Even if one doesn't pass, others will still take you more serious if you make an honest effort to look the part.

With shoes though, gauge those according to to how much you have to walk around (like if the break room and restroom are 500 miles away like where I work), if you are going up and down staircases, how much you are on your feet... If foot comfort isn't a big thing, go for some 2 or 3 inch basic pumps if dressing professionally.

Here is a good question for whoever -
Do you really think it helps a TG pass better if they are going around in jeans, no makeup, and basically looking like they did before trying to live a new gender role? Even if it does, then what is the point of transition if you are presenting basically the same? That whole "I am a woman in my mind" is a load of crud. You cannot just live as a woman in your head. You need to look, sound, and live the part.

I tell you where i am at - I live this full time. Given the work I do, skirts are not really an option (I climb ladders a lot) but nice top, slack-type shorts, makeup, hair, voice etc. No I do not pass that great but I do look good, I hear it often. You can too. Just don't be lazy with presentation and you too will hear often about "OH I love that (whatever)..."

[Krisi]

I think it helps a TG pass better if she dresses for the time and place (and that includes makeup). She will pass better if she is dressed like the women around her. The workplace for most women is not a fashion show. Look around. Letter carriers, delivery drivers, military personnel, retail workers (except for high end clothing or jewelry), factory workers. What are they wearing? Comfortable, appropriate clothing. Some will wear moderate makeup, some none at all.

I'll agree, a transsexual might benefit from some makeup to hide masculine features but the key is to just wear enough for that. Don't go to your post office job looking like you are going to a nightclub.

[Sara Olivia]

Hi Ladies,
Well, today was my first day working presenting as Sara. It was a wonderful experience. My colleagues and managers were all great and friendly and supportive and it was just awesome to be addressed by my female name. Everywhere from my email to my personal identification card is now in my female name and with my female photo. A great day at work though I will admit that I nevertheless felt stressed for much of it simply because this represented such a huge change. In a meeting today my manager referred to me several times addressing me as Sara and it took my brain a moment to register every time that he was referring to me. An unusual experience. As promised, here is a photo of how I was dressed for my first day of work. Hopefully it will meet with some approval from all the ladies here who have been so helpful to me with this thread.281762

[Becoming Brianna]

Congratulations Sara! I'm so happy for you!

[grace7777]

Sara, you look very nice. Happy to hear that things went well for you on your first day as a woman.

[Persephone]

Lovely! Congratulations and Best Wishes!

[kristinacd55]

Congrats! You look totally natural and at ease, nicely done. I have 2 close friends who transitioned at work (both truck drivers!) and both had for the most part a fairly easy time.

[Nigella]

... As promised, here is a photo of how I was dressed for my first day of work. Hopefully it will meet with some approval from all the ladies here who have been so helpful to me with this thread.

You do not need approval from anyone on this forum :D

[Pat]

You look awesome! Every bit like a woman I'd expect to meet in an office setting.


In a meeting today my manager referred to me several times addressing me as Sara and it took my brain a moment to register every time that he was referring to me. An unusual experience.

I was talking to my therapist about this just yesterday. I was telling her I had been at a gathering where everyone was using the right name and everyone was being careful to use appropriate pronouns and it was wonderful, I loved it, but it was still feeling "new." I asked how long it takes for it to become routine. She told me in her experience it really takes people three years to settle into the new identity. Her thesis is that normalcy comes after you've experienced things a number of times and some things (e.g. Thanksgiving dinner) only happen once a year. However, in your office environment, it should work itself in pretty quickly because you'll experience it daily. I don't mention this to make it sound like there's a long road ahead, but just to say forgive yourself if a year down the road you find yourself nervous as you approach one of those less-frequent experiences.

Congratulations!

[Krisi]

I'm glad it went well.

[Sara Olivia]

Hello Ladies,
My first week working as Sara is now in the history books and it was a wonderful experience for me. To think that this is how the remainder of my career will proceed has brightened my future immeasurably. I can now hardly wait for the day when I will never have to switch back into male mode. So here, in this thread I have worried for weeks about the first impression that I would leave, especially on the female staff, and many of you helped me greatly in deciding how I would present at work to achieve the first impression that I was hoping for. As coincidence would have it, for the first two days of work there was not another woman in the office just me and about a dozen guys. They of course could care less as to how I was dressed. It wasn't until yesterday, Friday, that one of the women finally made it to work. Nevertheless thanks to all of you I now have what I believe to be a totally acceptable work wardrobe consisting of jeans, capris, and other dress pants and matching tops. I will post the photo of my first day at work as promised and the past two days I was very comfortable in a pair of jeans and pretty top. As it was a bit cooler here yesterday I added a black sweater to the outfit. As expected, I felt very self conscious this week and nervous though that was mostly all self imposed. My colleagues were all very friendly, as they have always been, and very respectful. They all used my female name and the correct pronouns when referring to me and did their best to make me feel comfortable. A few times in meetings when someone addressed me using Sara, it took my brain a moment to click and to realize that it was me they were talking to. I am already a lot less nervous and stressed about the coming weeks and in fact am looking forward to it. I also have to say its an amazing feeling to now only exist as a female at my place of work, that is, with my female name on the sign in board email letter head and signature, computer networks,etc. I should have done this decades ago.

The only real challenge of the week came from a totally unexpected direction. I had bought this pair of ankle high tan colored suede boots that I thought looked really good with my jeans. In hindsight I should have worn socks with them that day. As it turned out by the end of the day I had massive open blisters on the backs of both of my feet. Rather than breaking in my new boots it was my feet that ended up losing the fight. So I am wondering, with the current forecast of rain ahead next week, what shoes I will be able to wear that will not cause agonizing pain to walk in. So that is all I am going to say for now. I will continue to add to this thread if and when I feel something interesting or helpful to others thinking of transitioning in the workplace occurs. I've loved all the feedback and useful advice that so many of you have already provided to me. I would love to continue to hear from you - I know many of you are far ahead of me in your transitions and have years of experience in the workplace as women. I am sure that you are treasure troves of advice and if you have any to offer I'd love to hear it. Thank you all for taking the time to reading this post and to Sandra and Nigella for hosting this very helpful website. I have learned so much from so many of you over the years and I am sure that is a significant contributor to why I am where I am today. Thank you all for the nice comments. I've never had a post on this site that had more than a handful of responses and was completely oblivious to the fact that there were a whole bunch of responses that I had not even seen yet. So sorry.

[Starling]

Just a thought here, Sara. As much as some unhappy folks yearn to return to the good ol' days when humiliating others for being different was winked at, I believe everyone--including would-be harassers themselves--benefits from workplace rules prohibiting it. This is certainly not to say that the men or women in your office would have behaved any differently in the absence of such rules; you are obviously well-liked and respected by your co-workers.

I think it's wonderful!

:) Lallie

[Aunt Kelly]

No need to apologize, Sara. On the contrary, you should be seeing all those posts for what they are, a celebration. Join the party!

[Richelle]

You look like any other women in an office setting. I can not wait until I am able to do the same

Richelle