As a guy, I’m lucky to have one of those jobs where I don’t have to wear a uniform.  We have a loose dress code,which means casual clothes are fine most of the time.

Yet, each workday, I get up, walk into my closet, and stare at lots of guy clothes that I just dread wearing to work most days.  Instead, my mind wanders over to my collection of dresses, feminine jeans, cute tops, and the neatly stacked boxes of heels, flats, wedges, and a small collection of purses.

I reluctantly get dressed for work, only to find myself always carrying an extra pair of shoes, often flats, complimenting the rest of my guy outfit, for some unexpected chance to wear them.  Often, this pair of shoes is the excuse I need to stop my car, swap out my guys shoes for them, and wander around shopping for an hour or two in some store or another.  A quick stop at one store results in stops at several stores.  Eventually, I get to work and walk sadly into my office wearing my guy shoes, wishing I could have just kept my feminine shoes on for the rest of the day.

For months, this daily ritual was the same.  My mind would begin to tire at the confusion and battle of wills.

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Then one day, a realization.  My work does have a uniform in that men are expected to dress a specific, professional way. This has brought some comfort and finally resolved the daily mind battle.

My female coworkers have no idea how much I admire their cute blouses and coordinated skirts, skinny jeans paired with conforming heels, colorful tops matched to flats, and fashionable purses accenting jewelry.  They might complain about how hard it is to get ready for work each day, but they at least have so many exciting choices of what to wear without needing to calculate the risk the way I do.  They do have other challenges at work with equality that I’m so glad I don’t have to deal with.

To fit in, to keep the stress a little lower, to fund my CD wardrobe, I wear the uniform while fantasizing that I’m wearing something more feminine.  For some unknown reason, maybe a future hope, my thrift shopping usually focuses on putting together outfits that define the real me.  Even if I could or had the confidence to dress feminine every day, I think I would end up facing new closet challenges.

(1) Finding enough decent fitting styles that are also appropriate for work would take some time.  I’ve realized that longer tops look better on my body shape.  Revealing tops with low cut fronts or no sleeves probably need a sweater or scarf over to fit in with other women at work, who always seem to wear layers at the office.  Jeans and pants are safe, skirt and dress hemlines need some extra thought.

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(2) Shoes.  Stilettos are attractive, fun, sexy, and all the wonderful adjectives.  They’re okay for a day or two in the office, but definitely not practical.  Flats are extremely practical, can be cheap, and come in countless shades and cuts, making them versatile for many outfits from pants to skirts to dresses, and even shorts.  Wedges are a nice balance between the beauty of stilletos, and the comfort and stability of flats.  A pair of sneakers with pink or purple hightlighting would be good for luchtime walks, or just to give those calves and feet a break.

(3) Winter wear.  I recently bought my first women’s jacket after realizing one cold winter day that I needed one.  Hoodies are great for that really casual, or didn’t spend any time getting ready look.  I would prefer cute sweaters, lace or crochet, thinner ones that could be layered with tank tops under and jackets on top.

(4) Purses.  I love the look and feel of purses, from hand bags to crossbody purses.  The only issue, I really don’t like leaving my wallet, keys, and phone just sitting at my desk – maybe that’s because I’m used to carrying everything I need in my pants pockets.  I noticed one days that many of the ladies at work carry a purse, a lunch bag, a briefcase, and some carry a gym bag.  Four bags, I’m guessing 40 lbs in all, slung over both arms.  I have seen some really nice totes and large purses that can be both a purse and carry most briefcase items.  The other challenge with purses is being able to easily switch between them – that’s where investing in a nice wallet is worth the convenience.

(5) Accessories.  Yes, finding jewelry from necklaces and bracelets to go with all those outfits for work.  Fashionable women at work seem to never wear the same accessories more than a few times a year.  I don’t know how they keep track of all that jewelry, I have a hard time keeping a few bracelets and chains organized.  I’m not much into Fitbit, so I tend to wear a watch, which I realized lately that I needed a nice feminine one.

Ideally, I just want some social flexibility to pamper myself in womens outfits some days and blend feminine looks into my guys outfits most days.  It would be so mentally productive to get rid of this distracted feeling of wanting to wear what I feel like isn’t welcomed in the workplace.  In the meantime, I “dress” outside of work and wear the “uniform” to work.

EnFemme

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Simone
Simone
7 years ago

Lea, Wow, you really made me think. The place where I work is like yours– it has no written dress code but expects a degree of professionalism in dress. I have been pushing this for years. Dressing in feminine clothes always makes me feel comfortable and secure, like you I really hate guys clothes. Anyway, I always include some feminine piece(s) of clothing with my work outfit. of course, my bra and panties, Jeans, a blouse, my pink converse sneakers, my rings… Nothing too over the top, the key for me is to blend in, not stick out too much.… Read more »

skippy1965 Cynthia
Ambassador
Trusted Member
7 years ago

Great article Lea and so on point! I too long to have the choices women have and be able to let Cyn shine at work! i DO underdress every day (undies,trouser socks,camis (and in cooler seasons tights or leggings) and for last few months I have been wearing women’s slacks as well that could pass for regular men’s khakis. Have a few women’s polo shirts too!! Now all I need is a pair of women’s loafers that is a bit androgynous and`I can be dressed 100% female with no one but me knowing! One day I will hopefully be able… Read more »

skippy1965 Cynthia
Ambassador
Trusted Member
7 years ago
Reply to  Lea

We aren’t allowed to wear sneakers to work unfortunately though I DID wear my ladies sneakers to the amusement park last weekend and no one said anything! I am too close by other folks to wear perfume at work though!

Cyn

Joanna Lambeau
Joanna Lambeau
6 years ago

I too have been dressing full time in woman’s clothes. The only male clothes I have now are one pair of shoes and a vest. Everything else I own and wear is female and no one seems to notice. I have even started matching little dangly earrings to the color blouses I wear. I still wish I could wear dresses and skirts though. I have to wear a vest now to hide my breasts as I have been taking hormones on my own for over 12 years and now the last 2 years with an endocrinologist. I so wish I… Read more »

SteffieC
Duchess
Active Member
7 years ago

Oh to be able to dress as I want and not as I must. I have to wear suit and tie every day now. Have not had to do that for nearly 15 years. Still underdress as much as I can and dream of the fabulous flowing dress or the cute blouse and skirt.

JaneS
Member
JaneS
7 years ago

I spent a large part of my working life in a uniformed environment, wearing the male uniform whilst admiring and coveting the female uniforms. Sadly though, to my mind anyway, over the years the push for female equality (and I am very much for equality) has had the negative side effect that many uniforms are now unisex, some even no tailoring in differences for the male and female forms.

Oh well, these days I dress however I feel like pretty much every day.

Thank you for a great article.

Jennifergordon
Member
7 years ago

When I was working I always fantasize D about wearing dresses and skirts. Men’s clothes are ugly for sure. For now it’s panties and stockings!

Lynn
Lynn
7 years ago

This is interesting because what I have done is acquired ladies slacks and nice jeans and tops like oxford blouses and such along with penny loafers and ladies shoes that are somewhat “unisex" . I wear knee highs and ladies undergarments all the time , NEVER men’s undergarments. Very rarely will anyone say anything except maybe an older women. The younger people I work with don’t ever seem to notice or just don’t care. I have never had a male colleague say anything either no matter what his age. So I wear nice classic ladies clothing ALL the time even… Read more »

MacKenzie Alexandra
Duchess
Member
7 years ago

Your article really made examine my situation. My place of work also does not have a formal dress code aside from the contractual expectation that we dress professionally according to our job specifications. As man, that means trousers, a collared shirt, and my oxfords. These are few options as opposed to my female colleagues. I have often complained to my wife of the inequality between what is professional acceptable for my coworkers of different genders. Now, I do not want to forgo all of my male wardrobe in favor of my female wardrobe. I enjoy the option of dressing to… Read more »

Dani' class='avatar avatar-64 photo' height='64' width='64' />
Dani
7 years ago

I have worn women’s androgynous blouses, shirts, polo shirts, patterned pocket jeans, slip on shoes with 2″ heels, dress slacks, and underdressed for over 35 years daily to work and now that I am retired I still do so. As a manager at work none took notice of what I wore. My wife of 35 years never noticed. I always did the laundry so this was never an issue. I came out to her 10 years, she complete wardrobe is out of hiding and in the closet including my numerous pairs of shoes. She is not understanding but started to… Read more »

Marianne
Ambassador
Active Member
6 years ago

I could really connect with your feelings. I would also like to be able to dress as I wish for work. I have though gone a step further. I commute by bus for approximately one hour in total. A few times a week, I put on makeup, wig and female clothing and ride the bus as a woman, entering one stop before my usual one. At my destination, I either change in the station’s restroom or cover my female clothes with male trousers and a coat and change at work. This works well since the am usually first to come.… Read more »

Johnnie
Duchess
Member
6 years ago
Reply to  Marianne

I recently I began to go out in public as Lisbeth. When I go out in public I wear casual clothing such as blue jeans and t-shirts or a pretty dress and heels when I go out at night to watch a play or opera. I always avoid wearing over the top fashion that make me look like a drag queen. I am not a transvestite/crossdresser, I am a transgender girl. Even though I am passable because I am blessed with a feminine body, initially I only dressed in private. I became depressed about hiding myself and fully expressing who… Read more »

janedon' class='avatar avatar-64 photo' height='64' width='64' />
Member
janedon
6 years ago

If Only we could dress how we please all the time– working in the service industry, I have a little freedom of expression– I can get away with wearing womens cords (not bright colors) there are “Some" womens blouses I can wear—Last yr I got my ears pierced (a new guy at work came with pierced ears so I got mine done—mind you, I wear more feminine ear rings–Not the nice dangly ones but like today–Studs with pink stones (I just tell everyone they were gifts) -My breasts are still small (B cup) & some guys at work notice but… Read more »

Dame Veronica Graunwolf
Active Member
Reply to  janedon

Hi Jane. How about Security Job with Securitas. They have plenty female guards and are Canadas largest Security Company. Chief to contact is Christine Morton at Ontario H/O in Toronto. Unionized company and pay little better than minimum wage and plenty OT. I worked for them for 3 years in downtown Toronto building watching for fire panel alarms……that is why I am on diet now.
Best of times to you….Happy New Year!

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