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.

(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.

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Just a guy who loves wearing women's fashions. My Genderbread Person diagram got me thinking about how I would describe myself…. I.E.A.S. …. Identity, Expression, Attraction, Sex. I identify as a man with a strong affinity for felling like a woman sometimes. I usually like to express masculine, and sometimes feminine. I’m male, and happy that way. I’m attracted to women.

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

Lady—thank you—You are serious right? I Would be allowed to go to work Dressed?

paula oden
paula oden
5 years ago

I too had some what of a retard boss just because i wore my panties at work he made fun of me and thought i was gay and so did some of my co-workers doesn’t matter what a person wears or their sexual prevferance as long as they can do the work i worked in a manufacturing plant and and when i bent over imprint of underware showed thru.

Active Member
4 years ago
Reply to  paula oden

Paula, Your boss is VERY fortunate that you did not decide to sue his sorry ass!
Good on you, for keeping it together, girl!

leah ward
5 years ago

I am now a full time female, I also remembered days looking at my GF clothes wishing I could wear them to my place of work. When I came out at my work place some people looked at me as some kind of freek but as time went on now I am one of the girls and love wearing my pencil skirts and heels to work

5 years ago

Well after reading the comments above I feel extremly lucky,After the big earthquake we had back in 2011 the building I worked in totally collapsed, now up until that time I had been just underdressing just the usual panties, cami’s stockings or pantihose after all the dust had settled I decided that the drab me could leave forever and Diane came out of the closet and has stayed out, I have been dressing female completely found a job where I can be me but unfortunatly I still have to wear a uniform but at least it’s a skirt, blouse, and… Read more »

Active Member
5 years ago

I was going to work in full on girl mode for nearly a year. One day the boss told me “you have to start dressing like a man”. I said “WHY??!!” He said “Because I’m the boss, & what I say goes!” Then he asked me “if I was wearing a bra & panties under my clothes?”. To which I shouted “That’s none of your F*cking business!!!” (I was, & still do!). If he doesn’t like it, I’ll let the lawyers battle it out in court! Imagine that man, asking me about my underwear???!!! UNDER WHAT CIRCUMSTANCES, IS IT OK… Read more »

Marie-Christine Bouvier

I really love to watch nicely dressed secretaries and I would love to go to work in a nice satin blouse and a skirted suit but that´s not possible. So I still dream about that opportunity and sometimes I wear my feminine lingerie and stockings or a panty hose under my male clothes. In winter time I often wear a ladies leather pants (jeans style) at work and my colleagues are ok with that (I guess they don´t see that the zipper is on the wrong side). Too bad that I cannot wear my nice pussy bow blouses, heels and… Read more »

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