On Halloween, 2018, I dressed as my then-girlfriend (now-wife) and she dressed as me.

The results were, as expected, hilarious.

First of all, she looks way better as me than I as her.

Which led me to do something like this…

And while I will spend much of this essay complaining, I have to admit that I did not wear heels, did not do full makeup, and did not shave that Halloween.

The latter was agreed upon by both of us. The one-night costume wasn’t worth a week of looking at me without a beard. “I’m just going to not look at you for a few days”, was the general vibe in our house the last time I shaved completely. It was not undeserved.

But even by half-ass dressing as a woman for 8 hours, and even with all the laughs and compliments we got that night, I still learned a lot more than I expected to.

Women certainly don’t need me to stand up for them, nor do I intend to explain the difficulties a woman in the world faces on a daily basis that I do not have to deal with as a man, a White one at that.

But I was truly surprised at how much I learned, how vulnerable I felt, and the reactions of people to my appearance while I was dressed something-like-a-woman in the Midwest.

What I Thought I Knew

My wife takes awhile to get ready.

Before dressing up as her, I understood what this meant from my perspective: I wait for her to get ready. More specifically, I wait a long time for her to get ready and when she says she’ll be ready in 5 minutes, I then begin my 15-minute process of getting ready to go. This is a habit of mine that she really, really enjoys.

Another aspect of my wife’s life that I understood only in the way that it affected me, was that it always took her longer to shop than me. I know this because I sit down exhausted on the couch outside Macy’s at about the 2 hour mark of our mall trip, a point in our outing that she would probably call, “half time”.

I’m a real Simone de Beauvoir of gender observation, I know.

But I only bring up these cliche observations to illustrate the surface level “before”, to be now followed by the slightly deeper understanding “after”.

A Brief Aside for Taste

To Jayme’s credit, she is a very discerning shopper and get-readier.

She has really good taste – from interior decor, to fashion, to architecture – and luckily some of it’s rubbed off on me.

The first rule of having good taste is both its biggest drawbacks and one of its greatest strengths: you simply do not buy something you don’t love.

Before my 30s, shopping for me was simple problem solving.

1. I’m going to Marshall’s right now (always Marshall’s)
2. I will find 1 item of the thing I’m looking for
3. I will purchase that thing

Shopping for a shirt? I will buy a shirt that I like enough because my goal is just to solve the problem of “shirt”.

Developing good taste means you do not settle for what you like enough. You learn what it is you love and you hold everything to that standard.

Back to the lecture at hand

But besides the good taste aspect, there is a fundamental difference in shopping for women’s clothes vs. shopping for men’s and it was not the difference I expected.

What I Learned

1. Women have a lot more options…except they don’t

I’ve always been slightly jealous of the options women have when it comes to clothes, especially in the workplace. A woman in an office setting can wear like 20 different things considered “acceptable” and most if not all of their options look much more comfortable than the male standard of dress pant + dress shirt.

Stretchy pants, white shirt and long sweater thingy? Sign me up.

Now, I’m a big girl. Finding clothes that fit was the first challenge.

But what quickly became dizzying was the 1 million possible combinations of textures, colors, and quite frankly, shapes that women’s clothes take.

To the latter point: it’s harder to tell the exact shape of a lot of women’s clothes until you try them on.

Folding women’s clothes as I do now that I live with a woman, I often encounter them out of context. And women’s clothes not-on-a-woman are confusing.

Like, if you don’t see this dress on a woman, what would you say is the actual shape of this piece of clothing?

My guess would be large pillow cover.

(Pillow covers with buttons are another a thing I’ve learned about from my wife. See also, pillow covers.)

What proved just as daunting as the 8 hours I spent as a very poorly dressed woman out in the world, was having to consider how these many shapes and textures fit my body.

It may appear that women have more options than men when it comes to clothing, but so many of those options are made for only small sub-sections of women.

And I often didn’t know they weren’t for me until I tried them on and then had to look at myself in the unflattering clothes under the unflattering lights of a department store changing room.

Which leads to point number 2 which could just as easily be 1b…

2) You have to actually think about, and constantly judge, your body-type while shopping for women’s clothing

Not only was shopping for women’s clothes a gymnastic mental exercise of matching textures and styles, but get this guys, women actually have to think about how the clothes their buying work with their body type.

On that one day of shopping I thought about my body, and it’s particular shape, more than I ever have at any time in my entire life as a straight man.

My goal while dressing like my now-wife was mostly to look funny, and I was still nervous. God forbid I had actually tried to look good.

As a guy, our biggest considerations when shopping boil down to, “is it too baggy or too tight?”.

Maybe the shoulders on our collared shirt are weird. Maybe it pulls too tight on our belly, or too loose. Maybe the sleeves are long. As far as tops go, that’s about the extent of our considerations. And plenty of guys aren’t even taken those minimal considerations into account.

What I quickly learned while having to shop “as a woman” was that there are infinitely more options, and many of them won’t work for the kind of woman you are.

Men’s body is cut into 4 parts: torso, arms, legs, feet. These are solved for with: shirt, longer shirt, pants, shoes.

Women have so many more angles to consider. Their clothes bend and blur the lines of their bodies in way men’s clothes rarely have in a historically Western context (a context which this entire essay – like its writer – exists within).

Do you want to emphasize your waist or your hips?

While you’re emphasizing those hips, do you want to hide your belly?

Are you showing off your neckline or trying to de-emphasize your shoulders? Both?

Do sun dresses make you look stocky instead of summery?

You might like the pattern on that blouse but too bad, it’s made for women with a tiny, tiny waist and no upper back.

As a man, if I see pants on a model, I can more or less expect there is a size of those pants available to purchase that will fit me. Sometimes I prove too husky for my fashion ambitions, but clothes shopping as a straight White man has not been much more complicated than seeing a thing, finding it in my size, and buying it.

Sure I wish I had more options, but I absolutely empathize with the constant objectification of one’s own body that one is forced to do while shopping for women’s clothing, and can only imagine what it must be like to have to do that from an early age, without the tools a smart, handsome, 34-year-old rapper-turned-essayist has for dealing with blows to their confidence.

And if I thought the shopping was rough…

3) Putting stuff on your face is terrible

I don’t like things in my eyes. 

And apparently, women have to use the sharpest, pokiest objects in their lives, right around their eyes. Everyday.

I did it once and they do it everyday.

I’m sure you get more used to pokey-stabby things in your eye sockets, but I don’t even consider wearing contacts because I don’t want to get used to putting glass circles in my eyes. (I refused to research what contacts were made of for this essay and also what shape they are.)

I thought women’s clothes had an overwhelming amount of options? Makeup is exponentially more complicated.

As the old, old saying goes: makeup is the clothes of the face.

It’s not just color and texture, it’s what do you emphasize and what do you diminish about your face?

You thought clothes shopping made you think about your body in ways you didn’t like? Get ready to think about your fucking face.

I can tell you right now the only way I’ve considered my face as a man was my decision to grow a beard 8 years ago. Beyond maintenance, I haven’t had to think about my face much since then. “And it shows!”, my wife yells in the distance as a drummer, in a distance further still, rimshots softly.

Honestly, as a low-self esteem, probably-should’ve-been-medicated teen I thought my face was pretty shitty in high school.

But as long as I didn’t look in the mirror in the morning I could avoid thinking about my face for most of the day. 

And thank god my school had those mirrors you only find in hood and hood-adjacent public buildings where it’s not a mirror but just a kind-of-shiny piece of metal with a bunch of scratches on it.

Women have to start thinking about all the “problems” with their face in their pre-teens and there is no worse time to think about your face than your pre-teens.

4) People look at you

Even after all the shopping and eye-stabbing, I still wasn’t prepared for the effects my wife’s clothing would have on my body until I went out into public dressed like her.

Now, I was a guy dressed as a girl, which means I will attract a certain amount of WTF attention in the Midwest, but it didn’t help my social anxiety that the clothes I was wearing were more revealing of my body than anything I’d ever worn.

Women’s clothes are inviting. Men’s clothes are literally closed off. 

Women’s clothes have openings where no openings should be, and then, no openings where openings should be (looking at you pocketless pants).

Women’s clothes have soft, flowing curves; they have varying layers of density, folds you don’t expect. Some of their shirts don’t have a back on them. Like, they make you pay for a full shirt when there’s only half a shirt!

Men wear button up shirts that cover our entire torso. And when that isn’t enough, we put a suit coat on over our shirt and close up the one space of vulnerability – our neck – with a giant rope tied in a knot (also known as a tie).

Dressed as my wife I went to my friend’s house, a house full of people in on “the joke”, who were all dressed up for Halloween, and I still felt uncomfortable.

We went to a tap house in a smallish town 90-minutes outside of Minneapolis (a small town large enough to have a tap house, that is) and the amount of double takes and long glances were enough to make me not want to walk up to the bar to get the drinks that would ease my concern with the amount of double takes and long glances I was receiving.

The vulnerability, the openness of my clothing and body, and having people look at you when you’re in that state, is something I never experienced to such an extent as a straight man.

5) Now, let’s break down how terribly I dressed as a woman.

1. What I wore:
   1. Crop top
   2. Jean jacket
   3. Palazzo pants
   4. Eyeliner
   5. Earrings (clip-on, and they fucking hurt)
   6. A purse
   7. A wig

2. What my chicken-shit-ass did not wear
   1. Heels
   2. Bra
   3. Women’s Underwear
   4. Lipstick

Basically, all the hardest stuff were things I didn’t do and I still had this experience.

So Long Tootsie!

This is not an essay to tell women what’s hard about their lives, but to tell men how little we really know about what they go through.

Dressing up as a woman for just a few hours taught me about my own physical vulnerability, and all the ways society gives me to cover it up.

I’m not saying that I didn’t expect leers for dressing as a woman. I’m not that naive.

“Omg guys have you heard about this thing where men hate women and also hate men who act even slightly like women?”

But you can expect it all you want.

Until you’re in that bar in that crop top and eyeliner, with a flowy bottom number that really opens you up to the world, you just can’t feel that vulnerability and insecurity.

I think I’m a fairly empathetic man. I consider myself a feminist and I consider feminism as the evolution of the human race that could save us as a species.

But just dressing as my wife for less than a day made me so much more aware – awareness that lived on my skin – about one small aspect of women’s lives. And I didn’t even start to experience the harder parts of womanhood than deciding what to wear.

What it’s like to have to worry about men everywhere you go? Will they hit on me annoyingly? Will the ask me to smile? Will they hurt me? Why do I always have to be on guard?

I have considered these questions before, as those of us who have done the work to sit beside women and listen to them have.

As men we should consider these questions, and we should listen to and respect the opinions women have about their own experiences, but judging by how much I learned just by wearing women’s clothes, I can now see my considerations of these safety concerns for the shallow thought-experiments that they were.