I dressed like a guy for five days

I decided to test social norms and dress up like a boy for five days. Normally, I’m the girl who loves a pretty dress with my face and hair done perfectly – letting loose for five days was very strange.

Every day I wore baggy man clothes with no makeup. I kept my hair either under a hat or in a low bun, and really committed to looking the part.

To give it some perspective, here’s an example of a normal work day outfit, or the type of thing I’d wear if I was going out:

Going boyish was very much out of my comfort zone. Here’s what happened:

Day One: The working man

I work at a wealth management firm where the dress code is ‘business casual’. I decided to keep it simple and wear a button down with jeans.  Business on top, casual on the bottom – close enough to business casual.

It was strange wearing pants that weren’t fitted for me. My colleagues definitely gave me some weird stares… very, ‘What the heck are you wearing?’

I felt like I went unnoticed and people only interacted with me when needed. Apparently the girl dressed up like a boy scared them away. 

Day Two: The casual Dad

I wore a baggy shirt, pants and a cap when I was going to a friend’s place.

After a few stares, I eventually explained to them what I was trying to accomplish. They all thought it was crazy, but very interesting. I could slowly feel myself relaxing into my new persona – I not only dressed like a guy, but I tried to sit like one and act like one. I started cursing more and acting more rash. Everyone definitely started to notice.

I think the best part was embracing the careless attitude most guys have.

Day Three: The loveable thug 

I went out Saturday night to a local bar dressed like a “thug.” I wore shorts and a sweatshirt with the hood up. On a normal night out, I’d go out with my girlfriends and we’d all get hit on. But this time, I was by myself and no one even bothered to say hi.

It was interesting to see how my appearance changed the way people treated me. I usually make a ton of new friends in bars, and this time I did not get that vibe.

Day Four: The college athlete

Today I headed to the gym – not in my usual sports bra and leggings. I stuck to running on the treadmill, but loudly grunting while I lifted mad weights may have been more fitting for the aesthetic I was rocking.

No one really cared when I was there – I definitely wasn’t the weirdest looking person and you can get away with looking pretty awful when you’re exercising.

Plus, working out in a typical guys’ attire was much more relaxing – far less constriction. 

Day Five: The frat boy in training 

For the last day, I dressed like a typical frat boy, and it was my favorite outfit from the five-day experiment. I wore a plaid shirt, white shorts resembling Chubbies and a cap. It just so happened I needed to take a trip to CVS and buy new makeup, so I went into the store and asked an employee where they kept Revlon makeup.

The employee looked me up and down and then pointed towards the makeup. The same reaction came from the cashier, but I just kept smiling and ignoring their stares. I think that was my favorite interaction, because the employees I interacted with were so startled as to why this girl in boy’s clothing would want to wear makeup.

Overall, this social experiment made me really appreciate being a girl. It comes with its own set of problems, but I would much rather wear a dress and makeup than any outfit a guy would ever wear.

Even though boy clothes are more comfortable, I enjoy wearing a pretty dress and dolling myself up with makeup. It is almost like a shield against the world, while as a guy, I felt more vulnerable. I learned about how appearances really change the way people treat you, whether they are your friends or strangers.

Moral of the story: People will judge you based on your appearance, and basketball shorts are very comfortable.