I Tried… Actually Caring About My Outfit for 40 Days

WSN’s Features Desk is running a new series we’re calling “I Tried…” Each piece will feature a member of our staff who’s added something new, weird or a little crazy to their lives. In this installment, Features Editor Kendall Levison starts dressing up every day.

I am not, by any stretch of the imagination, a fashionable person.

It’s safe to say that I’ve never been one. As a kid, my favorite outfit consisted of zip-off hiking pants and a bright orange muscle tee. Paired with a pretty terrible haircut, I was hardly an elementary school fashionista.

Evidence of my childhood fashion woes
                                 An example of my childhood fashion sense

Since I also went to schools that required uniforms, I never felt the need to develop a signature style that would distinguish me from other kids on the playground. I’ve learned enough to give up the cargo pants, but I’m still pretty clueless.

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In general, I’m okay with being a fashion Luddite. I feel like I know the basics — I can dress myself without embarrassing my friends and family, and that’s all that matters, right?

But “dressing like a grown-up” has always been somewhere on my to-do-someday list, right behind “learn guitar” and “living in a house with a secret room.”

I had the perfect opportunity to change my style earlier this year, when my two roommates and I decided to turn the tradition of giving something up for Lent into a bet.

All three of us had to write down our resolutions, and if anyone broke their promise they’d be responsible for cleaning our bathroom once a week until our lease ends in August (that’s about 20 potential cleanings for those of you counting at home). As for me, I decided to tackle my style head-on and dress like a “real” adult for 40 days.

Our written agreement, complete with signature
                    Our written agreement, complete with signature

My roommate, who interns at a well-known fashion house and is generally the best dressed person I know, helped me come up the rules for my project, since “dressing better” is pretty vague. After some tense negotiation, here’s what we settled on.

Every single day until Easter, I had to:

  1. Compose an outfit. Since my usual thought process while getting dressed is “Well, this is clean and vaguely seasonally appropriate,” this was going to be a challenge.
  2. Put on makeup. I’m never going to make it as a YouTube beauty blogger, but I can manage foundation, eyeshadow, etc. when I need to. We agreed that I would do at least the basics every morning.
  3. Do “something” with my hair. My hair is naturally what I like to call a “Hermione Granger in the first Harry Potter movie” level of curly, so I typically just throw it up in bun. That means that anything more complicated counts as doing my hair.
  4. Take a mirror selfie. This had two purposes — first, it made me more aware of what I looked like before I ran out the door. I also sent the photo to my roommates to prove that I was following the rules.

My roommate also went through my wardrobe, and pulled out a stack of clothes that I was not allowed to wear to class during Lent. This included my extensive collection of men’s flannel shirts, nerdy tees and, most heartbreaking of all, my yoga pants. But I gamely pushed them to the back of my closet and prepared to get my adult on.

      Sweatpants and flannel — two thing I gave up

Unsurprisingly, the first couple of mornings were rough. If nothing else, this challenge gave me a huge appreciation for people who are always well put together. You are magical creatures who I will never understand, and I salute you.

My first attempt a mirror selfie
                 My first attempt a mirror selfie

But I persevered. I did have a rotation of nice outfits in my head, although I felt a little odd wearing them to my 8 a.m. web design class instead of at dinner with friends.

My hair actually ended up being pretty easy as well. Although I’m not a fan of straightening my mess of curls, it didn’t take as long as I thought it would in the morning. I also invested in some clips, so I could wear my hair up and still look polished.

The area where I learned the most was probably makeup. I’m sure that most people already know this, but practice really does make perfect when it comes to applying things like mascara and lipstick. Eventually I got so good at my usual makeup routine that I started adding new products. Don’t ask about the liquid eyeliner experiment though; I’m still working on it.

The biggest surprise of my new routine was that I found it more convenient than my previous routine. Since my “dressed up” had become my new everyday look, I didn’t have to stress when I had special events like an interview or fancy dinner. There was more than one day where I planned to go home and change, then looked down at my outfit and realized I looked just fine.

                One of my typical “post-Lent” outfits

When Easter rolled around, I did breathe a sigh of relief. I had done it! Not only was I safe from eternal bathroom-duty, but I also could wear yoga pants and my oldest T-shirt the next day.

For my first week back to dressing like I usually did, I took perverse joy in dressing like a slob and ignoring my makeup case. Though I’m not dressing up every day and I plan to never take another makeup selfie as long as I live, I am paying more attention to my clothes and how they make me feel.

While I’m probably never going to be a trendsetter, I do enjoy looking good. My experiment made me realize that dressing up isn’t that hard and I can do it without spending too much extra time or effort. Who knows — maybe one day I’ll even master liquid eyeliner.

Email Kendall Levison at [email protected]

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