February Fashion Challenge, Days 18-19: Sk8er Boi and the Multiverse of Madness

Here’s something about working with high schoolers that I never expected; I find myself constantly thinking back to the people I wanted to be as a teenager, and wondering how all of those alternate selves could have turned out. What if 13-year-old Mo had told his parents that instead of moving to Seoul, he wanted to stay alone in Los Angeles after all? What if 15-year-old Mo had followed his gut and gone with Spanish instead of Chinese class? And what if 17-year-old Mo had managed to save up enough money for those skateboarding lessons he had always daydreamed about? Would those Mos have been more confident, more intelligent, more self-assured? Would they have been happy with who they were?

When I think about my students, I want them to live their lives without regret. I love imagining the different possibilities that exist for them – not just in terms of the schools they’ll attend or careers they’ll pursue, but the interests they’ll deepen, relationships they’ll develop, and values they will grow into. As teachers, counselors, and mentors, we play just one part in their lives, but in the limited spaces we share with them, we do our best to cultivate space for them to safely explore, experiment (and fail), and grow. I’m now in my fifth year of working with teenagers, and it’s been unbelievably rewarding to see my first class of 10th graders slowly grow into amazing adults in their own right. I hope the same for every student I work with.

But my students have also helped me realize that it’s not too late for me as well! For many years after high school, I felt like my time was up: I had spent all my formative years grinding away at the library, and now I would never be cool ever again. But that’s ridiculous. I’m only 27! There is still so much time for me to do all of the things that I might not have been ready for at 17, even when I’m 37 or 57 or 77. If I’m pushing my students to step out of their comfort zone and try new things, even (especially) if they fail, shouldn’t I be doing the same?

That theme – staying young at heart, keeping that hunger for adventure alive – is what captures the spirit of this weekend’s outfits. Saturday’s outfit is all about Gen Z fashion: bold colors, deliberate mismatches, and an unapologetically omnivorous attitude because if the world as we know it is ending, we might as well look good for it. Just as my kids push me to be more myself each day, I pushed myself to wear things I’d normally shy away from: Spongebob Vans, red shades, and pink chinos. My partner thankfully talked me into going with the chinos, despite my protests, and I’m glad he did because wow, I look great in those.

One of my former students rated this an 8/10 – quite generous, honestly. Thanks, dude!

Sunday’s outfit, meanwhile, hearkens back to my teenage skateboarding aspirations: it probably says something about me that this aesthetic actually isn’t too far off from what I wear in the classroom now. It isn’t too hard to pull off, either, as long as you’ve got classic jeans, a bold graphic tee, and a comfy flannel to tie everything together! I love the approachable confidence professional skaters carry themselves with: that sense that no matter how casually they’re dressed, they’re not to be fucked with. You don’t need to compromise your comfort to hold authority – an important lesson to convey to our students as they learn to navigate and transform the world they will inhabit one day.

Helmet and knee pads not included.

Here’s what I’ll say for now – as much fun as it is to speculate about the millions of other Mos out there, I’m pretty happy being the Mo in this universe. The one with a lovely network of friends and a fulfilling, demanding job and an apartment that he gets to call his own. The one who gets to do silly things like having his friends and co-workers and students dress him for an entire month, then blogging about it on the Internet. And who knows, maybe he’ll learn to skateboard some time soon.

Steal the look(s):

Saturday:

  • Red shades (Available at a Zenni.com store near you!)
  • Orange short-sleeve with hood and custom patches (I went through a short-lived phase during shelter-in-place where I put patches on EVERYTHING, from t-shirts to jackets. This hoodie was one product of that phase: it promptly went back into my closet and never saw the light of day. Until now.)
  • Old Navy merino wool long-sleeve T-shirt, white (One of the better Old Navy basics, and especially good if you’re doing any kind of workout in chilly weather.)
  • J. Crew 484 Slim-Fit Stretch Chino Pants, pink
  • Spongebob Vans (Another one of my students texted me to let me know they’ve got literally this exact same pair of Vans – I’ve never felt cooler in my life.)

Sunday:

  • Light brown beanie (Gotta keep the head warm while you’re doing your Ollies and 720s and whatever it is kids do on skateboards!)
  • Vans flannel, green/white (This doesn’t even feel like it was part of an outfit challenge because I’ve worn this SO many times to work/dates/school. A real classic, this one.)
  • Black NASA graphic tee (T.J. Maxx for the win!)
  • DKNY slim-fit jeans (Gotta admit, these are growing on me. Especially considering I only paid $15 for ’em!)
  • Black/rainbow Vans (These shoes just emanated gay energy – I had no choice but to get them!)

Coming tomorrow: Do these pants look too tight on me?

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