Ashley Tries To Dress How Her 16-year-old Self Thought 30-year-olds Dress

I’ve been 30 for a couple of months now, and I highly approve.  30 is pretty nice.  Teenage years fill up with a torturous amount of FEELINGS and the twenties tend toward pressure and hard decisions and confusion.  But at 30, you’re expected to have some of your life figured out, I guess.

The theme for this week came from getting dressed in all black separates for a choir concert last week.  As I put on black trousers and a black shirt and black shoes and lots of black eyeliner, it reminded me of high school, because I did all black a whole lot more when I was around 16 or 17.  And when I had my look all together I looked at myself in the mirror and thought, “Wow.  This is what I was going for in high school, but I didn’t know how to do it.  This is what I was TRYING to achieve.”  It’s kind of a nice thought.  That made me laugh, but it also made think about my teenage aspirations.  At 16, what did I assume about my life at 30?

I’m kind of weird in this aspect, but I don’t tend to dwell on the past or do much planning for the future.  A lot of people talk about living in the present, but that’s my default.  I live in the future and I have a bad memory and pretty terrible planning skills.  I don’t do much comparison at all, which is why the idea of taking stock of where I am and measuring that against my teenage ideals seemed like an interesting experiment.

Here’s that black on black on black on black outfit.  The main reason I don’t usually do all black separates is that most blacks do not match each other and unless you go for black separates with radically different textures, the ensemble can be off-putting.  The other reason is that I love color.  But in high school, I hadn’t realized either of those things yet.  I wore black because I wanted everybody to see that I was serious and very into fashion and super mature and mysterious and DESERVING OF RESPECT AND ADORATION.  I was also going through an extended Audrey Hepburn phase and Audrey wore all black, so I had to wear all black.

At 16, I was sure that future me would be a serious fashion designer (with emphasis on the serious part).  If I had watched The Devil Wears Prada at the point, I would have related to Miranda Priestly, which is NOT the preferred takeaway from that movie.  Looking back, I would have told little me to talk to more people, to be less serious, and to loosen up.  I was a little too good at being mysterious.  At my graduation, probably less than ten people in my class actually knew me as a person.  My “mysterious” persona was just a way to avoid opening up to people, so I wish I had pushed myself to talk more.

16-year-old Ashley would have really liked this all black outfit, but she would be shocked at how tight my jeans are and she would be disappointed that I was a data analyst and not a fashion designer or at least a costume designer.

I was trying to remember one of my favorite outfits from high school…. then I remembered and immediately started laughing.  I’ll talk you through the elements:

  • Nondescript baggy jeans.  I didn’t know jeans were supposed to fit at that point.  I didn’t anticipate skinny jeans in my future.  Or in ANYBODY’S future, for that matter.
  • A bright white canvas jacket that I called my “Luke Skywalker Jacket”, because it had those square military-style pockets on the front.
  • A neon orange, oversized, long-sleeved t-shirt that I found in the boys section of a Gap Kids store.  Since the neon orange probably wasn’t garish enough to make sure that people could see me from space, it also had GAP in giant reflective letters across the chest.
  • Some sort of shoes.  Maybe clogs.  Maybe bulky tennis shoes.  Maybe Birkenstocks.  Don’t remember much about my shoes at that point.  I have a bad memory and that can be a mercy.

I can look back on that crazy outfit with fondness, because I really loved it.  Nobody else would have worn it.  I was brave to the point of foolhardy.

In an homage to my neon t-shirt, I wore my brightest neon jacket.  It’s so orange that everybody feels free to comment on it.  People have said that I look like a convict, like I’m going hunting, or that I fly an x-wing.  X-wing pilot is my personal favorite.  It’s a bold look, but Fortune Favors The Bold.  It’s hard to be as bold as a teenager who doesn’t know anything, because the more you build, the harder it is to risk.  Nobody cared what I wore when I was 16.  Nobody cares that much now, but it feels more important.  I just need to go for it.  Be bold and happy.

My style references during high school were all from old movies.  Those movies shaped me.  My style icons were Audrey Hepburn and Lauren Bacall and Natalie Wood and Katharine Hepburn.  I didn’t have any current pop culture knowledge at that point (current here being early-2000s), so I think it’s pretty adorable that 16-year-old me was absolutely convinced that that a fashion design career was not only likely, but inevitable.  While it’s good to have some fashion history, knowing what’s going on currently is kind of important for a fashion designer.

I think it’s pretty fascinating how influential Audrey Hepburn was and continues to be.  I don’t think she was necessarily the best fashion role model for me, because I not only went through an all black separates stage, I went through a boatneck top stage.  Boatneck tops look wonderful on Audrey Hepburn.  They make me look top-heavy and matronly.  At that point, the fact that Audrey and I have VERY different body types didn’t even occur to me.

When I do throwback styles now, I don’t go for Audrey.  I go for Lauren Bacall or Katharine Hepburn or Rosalind Russell, because their style was more based around their personality and not around a specific clothing style.  I want to own my style, rather than having the style own me.

I think 16-year-old Ashley would be confused if I went back and told her what I’m doing now.  The plan was to grow up to be a cool, fierce, respected, serious fashion designer.  A woman who has everything together.  A woman who could give anyone a run for their money.  A woman who always stands out, but stands apart.

I’m not that superwoman.  I’m a 30-year-old data analyst who spends a lot of time working with spreadsheets.  I live alone.  I’m definitely not serious, because serious people don’t laugh so hard that their noses run.  I think I’m hilarious, even when I’m not.  I’m a total nerd.  There is so much stuff I’m bad at.  If I need to do something that is out of my comfort zone, I freak out.

But even though I grew up to be a happy nerd, I still found myself breaking into the fashion world through a side door.  I’ve been making Polyvore boards for a few years now and my boards have been viewed over 400,000 times!  I have Polyvore contacts and followers all over the globe, including a small (but dedicated) band of followers from Bosnia.  Who would have guessed?

The fashion game has changed and I’m in it.  In a small way, but I’m still still in it.  Living the dream!

The point is this –  life doesn’t go according to our plans, but that’s not a reason for disappointment.  In high school, I mainly thought about myself, because I didn’t have a job, I didn’t have to support myself or my family.  It was easy to be self-absorbed.  My plans were as small as my vision and my vision was as small as myself.  Thank goodness we don’t have to write our own stories.  We’d leave out all the good parts.  I didn’t know that I’d go through times that left me in tears and drove me to my knees. I didn’t know that I’d cry at good news.  My world has gotten so much bigger since then, but my world is still small.  Imagine how much more I’ll learn in the next 30 years.

Here are a few things I took away from this week:

  • I thank the Lord I am no longer in high school.
  • I have gotten less serious as I’ve gotten older.
  • Talking to people is hard, but it is great.  It’s true that people are sometimes the worst, but people can also be the best.  So be brave and get to know more people. (That’s the one piece of advice I wish I could have given to myself during high school.)
  • Comparisons can be odious, especially when you compare between What You Wished For and What Actually Has Happened.  Remember that only one of them is real.  Give thanks for the real one.
  • When expectations meet reality, give yourself a break.  The things we wished for can hurt us if we let them.  I thought I’d be married by now / I thought I would have a house by now / I thought my career would be steady by now / I though my fashion creations would be on the cover of Vogue by nowI thought I would have lost that weight by now.  Give thanks for what you have NOW.  And work from there.  Make a plan and work on it.  But don’t give your expectations the same weight as reality.
  • Keep learning.  Don’t let yourself stay in the same place forever.  Keep developing your mind and your soul.  Our desires should change as we grow up.  Be honest with yourself and surround yourself with honest friends who love you.
  • I know I’ve said this before, but the hardest times of our life are also the times where we grow the most.  We would never plan on the trials, but we need them.  Without them, our vision would stay small forever.
  • I’m not where I imagined that I’d be by now, but I’m so glad.  I’m grateful for where I am at right now.

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