UPDATED: I can NOT believe I forgot to post this picture! Yes, my pal Debi & I are goofing off, but we actually dressed like this for a trip to the mall. I wish I was kidding.
Awhile back a friend of mine posted a letter to her 16-year-old self. I have debated since then what I would write in a letter to my teenage self. Once I get past the advice on 'there's more to life than boys' and 'put a little more effort in at school', all that is left is fashion advice. And OH MY LANDS did I need it at times.
Dearest Teenage Gerb,
Hey there. It's me, 37 year-old Gerb, and I've got something to say, so I'm just going to say it. Some of your clothing choices scare me a little. Don't get me wrong, I still admire your love for finding unique thrift store items and wearing them proudly. But honestly, Gerb, some of your match-ups are frightening. I think it may have started with what you wore your first day of high school. We both know that was not your fault, that you were simply following the advice of someone you trusted, but those Levis should have been washed at least 20 times before you actually wore them in public... and that white t-shirt with the huge, puffy, green Gumby on it? It still makes me shudder.
I'm fairly certain that that was the day you decided not to care what anyone else thought about your clothes. It was easier to pretend you didn't care than to be visibly hurt by the pointing fingers and barely stifled giggles of the girls who enjoyed hurting others to somehow elevate their own self-esteem. This is when you were struck with the fact that you didn't seem to fit in anywhere. And so you came back with a vengeance, deciding to mock the cookie-cutter girls with your outlandishly unique looks.
As much as I admire you for dressing in one-of-a-kind styles, there are a few things that I would advise against ever wearing again. For example, long underwear knee-length cut-offs beneath short skirts just look kind of trashy. And cut-off shorts with thigh-high lace nylons are definitely not the right look for you. They portray the wrong message... and that message is not "I am unique".
Eventually you will tone down some and take your fashion in another direction. I'm not sure what to call the days when you would wear the clothes that the boys you were interested in were wearing, but again I need to say that this is really not you. Besides that - they are boy's clothes and you are a girl. Wearing the same brands as the surfer boys won't make them notice you. Being yourself will. Don't be afraid to be feminine. Remember that sort of psychadelic 60's dress you found at Goodwill, the one you pictured yourself wearing with lime green tights and your white suede slouch boots? The one you didn't buy because it wasn't baggy enough to hide your lack of shape? You are going to remember that dress for the rest of your life because you didn't buy it. That dress was unique, tasteful and feminine. It was a perfect expression of YOU.
I also remember a dress that you did buy, another that you will always remember. It's a hideous, white, sleeveless thing, all covered in frilly lace. You will buy it because of peer pressure and at FULL price. I know, you can't believe such a thing, but it's true. You will buy it because it is just the dress that the friend you will be shopping with would want and she will convince you that it's perfect for you so that she can later borrow it. And you'll look at pictures of yourself in that dress for years to come and wonder what possessed you to ever buy such a silly thing. At full price. Don't wear things that you know in your gut do not portray who you are or what you like.
The good news is that eventually you will come to a point where you embrace your uniqueness and, at the same time, not be afraid to conform to what others like when it is something that you are also fond of. You will learn to find balance. You will become comfortable with who you are and what you wear.
And don't worry, we'll have a talk about boys later.
With love and admiration,
Your 37-year-old Self