Let me first say this: I was not a fashionable teenager. To be honest, I’m not sure any  teenagers are… The ones I see who are trendy look totally ridiculous. I think your school becomes your own little world, and whatever is cool there, you think is cool everywhere.

Which isn’t actually true.

Any kid who’s been moved from city to city while in middle and high school can tell you that. One brand is hot in one city, and kids in another city have never even heard of it.

But what happens is the one kid who has the balls to wear something new and be confident in it is the one who sets the trends. I’m not talking about the kids who dress purposely ugly (goths spring to mind), ridiculous (Uggs in the summer? Really?), or skimpy (enough said).

I’m talking about that girl who seems to wear whatever she likes, and then everyone wants to wear it too. That girl. Be that girl.

Here’s what I’ve figured out about following trends.

They aren’t you, and you’ll feel uncomfortable and look uncomfortable in them.

When I was in high school, around 10th grade, I finally came around to “normal” clothes after an ill-advised stint in novelty t-shirts and big jeans. I started dressing like all the popular kids. In those days, it was khakis from The Gap and Doc Martens sandals. It wasn’t me, and I still didn’t really fit in. I didn’t figure it out until much, much later in life. I never looked good in them because I never felt good in them.

Not all trends are all that flattering.

(Bubble skirts pop into my mind.) Pick clothes that actually look good on you. I kept trying to pick clothes that looked like what I saw in magazines or catalogs, but they looked horrible on me. My mom would do this thing when she took me shopping, where she would pick up something I didn’t like and say, “Humor me.” Which loosely translated means, “Go try this on or you’re not getting anything.” Then, if it looked good, she would say, “That looks so becoming on you.”

Becoming on you. Not really the words every teenage girl is dying to hear in the dressing room. But she was onto something. There are lots of beautiful clothes out there. Just because you put them on, doesn’t mean you’ll look beautiful in them. It doesn’t mean there’s something wrong with you. It just means that some clothes look good on certain shapes, lengths, and sizes of woman. There are some clothes that just don’t look good on anyone. Period.

Pick stuff you like, whether anyone else likes it or not.

Now, this piece of advice, I sometimes followed and sometimes didn’t as a teenager. Sometimes I followed it to my own detriment (like the Star Wars athletic tee I wouldn’t take off for most of age 15), and sometimes I didn’t follow it, also to my detriment (see above, where I wore clothes because they were trendy).

The times in my life I remember enjoying my style, and consequently felt the most confident, is when I wore what made me feel good. A lot of times it included really, really short hair, which didn’t always thrill my mom and certain types of boys, but I pulled it off because I felt good in it. I actually kind of rocked the short hair.

Cultivate a personal sense of style.

I spent a lot of time trying to look exactly like things I saw in magazines and catalogs, but that stuff passes. What’s hot today isn’t hot tomorrow. And then you wasted money on clothes that aren’t cool anymore. And you just got them like, last month. (I still make this mistake sometimes. That’s why I have 5 embellished t-shirts in my closet that I just got 6 months ago and probably won’t wear ever again.)

You’ll find items that you’ll literally cry over when something irreparable happens to them. I’m not talking about materialism; I mean pieces of clothing that you feel like are a perfect representation of you and your own style, that make you look and feel great. Look for things like that, and hang onto them.

The girls I remember wishing I could look like weren’t following trends or letting what everyone else was wearing dictate their style. Well, they weren’t trendy anyway. There was just something about them… they were comfortable, they owned their look, and most of them probably still do today, over a decade later.

Find your own clothing personality, and live outside of the trends. Ironically, this will make you the trendsetter.

Just a little advice from the me I am now to the me I was then.

This is the first post in a series called Letters to a Teenage Girl. Read the intro here.

I’m not happy with my personal style lately. It’s sort of been ongoing since I got sober and lost some weight… and you know, stopped spending all my money on booze. I’ve told myself that part of the problem is that I don’t have a lot of money to spend on new clothes, but I think there’s a little more to it than that. I would say the real problem is that I don’t give it much thought until I’m actually in a store, ready to buy some item that I need. Seeing as I give almost everything in my life too much thought, I thought that was a little ironic.

Whether we like it or not, we’re judged at a moment’s glance by our outward image. And as much as the BF hems and haws about appearances not mattering, he plays by the rules and wears a suit to the office every day, even Fridays. In our careers, in dating, we’re judged first by our appearance and our clothing does a lot of the talking. (I wasn’t sure if I was attracted to Date #4 when we met – he was wearing a suit and I always say that it blocked any read I was trying to get from him.)

I’ve been watching the preliminary back-to-school ads roll in, and it amazes me how much time and thought middle and high school kids put into their clothing choices. Their clothes (in their minds) say so much about them – what group they belong to, what kind of music they listen to, what their socioeconomic status is, how in tune they are with trends, which causes they support (if any). Why this is, is an entirely different subject that I don’t wish to touch on here. What it did, though, was prompt me to look at my style choices and think about what they said about me.

That’s when I realized that my style choices weren’t really so much choices as they were lazy acquiesces. I live in a town with few clothing options, but I’m not sure I would be much better off anywhere else.

I love:
Blazers
3/4-sleeve jackets
Cardigans
Dark jeans
Vintage-y blouses
‘40s inspired dresses, shoes, hair… well, anything really
Splashes of bright color
Scarves
Preppy-style flats
Colorful, vintage heels
Long dresses

How much of this do I own? Er… none. I do have a few cardigans, but they’re pretty much a necessity in my 60-degree office. Oh, and I own about 7 pairs of dark jeans, but all in the same style and cut from the same store. Even I know that’s wrong.

Looking at this list, I can see that this is actually how I used to dress in high school. My mom hated taking me shopping – I never saw anything I liked unless we were at a Goodwill. Luckily, times have changed and Anthropologie picked up what I was throwing down. Anyhow, I did think that it said something about me. Like today’s teenagers, I was keenly aware of the message I was trying to send. I was eclectic, creative, a little hip, a little bohemian, a non-conformist, an intellectual.

How many of us can say we put that much thought into our wardrobe post-high school or college? I grab whatever Express is offering that month in the way of office-appropriate attire within my budget and that’s about it. Wouldn’t it be nice to have a personal style again?

It’s not just about sending an arbitrary message about who I think I am. After all, if you’re worthwhile and think I’m worthwhile, we’ll get to know each other and you’ll figure out who I am. When my outer self matches my inner self, who it is that I am, I’m a lot happier. Plain and simple, if I actually enjoy the clothes I’m wearing, then I’m a lot happier overall. I also feel a lot more at home in social situations. I feel more comfortable projecting who I am when I’m not tugging on uncomfortable clothes that don’t fit right. And, of course, I wouldn’t mind standing out from the crowd a little.

In an age when personal branding seems to be all the rage, why are we sticking ourselves in the same suits and brands as everyone else? Why aren’t we spending more time thinking about how our “look” corresponds to our personal brand, our goals, and where we want to go?

Some questions to ask yourself about your personal style:
• How would I like people to see me? Use descriptive adjectives: polished, bohemian, put-together, artsy, sleek, glamorous, etc.
• How would I describe myself in a few words? Are you a corporate go-getter, an intellectual, a tech geek, a trendsetter, outdoorsy, creative?
• What styles do I identify with? What words describe them? Do those words describe me?
• What are some items I really like? Do I currently have them in my collection?
• How do my clothing choices affect me on a daily basis? Am I happier when I wear certain colors? Certain styles?

Me, personally, I’m going to start holding out for items that fit with my now clearly defined personal style. Now, if you’ll excuse me, I’m going to rethink those 7 pairs of jeans…

All images from Anthropologie.com.