I spent a glorious week in New York City earlier this month. My best friend from college lives in hipper-than-thou Williamsburg, Brooklyn, and I spent a few days with her getting to know that neighborhood and its denizens pretty well. Then I spent a weekend in the middle-of-nowhere Pennsylvania, where my best friend from high school got married. As we toured Frank Lloyd Wright’s Fallingwater house marveling at the architecture, and biking the Laurel Highlands that surrounds it, I struck up conversations with intellectuals from Japan, Russia, Israel, France, Italy and the UK. When I returned to Brooklyn, I ate up my favorite Middle Eastern delicacies and gobbled up conversations about great works of literature and laughed my ass off as artist-musician-writer types joked satirically about mass American culture. 

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.