I Can't Stop Dressing Like it’s 2003 And I Desperately Need Help

I will wear the shit out of some ripped jeans, a velour Juicy Couture hoodie and furry boots.
Publish date:
January 22, 2015
trends, advice

Once, when I was seven, my parents removed an ancient dresser with paint stains and chipped edges from my bedroom to make way for a nice, new dresser. I stayed up all night, curled up in the hallway where the dresser now sat, wailing and mourning the loss of a piece of furniture. I was a really fun kid.

While I’ve thankfully matured since then, the principal trend – my discomfort with new things and tendency to stick to what I know – continues in many aspects of my life.

I was one of the last of my friends to hop on the smartphone trend, simply because it seemed complicated, and what was an Instagram anyways? Now, when my phone contract runs up and it’s time to get a new one, I am disappointed if I can’t have the same old iPhone version I am used to. Updates and upgrades terrify me, and as a result, I remain outdated in a lot of ways.

One of the most prominent ways is my wardrobe. When I find something I like – I stick to it. It just so happens that I really liked early 2000’s fashion. I will wear the shit out of some ripped jeans, a velour Juicy Couture hoodie and furry boots. Add some big old silver hoops and a high ponytail and you have me on any given Saturday.

And while I am painfully aware that this look hasn't been in style for over a decade, I am totally clueless about how to change it.

I really love observing the latest trends. I will watch things go in and out of style, all the while wearing leggings, Uggs with the fur flipped out and my high school hoodie. I just can't keep up.

But I’m not a teenager anymore. I've watched all my friends get “real” jobs and go out in the city and drink craft beers in their peplums with statement necklaces. Meanwhile, I was waitressing, going to the same bar I used my fake ID to get into in high school, and wearing the same go-to empire waist top with the rhinestone buttons and faded jeans I’d worn back then.

But recently, I started working in an office environment. I have to wear cardigans, slacks that aren’t skintight, and nice tops. I am having an identity crisis. At 24, I had to drag my mother to the mall with me to help me pick out work-appropriate wardrobe pieces. It’s all so overwhelming –- the adult workwear, the subway, the happy hours where the point is to network and not to get wasted.

And so I come to a crossroads –- do I give in and update my wardrobe, or do I keep up my hot pink logo sweatpants and light wash destroyed flares until they rotate back into style in a few more decades? Dear readers, please help me. I am afraid to leap out of my fashion comfort zone.