It’s important to ask yourself the questions that truly matter in life: Why was I put on this earth? How can I best help others? Who exactly am I and how would my personal style be summed up by one of those online quizzes?
You know the kind: "Trendy and Bold," "Laid Back and Bohemian," or "Classic, with Modern Updates." Descriptors that previously I found rather vacant and unhelpful because previously I wasn’t facing the daily crisis of having absolute freedom as to what clothing to put on my body.
For my first job out of college I worked in an office and dressed like it. Technically, I believe our dress code was "business casual," which is a largely ridiculous and contradictory term. When someone says that, they really mean, "You don’t have to dress like a humorless divorce lawyer, but kind of." That is to say, any sense of casualness is a lying lie as far as I’m concerned. I’m not convinced the line separating "business casual" and flat out "business attire" is really worth distinguishing.
Naturally, the first order of business was using some of my graduation money to buy a pair of Tory Burch pumps with a rounded toe and sensible heel because it was 2011 and that’s what you did. I believe I wore them four times. I approached dressing for that environment like a chore that had to be completed — joylessly dragging myself to the Ann Taylor Loft sales to buy a new pair of slacks because business ladies wear slacks, right? (Honestly, there’s nothing wrong with Ann Taylor Loft, but there is something profoundly bleak about shopping at Ann Taylor Loft when you don’t want to be.)
Had I cared more or perhaps possessed more financial resources at the time, I might have had some fun with my professional clothing phase — developed a real style of my own. Would I have been "Scandal"’s Olivia Pope with her neutral colors, chic wide-cut pants and blazers? Or perhaps I would’ve been more like Jessica Pearson from "Suits" in her perfectly tailored dresses, sky-high pumps and unexpected embellishments. Instead, I asked myself things like, "Would this sweater maxi-dress count as business casual if put a blazer on over it?"
About a year into my "business casual" job, my boss’s boss told her: "Kara should dress for the job she wants." She did not know that the job I really wanted was one where, "like, I don’t know, you can wear whatever." That dream mostly came to fruition when I moved to Los Angeles where the climate and the general vibe of the city asked much less of my sartorial decisions. More relevantly, I began a job where I exclusively worked from home and I leaned very hard into that aesthetic.
I lived a casual, comfortable life, mostly from my couch and, dammit, I dressed like it — investing in multiple sets of premium pajamas, as one does. There was also a barrage of athleisure purchases because many of my days consisted of wearing pajamas all day, going to the gym and putting those pajamas back on.
However, everything comes to an end and I am back to moving through the world, out in public, along with other human beings and I now find myself at a fashion precipice. Let me tell you, freedom is a burden. My new dress code has no rules or even sketchy guidelines beyond general appropriateness — an assumption I’m making on my own since it was never explicitly specified. And because I can wear anything, I of course now find myself with nothing to wear.
Do I lean into the sporty, casual, streetwear-heavy look I started cultivating around 2009 to match Rihanna? Am I one of those L.A. cool ladies in flowy Free People blouses and sundresses? Am I a skirt person? Should I invest in even more denim? For a brief period, I dabbled with becoming an “interesting jacket person”— jeans and a casual top under a bold jacket and some sort of interesting but non-flashy shoe. Maybe I’ll be the slouchy button-down girl and buy tons of slouchy button-downs. I am no longer limited to corporate guidelines, function, practicality or weather. This ship could go anywhere.
When your life starts to look different, it’s only natural to feel the urge to look different as well. This new version of yourself — in your new job or new city or new neighborhood — provides the opportunity for a reset and despite how time-consuming, anxiety-inducing and financially irresponsible it may be, you can’t deny it’s exciting. Perhaps you can use this transition to truly become a dress woman. And not just a woman who wears dresses, but you can embody the spirit and energy of a woman with the togetherness, taste, and dry-cleaning schedule to be a dress woman.
In an ideal world, I’d walk into some random boutique exactly in my price range and discover that someone has perfectly curated the exact style I didn’t know was mine —one that perfectly encapsulates this new Kara in her new world. That would be ideal and I’ve had literal dreams about it. But until I find this Goldilocks shopping experience, I’m going to continue doing a ton of online shopping and sending things back — though only with retailers who offer free returns, of course. I’m still me.
