Finding My Style at 29

I started to write about our night out on the town last night but got distracted looking at kimonos and jumpsuits I want to buy. Which got me thinking about style. I’ve been actively searching for “my style” for about two decades. It has dawned on me recently that I probably don’t have just one style, which is why I feel no closer to finding it than I did when I was 10 years old and carefully observing what the girls in my favorite movies wore so I could attempt to replicate the look. I’m a Gemini for goddess sake! Some days I want to wear a gorgeous kimono with a pair of stacked black heels; others jeans and my well-worn Birkenstocks; others athleisure to the max — plus everything in between. And let me tell you a secret: when my outfit is aligned with how I want to feel (i.e. bright red jumpsuit = on my game) I am unstoppable. There’s something about dressing the part that reminds me what I’m made of, I suppose.

I’m also a Virgo (rising) which means I crave order and love the idea of having a capsule wardrobe or a self-imposed uniform. I think I only like it in theory though (can you imagine how tidy the closet would be?). To only have, say, 10 items of clothing to choose from feels stressful. What if the occasion calls for something else? What if I don’t feel like wearing that on a given day? What if I start to feel suffocated of choices? And yet the appeal of not having to decide on what to wear or, at least, not having very many options to choose from is also there. I’ve considered these as potential minimalist wardrobe options: jeans, tank top, kimono, heels; only jumpsuits; yoga pants, workout top, hoodie; max of 20 items in bright tones to mix and match; max of 10 items all in black. What happens every time, though, is I remember how deeply I adore variety. The Gemini’s need for freedom outweighs the Virgo’s quest for organization. At least for now.

Since I’ve already talked about my sun and rising signs, I may as well share that my Libra moon insists that I have a taste for nice things and that I am a highly emotional decision-maker. Once, I went into Saks Fifth Avenue and just pretended I was shopping there. I fell in love with a black jumpsuit — a $575 piece of cloth that I thought I would die if I couldn’t buy. Well, I didn’t buy it and I didn’t die but I do still think about that jumpsuit and the way it made me feel to be wearing a piece of clothing that cost as much as my car payment. (It felt really good.) Being emotional about clothing is something I cannot escape; at least 5 times a year, I frantically sort through my closet because I’ve realized I have nothing to wear. Maybe I’m missing a seasonally appropriate party dress or a pair of shorts that I like or I decide I hate everything I own and absolutely have to start over. Or I’ll put on an outfit I’d been planning to wear for a certain occasion and realize that it doesn’t fit right, or look the way I wanted it to, and I will feel an inescapable amount of frustration and emotion fill my chest.

Curious as to why I feel so triggered by clothes, I trace back to my middle school days of school shopping with my parents. 75% of the time, we bought our clothes at second-hand stores. At the age I was, as the person I was, being dragged to the thrift store and told to pick out the clothes I was going to wear to school all fall was humiliating and torturous. I knew I wasn’t going to find the kinds of clothes the girls in movies wore at Goodwill. And rarely did I. Instead, I was left with a pile of musty jeans and shirts that never fit quite right. I spent my days at school feeling awkward and wishing I’d be adopted by parents who took their kids shopping at dELia’s and PacSun. To have clothes that looked amazing was to be amazing. This belief of mine was unshakable. Of course, this meant that my fragile sense of self as I entered high school was contingent on how cool I looked and felt. Since I never felt or (from where I stood, facing the mirror) looked cool, I became increasingly insecure. You may have never known it from the outside: I wore a pink and brown plaid mini skirt over my jeans in an effort to pull off my own twist on Avril Lavigne’s punk babe vibe. I acted like I didn’t care but I cared so, so much.

The other 25% of the time my parents took us to JCPenney’s or Kohl’s. My mother, being the kind of person she is, took obvious pleasure in the fact that I was having a full-blown breakdown in the JCPenney's dressing room. She was making me buy shorts but, instead of letting me get the cutoffs I wanted, she established a rule that my shorts must not be any higher than my fingertips. This was an attempt at enforcing modesty that ultimately pushed me further to the edge they didn’t want me to be on than I probably would have gone on my own. I remember being furious and embarrassed and not being able to control my emotions about it. Crying and begging my mother to let me just dress like the other girls was a low for me. I was 14 and this was such a formative time for me to be able to explore who I was and how I wanted to express myself through clothing. Dressing rooms quickly became a place that immediately heightened my fight-or-flight response. They still do at times.

It’s a wonder I didn’t end up in fashion in one way or another; my obsession with it over the years is only obvious to me now that I’m looking backward. As I round the corner to 30, I am transported back to the transient feeling between girlhood and womanhood. This birthday is a rite of passage out of being a twenty-something; I’m certain that moving into this new decade will unlock a sense of purpose and certainty in both my emotional life and the life of my closet. If you were to look at my closet right now, you’d agree that it needs some work.

The only issue with this is that I am terrible at shopping. I get overwhelmed easily, usually end up buying something that can be worn with either one or zero other items I own, and become decidedly the most critical and hopeless version of myself. I love how the right clothes make me feel but I can’t for the life of me seem to choose the right clothes. A red biker jacket I loved in Banana Republic hasn’t been worn but once because, well, what do I wear a red biker jacket with? This is a combination of problems: not knowing what to buy because my style is a scattershot at finding the version of me I want to be on any given day and a lack of both patience and logistical style knowledge (what kind of top looks best with a pair of faux leather leggings? Beats me.).

You can see my dilemma. I know it may seem obvious to some — just buy and wear what you like. It should be that simple but, for me, it’s not. The formative years of my fashion life were spent in used Levi’s and collared short sleeve shirts from a (likely to be defunct soon) department store while I hoarded clothing catalogs I signed up for on a computer at school. These were free, fashion magazines were not. For those, I’d go to the library and spend hours looking at back issues, forever perpetuating how behind I felt (feel) when it comes to trending fashion.

Perhaps it is only in my head that I am at odds with having a style that suits me. But isn’t that all that really matters — what we think of ourselves in the clothes we adorn our bodies with? If I’m not feeling the style that I currently inhabit (I don’t), isn’t it my right and privilege as a woman and a being of this earth to explore more fitting options? I think so. And I have come to understand that each phase of my style journey has served me in some way. We are meant to shed and grow new skin every so often; it’s growth. I am using this approaching birthday as a portal into the next evolution of who I am, releasing all old beliefs about myself and clothing; whatever comes next may only last for a few months or it may take root for years. I guess only time will tell. If you know of a personal stylist, DM me.

♥ CV