I’m not the first to talk about this on the post calvin, but after a year of pondering and coming back to Katie Van Zanen’s piece on fashion struggles, I’ve realized how much I resonate with the conundrum of what to wear.

To put it simply, I don’t know how to dress anymore. I don’t know what my personal style is, or perhaps what I want it to be. As if being in your twenties isn’t confusing enough, ever-changing fashion trends seem to throw yet another wrench into the quest for confidence and a sense of self. It’s difficult for me to tell if I’m drawn toward certain clothing items because they’re on trend or because I actually like them.

It’s not just that I don’t know how to dress—I don’t know where to shop. I’m giving StitchFix a try, though I haven’t had very much success thus far. I’m not sure what happened to Target, but shapeless prairie dresses aren’t my style. I don’t really feel comfortable in crop tops and mini skirts, which seem to be in abundance at most stores. Department stores in general confuse me these days. The juniors’ section makes me feel like I’m clinging to my high school days while the women’s section feels like too far of a leap into the future. For now I remain in this awkward in-between.

I used to think I had it all figured out. In middle school, I developed an obsession with the fashion industry. I studied up on the lives of Coco Chanel and Donatella Versace and Yves Saint Laurent, absorbing countless since-forgotten facts about their designs and brands. When it came time to do a school presentation based on our passions, I created a lengthy powerpoint presentation about the industry. Teen Vogue became my sartorial Bible. I even told everyone I wanted to be a fashion designer when I grew up.

It’s kind of humorous—maybe even painful—to reflect back on my naïveté and realize how out of touch I am with fashion today. I can’t fathom myself living in New York City and spending my days sketching designs or selecting patterns. Instead I’m helplessly clinging to my skinny jeans while trying to decide if I can pull off puff sleeves.

As today marks the first day of fall, I’m tempted to reassess my closet and invest in some new items for the season. I still don’t know how to go about this, though. Maybe I’m overthinking a bit, and maybe my struggles are rooted in a deeper concern of caring too much about what other people think. Like Katie put it, “I would like everyone there to believe good things about me, and I would like my outfit to communicate somehow that I am young and successful but also mature and kind and definitely cool.” It’s a fine line to walk, but for now I’ll keep trying—albeit one potentially unfashionable step at a time.

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