I don’t wear leggings anymore.
Like most millennials, I spent most of my twenties and early thirties happily ensconced in leggings: the soft/stretchy kind for casual day-to-day fashion, and the compression/yoga kind for everything else.
As a personal trainer living in NYC, this was my self-selected uniform: leggings, sports bra, flowy top, hoodie.
I owned literally dozens of pairs of leggings in a wide variety of styles, and I found them both flattering and practical. I liked the fact that I could move around in them without anything shifting or bunching up, and I remember the sensation of being “held” making me feel safe.
That said, at least part of what I enjoyed about wearing leggings came from a rebellious, troll-y place.
I loved how leggings represented my generation’s informal fashion ethos, but I also loved how they seemed to horrify boomers and modesty advocates alike, and found it both satisfying and hilarious how easy it was to offend people who didn’t think leggings should “count as pants.”
There was something so empowering to me at the time to dress in ways that directly challenged the idea that women’s bodies are innately sexual and dangerous to the fabric of society, and that women should “cover up” to avoid harassment and disrespect.
“My body is my own,” my leggings told the world. “I’m not responsible for men’s feelings or actions, so if seeing the outline of my butt offends you, I suggest you look inward and get curious about why that is!”
Despite being a diehard leggings fan for more than a decade, however, things started to change for me a few years ago when adidas reached out to me to do a brand partnership deal, and gave me the opportunity to try out some new styles and sizes that were more sporty, slouchy, and unisex than what I was used to wearing. (I recommend checking out their women’s workout clothes if you’re looking to update your wardrobe too btw!)

It was so fun to explore my gender identity in new ways while coming to the conclusion that I’m non-binary, and looking to express myself differently through clothing. I realized that a lot of my wardrobe had been collected when I was still following certain unconscious rules for looking “appropriately feminine,” and I was curious to know what my personal style might look like if I gave those rules up completely.
I was fascinated to discover that, despite being almost a decade into body neutrality at that point, I was still following a long-held unconscious “rule” for how to dress (or at least, for how I thought I “preferred” to dress), which was actually rooted in both self-objectification and internalized patriarchy.
The rule came from a belief that wearing baggy clothes would be “unflattering” on me, and that I had to wear something a bit more form-fitting in order to avoid looking frumpy, dowdy, or masculine– god forbid! (Lol.)
Once I realized that I actually no longer felt any obligation to conform to conventional ideals of attractiveness or femininity (and that, in fact, looking more masculine sounded delightful to me!) this outdated “rule” seemed to evaporate into thin air.
As a result, I found myself rewarded with the freedom to choose from a much wider variety of clothing sections, styles, and expressions.
Over the course of multiple years I thought critically and deeply about the way I express myself through clothing, acquired some new clothing to try out different looks, and learned a lot about what feels authentic and empowering to me at this point in my life.
As it turns out, leggings just… didn’t make the cut.
I never set out to stop wearing them or anything, I just noticed that I was going to that drawer less and less often, feeling drawn instead to looser fitting bottoms, sporty unisex vibes, and oversized options.
As my closet started filling up with sweatpants, track pants, joggers, and adventure pants, I found it easier and easier to put together outfits that felt joyful, comfortable, and affirming (whether for the gym, going out, or just lounging at home), and I eventually put most of my leggings away into storage.
Admittedly, overhauling your style can be expensive and time-consuming, so there is a huge amount of privilege in the fact that I’ve been able to do it, but looking back I can say with confidence that it was so, so worth it.
What’s your personal relationship to style and self-expression been like lately? Have you ever suddenly found yourself moving on from a long-held style staple like this?

Big hug,
Jessi
PS:Don’t forget to subscribe to my Patreon at the $25/month level to access my newest module of the Highly Sensitive & Thriving course material on April 1st! This month’s webinar and accompanying worksheets will walk you through exactly how to protect your peace—which is to say: avoid or reduce the overwhelm and overstimulation that plagues so many highly sensitive people—through preventative and structural boundaries!
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