I remember the first time I put on a pair of leggings. It was the early 1990s when they started sneaking their way from dance studios onto high school campuses—Stretchy, form-fitting, and oh-so-flattering (or so my 15-year-old self thought). I squeezed my curvy teen bod into a too-small, neon pink pair and pranced around feeling like hot stuff, never mind the muffin top spilling over the waistband. Little did I know those leggings would kick off a rollercoaster three-decade-long relationship.

You see, I hit puberty before most of my classmates. While the other girls were still rocking cute training bras, my mom dragged me to the “women’s sizes” section. So, when lean, leggy supermodels strutted down runways in the early 90s modeling the “heroin chic” look, I felt worlds away, taking up too much space in my XS t-shirt.

But then leggings came along and changed the game. They hugged every inch of my thick thighs and a bubble butt that jeans squeezed and gapped at. I’d throw them under an oversized sweater with combat boots and scrunch socks when running errands or going to school. I felt almost - dare I say skinny - gliding around in my body-con second skin.

My 90s high school experience became a mashup of Clueless meets Friends fashion. While teens don hip-huggers and crop tops today, I lay leggings under baby doll dresses and overalls. I’d finish it with choker necklaces piled high and scrunchies wrapping my hair in a messy bun. Even with curves that garnered nicknames like “thunder thighs,” for once, I felt almost stylish next to my petite gal pals.

As I marched through my 20s, leggings tagged along as a versatile wardrobe staple. They became an anytime, anyplace, and anything-goes type of garment alongside flannels and combat boots as grunge culture boomed. Simultaneously, dance and athletic attire crazes made leggings double as streetwear.

During those early days out of braces and out from my parent’s house, I pushed the limits on appropriate leggings environments. The sheer spandex variety debuted under miniskirts when I hit the club with friends. Perhaps they offered a little too much cheek during lectures as an undergrad. Maybe an interviewer or two caught a glimpse of my whale tail when I leaned over a conference table. What can I say? Hindsight is 20/20, but at 20-something, I gave zero f***s.

Heading into the Y2K era as a single thirty-something, my leggings obsession shifted gears. By now, they felt more like an old friend I kept inviting to hang out rather than a daring fashion choice. I welcomed the growing athleisure trend with Lululemon yoga pants that cost more than my car payment.

Letting go of the 90s matchy-matchy style rules, I’d pair those yoga leggings with slouchy tunics and puffer vests on the day-to-day. Was it cute? Questionable. But it lets me roll out of bed, slip something on, and be on my way - no squeezing into waistbands or fussing with uncomfortable fabrics.

Over time, chasing a toddler and climbing the corporate ladder in leggings and tunics warped my fashion sense and self-image. Muffin tops turned into full-blown donuts around the middle. My butt sagged after years of making leggings do most of the lift and shape work. Shopping became frustrating as I sized out of the “average” woman’s section, but styles I liked never came in “plus.”

I made attempts to re-introduce jeans on weekends or for date nights. But pulling rigid denim over my wide hips and thick thighs felt miserable. So, I’d default to leggings or sweats and throw on an oversized sweater, hoping it gave the illusion of an hourglass rather than an apple.

Not going to lie; as I crept closer to 40, I caved into societal bullshit, believing I had let myself go. I carried that negative mind chatter into changing rooms where nothing tighter than leggings and a hoodie triggered terrible feelings. Those perfectly posed mannequins with their perky fake boobs and sculpted plastic abs taunted me under the fluorescent lights.

Rationally, I knew bodies change. Priorities shift with age - for me, from partying to parenting. What message did I send my daughter when criticizing my post-baby soft tummy but applauding her perfect little toddler belly?

Still, I clung to leggings through my 40s as self-love and self-care anchored themselves on my priority list. Tunics got longer; leggings rode lower, and sizes crept up. The number inside didn’t matter; feeling comfortable did. By now, Aligns and yoga pants make up 90% of my wardrobe.

But recently, it was time to pump the brakes on the leggings train. The catalyst happened after an indoor cycling class when I found myself sweaty and red-faced, struggling to peel off a too-thick pair of compression leggings that had taken on a life of their own. I threw them directly in the trash when I got home.

I’ve since purged my drawers of almost every pair. Sure, some basic black ones lived to see another Peloton class or errand run under dresses. But the printed pairs, the bold colors, the cheap see-through ones? Thanks for the memories in the donate pile.

Bidding farewell to my legging addiction felt bittersweet yet empowering. High school me needed their confidence-boosting powers through awkward phases. College me appreciated their reckless, rule-breaking spirit. Working moms will forever salute their comfort and practicality.

But in 2024, I seek balance and intentionality in my wardrobe and mindset. I’ve realized well-fitting leggings provide temporary smoothing and compression while self-love and acceptance shape lasting beauty.

In their place, I’ve welcomed jeans specially designed for real women’s bodies. I incorporate new bra styles that offer lift and support, so dresses skim over lumps and bumps instead of gripping them. Tommy Bahama shirts in fun prints replaced all the shapeless tunics. Sometimes, I even swap my Nikes for cute sandals or boots so my feet remember what it feels like to wear authentic shoes!

I’m focusing less on hiding behind oversized silhouettes and leaning into carefully curated pieces that feel good mentally and physically. Most clothing items still have some spandex woven in to avoid constriction. But more relaxed fabrics, breezier fits, and elevated basics align better with my current lifestyle.

Letting go of my leggings, the security blanket exposed my nerves about starting over with a more intentional wardrobe. Yet the “fake it til you make it” badassery of my younger, legging-loving self still lives inside me.

I know I’ll probably slip back into my leggings addiction as fashion evolves or if my body changes down the road. For now, though, replacing decades of reliance on their soothing powers with self-love feels like an overdue evolution. It’s not you, leggings - it’s me. Wish me luck out here in this brave new world beyond stretchy waistbands.