The Denim That Built My Style

1990s: Field’s Floors and Levi’s Legends

In the ’90s, State Street was my runway and Marshall Field’s was my backstage pass. The minute those revolving doors whooshed behind me, the smell of perfume samples and polished marble wrapped around my teenage brain like a promise. Up the escalators, past the china and the handbags, until the air shifted into that familiar cocktail of denim dye, new cotton, and a hint of metal from hundreds of zippers and rivets.

That’s where I met the holy trinity: Levi’s 501s, 550s, and 901s. The numbers sounded like secret codes, and honestly, they were. 501s were the classics: button fly, straight leg, the pair you wore when you wanted to look like you didn’t try too hard but secretly did. The 550s were my comfort zone—roomier in the thighs, relaxed but not sloppy, like the jeans version of your favorite cousin. And then there were the 901s, the wild cards with that high waist that felt half retro, half future.

I’d grab an armful in different washes—rigid dark indigo, perfectly faded blue, the occasional risky stonewash—and stake out a fitting room. The curtains never fully closed, the fluorescent lighting was rude, and the floor was littered with security tags and abandoned hangers. But when a pair of 501s buttoned just right, skimming my hips and hitting that magic point at the ankle? The mirror softened. My posture straightened. I’d twist side to side and think, Okay, this is who I am this semester.

Baggy Era: Denim Bigger Than My Doubts

By the mid ’90s, the silhouettes got bigger as my world did. Hip-hop blared from boom boxes, and the South Side sidewalks were runways for oversized everything. My Levi’s 550s became my bridge from “nice jeans” to full-on baggy. I’d size up on purpose, letting the denim pool over my sneakers just so, the hems fraying into soft, shredded tassels that told their own story.

There was something revolutionary about all that fabric. My body, suddenly swaddled in volume, felt less like a problem to solve and more like a shape still in progress. I could tuck in a tiny tee or swim in an oversized sweatshirt, and the jeans held it all together. The sound of that loose denim swishing when I walked was a quiet soundtrack of defiance against every magazine telling me to be smaller, neater, nicer.

Back at Field’s, I’d dig for the baggiest washes, hunting for that sweet spot between “I borrowed these from my older cousin” and “I definitely did this on purpose.” The sales racks made their own music: hangers clacking, security tags knocking together, the low murmur of other girls also trying on new versions of themselves. Every time I sized up, I felt like I was choosing myself over somebody else’s idea of who I should be.

Overalls & DKNY: Denim With a City Girl Swagger

Then came my overalls era, which I maintain is a personality type, not just an outfit. Bib front, big pockets, one strap casually unhooked because that’s what the cool girls did on BET. I’d layer striped tees underneath in the summer, turtlenecks in the winter, always with the cuffs rolled just enough to show off my boots. Those overalls made getting dressed feel like play again, like elementary school but with better lip gloss.

Somewhere between the overalls and adulthood, DKNY stepped onto the scene. Their bootcut jeans were my first taste of “grown woman” denim—sleek, city-ready, with just enough stretch to survive a full day on the Red Line. Pulling on a pair of DKNY bootcut jeans felt like boarding a flight to New York without ever leaving Chicago. The flare skimmed over my heeled boots, the waistband hugged but didn’t pinch, and suddenly I was imagining myself striding down State Street like it was SoHo.

DKNY also quietly introduced me to what would later be called “mom jeans.” Back then, they were just high-waisted, slightly tapered, a little ankle-baring if I rolled them right. They sat at my true waist, hugging the soft curve there, and for once the mirror didn’t feel like an enemy. Those jeans held me in without erasing me. They gave me permission to have a stomach, to take up vertical and horizontal space, to be both fashionable and comfortable on a Tuesday.

Calvin Klein & Guess: Details, Washes, and Quiet Flexes

My Calvin Klein phase arrived right on schedule, along with a stack of fashion magazines and a growing collection of department store reward coupons. The straight-leg Calvins were minimal on purpose—no wild stitching, no screaming logos, just clean lines and that tiny patch on the back that whispered instead of shouted. Pulling them on felt like putting on punctuation: simple, precise, finishing the sentence of whatever top I’d chosen.

The bootcut Calvins were another story. They swung a little when I walked, dark denim brushing over my shoes in an arc that felt almost theatrical. In the fitting rooms at Field’s, I’d try them on with different tops from the juniors’ section, watching how the dark wash sharpened a white tee or mellowed a bright sweater. Those jeans made me feel like I had somewhere to be, even if I was just heading to the food court.

Guess, on the other hand, was pure attitude. Their washes had personality: sandblasted thighs, whiskering that looked like it had a backstory, blues that faded from lake-deep to sky-light in one leg. The signature details were the best part—that little inverted triangle on the back pocket, the playful stitching, the occasional zipper detail that served no purpose except to say, someone cared how this looks from every angle.

Finding the right Guess pair at Marshall Field’s was like winning a quiet lottery. I’d slide them on, do the classic fitting room dance (squat test, sit-down-on-the-bench test, can-I-breathe test), and when they passed, I’d smooth my hands over the front like I was sealing in the moment. Walking back onto State Street with that green shopping bag in hand, tissue paper rustling, I felt like I was carrying a new chapter of myself out into the city air.

Today: Rotations, Recalls, and Denim as a Diary

These days, my closet holds a little of everything: a perfectly broken-in pair of Levi’s 501s that cuff just right above ankle boots, a slouchy 550-inspired pair for coffee runs, a modern nod to 901s that pairs high waist with soft stretch. I still love a bootcut on days when I want to dramatize an entrance, and I keep at least one “mom jean” in rotation for afternoons when I want my clothes to feel like a hug.

Every wash carries a mood. Dark indigo when I’m focused. Faded blue when I’m nostalgic. Stonewash when I’m leaning into my inner ’90s video extra. The hardware, the stitching, the way a back pocket is placed—these little details still matter to me as much as they did on those long-ago Field’s fitting room marathons. I may not be combing the juniors’ racks anymore, but I still chase that specific rush of pulling on a new pair and recognizing myself.

When I walk past where Marshall Field’s used to glow on State Street, I swear I can still hear it: the click of hangers, the escalator hum, the low mutter of shoppers negotiating with their reflections. Somewhere in that invisible archive is teenage me, tugging on Levi’s and Guess and Calvin Klein, learning that the right jeans don’t fix your life, but they do make it easier to walk through it like you belong.

Denim has become my unofficial memory-keeper. I remember field trips by what I wore (overalls, one strap down), college weekends by the frayed cuffs of bootcuts, new jobs by the stiff creases of first-day dark wash. Even now, when I slide into a pair that fits just so, I feel all those earlier versions of myself lining up, nodding in approval. The fabric may fade, the trends may shift from baggy to skinny to “whatever we’re doing this year,” but every waistband I fasten is a reminder: this body, this city, this history—they’re all stitched together, and I get to wear the story.