From Jeggings to High-Waist Crops: The Evolution of Skinny Jeans

Over the past decade, skinny jeans have swiftly solidified their standing as a must-have wardrobe staple akin to a plain white T-shirt or little black dress. We’ve seen them evolve from blood-flow-constricting raw denim to glorified leggings to the flattering and comfortable stretch styles we know and love in 2020. It’s been a wild ride, filled with all kinds of ill-advised twists and turns, but we wouldn’t have it any other way. Here, a brief history of skinny jeans in all their glory.

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kate moss wearing skinny jeans
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2005: Baggy Ankle Fiasco

Skinny jeans as we know them were introduced to the mass market in 2005, but even then, they weren’t exactly skintight. Because many of the early styles were made from Japanese raw denim (meaning they’re fabricated with absolutely no stretch), they couldn’t hug our curves in the same way that denim woven with spandex or elastic can. Another consequence of this fabrication was a tendency and widespread acceptance for the jeans to pool and slouch at the ankles (a blessing in disguise for petite women who’d grown tired of getting all their jeans hemmed).

jennifer hudson wearing skinny jeans
Scott Gries/Getty Images

2006: The Bootcut Replacement

It didn’t take long for women to discover that skinny jeans and tall boots were made to go together, like peanut butter and jelly or Jennifer Lopez and Ben Affleck (RIP, Bennifer). They quickly became our new go-to for slipping into cowboy boots and slouchy wedges. Because, let’s be honest, if Jennifer Hudson still wasn’t sure whether a clean, tight line from hip to toe was cool or not, then why should the rest of us be?

amanda bynes wearing skinny jeans
Lawrence Lucier/Getty Images

2007: Accessorized With Boho Belts And Layered Shirts

By 2007, the curve-hugging cut had finally been accepted by the general population. However, we weren’t entirely sure how to style them just yet. So we slipped back into our favorite denim styling tricks of yore, like Amanda Bynes slinging a wide boho belt around her hips. Or Lauren Conrad wearing her skinnies with no fewer than two layered tanks or tees. As a whole, it felt like the women of the world really wanted skinny jeans to work but hadn’t quite worked out the logistics just yet. But still, popular brands of the moment, including J Brand, Rock & Republic, Ksubi, 7 For All Mankind and Citizens of Humanity, were pumping out one slim style after another—often for $200 or more.

rihanna wearing skinny jeans
Michael Loccisano

2008: Every Color Of The Rainbow

Perhaps in an attempt to make skinny jeans feel more like regular pants, brands like Old Navy and Express began pushing denim in every color of the rainbow, from sunflower yellow to mint green to royal purple. Maybe they thought this would make it easier to figure out how to work skinny jeans into our regular outfit rotation. Seeing as most of us look back on 2008 and wonder why we thought it was a good idea to turn our poor, hardworking legs into crayon-colored sausages, the answer is a resounding “No, it did not.”

mischa barton wearing skinny jeans
Chris Jackson/Getty Images

2009: Punk Rock Revival

By 2009, designers and stylists finally decided to return to the roots of skinny jeans to crack the sartorial code. Rock ’n’ roll musicians and fans alike had been wearing stovepipes as far back as the ’60s (with ’50s country stars wearing them even before that), so out came the fringed scarves, intricately studded black leather booties, ironic schoolboy blazers and as many distressing techniques as manufacturers could think of. See the Balmain runway collection for spring 2009 that kickstarted this exact aesthetic. The pre-worn look became the be-all and end-all across all denim styles, leading teens and 20-somethings to spend twice as much money on jeans just to have them inexplicably torn from thigh to ankle.

kim kardashian wearing skinny jeans
Ray Tamarra/Getty Images

2010: Glammed Up Denim

In fashion, the pendulum tends to swing from one extreme to the other with a certain sense of drama. So after the rock moment was over, glam was in. Cue the platform pumps, faux-fur vests, wide-brim wool hats and ladylike Hermès totes casually nestled in the crook of one’s arm. We began to take skinny jeans much more seriously as they slowly started replacing most of the other denim and pants options in our wardrobes. Brands started experimenting with all sorts of different skinny styles, like motocross-inspired embroidery (that would be Diesel), lace trim at the hem and intricate back-pocket detailing (we’re looking at you, True Religion). The denim doors were opening wide and the possibilities seemed endless.

mindy kaling wearing skinny jeans
Michelle Tran/Getty Images

2011: The Jegging Mistake

It took us some time to get here, but we could finally acknowledge the universally flattering qualities of a dark-wash skinny jean made with elastic. That said, 2011 was a sad time for elastic denim, as multiple brands postulated, If people like skinny jeans made with 2 percent spandex, then they’ll probably love them made with 70 percent spandex! And so began the era of jeggings.

What started as a highly adaptable pair of jeans transformed seemingly overnight into blue leggings with fake pockets, zippers and buttons, culminating in a horrifying infomercial for Pajama Jeans. While it was inevitable that some women would buy into the “more elasticity = more style” concept, most were able to recognize that skinny jeans were swiftly becoming a real-life SNL skit. If we wanted to regain control of our beloved slim-fit pants, we were going to have to back away from jeggings. And fast.

reese witherspoon wearing skinny jeans
Bauer-Griffin/Getty Images

2013: A Return To Classic Denim

Luckily, this is precisely what happened. Along with the rise of fashion influencers and street-style photography between 2013 and 2014 came a return to treating our jeans like the wonderfully sturdy staple they were always meant to be. Trusty dark-wash styles and classic blues with minimal distressing or bleaching were the perfect backdrop for showing off our peplum tops and Valentino Rockstud heels à la Reese Witherspoon in her post Wild glow.

jenna dewan wearing skinny jeans
Bauer-Griffin/Getty Images

2015: Shaping Technology Evolves

As smoothing and lifting technologies became more advanced, waistlines began to rise. If designers were able to make our bum and thighs look so good, why not extend those skills to assist our midriff? High-waist jeans became the number one night-out style (worn with our handy-dandy going-out tops, of course), which was particularly good news for anyone prone to post-drink bloat (aka everyone). In fact, we looked so damn good that we started wearing those high-rises all the time—to run errands, to school, to brunch—still accompanied by fun tops like Jenna Dewan’s eyelet lace crop or an off-the-shoulder ruffled blouse.

jessica alba wearing skinny jeans
BG007/Baur-Griffin/Getty Images

2016: High-waists Are In

As was the case with implementing elastic into our jeans, we all went overboard with the high-waist theme. In 2016, waists weren’t the only thing that had migrated north; hems did too. With denim enveloping more and more of our torso’s real estate, our ankles were now free to roam about in the fresh air, whether we really wanted them to or not. This was good news if you were a petite women with a long torso, but for the rest of the population, we began to look as though our jeans were staging a coup on the upper half of our body. (Speaking of, can someone please check on Jessica Alba?)

regina hall wearing skinny jeans
Noam Galai/Getty Images

2018: Wide-leg Crops Start To Outshine Skinny Jeans

Unique washes and undone hems became the style du jour once again, but this time around we were well versed in the most flattering places for distressed holes or fading. We were now aware that just because we could tear jeans to shreds didn’t mean we should.

Around 2018, skinny jeans started to fall out of favor and were replaced by wide-leg crops, mom jeans and straight-leg styles. Normcore began its slow, creeping campaign for wardrobe domination, and skinny jeans were among its first victims. It’s not that super slim jeans were fully out of style (not by a long shot), but they were no longer the top dog in denim. After all, why squeeze our legs into spandex denim tubes when we can feel the breeze on our calves with a nice pair of culotte-inspired jeans?

chrissy teigan wearing skinny jeans
UMV/Star Max/Getty Images

2020: They're Still A Closet Staple

As we enter the roaring ’20s, skinny jeans still haven’t regained their spot at the top of the denim food chain, but that doesn’t mean we don’t like to wear them on the regular. Waistlines are dropping a bit lower, no longer letting our belly pooch hang out or covering everything up to our bra band. The super-flattering and elongating pairing of black-wash denim with black booties has been fully realized and embraced. Much like the little black dress or a classic trench coat, skinny jeans can officially be called a timeless wardrobe staple and something you can never really go wrong wearing.



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...