How to wear the Y2K trend: mini skirts, low rise jeans, denim-on-denim

Written by Cheryl Fenton

Updated August 25, 2023

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With apologies to the zany ‘80s, no style era has made us do a double take more than Y2K fashion. Referring to the late ‘90s/early 2000s, the fashion world was driven by over-the-top pop culture style icons like Christina Aquilera, Brittany Spears, and Paris Hilton. There was tons of pink (the OG Barbiecore), bedazzled logos, tracksuits galore (or should we say velour), and low-rise everything.

“A lot of people actually believed the year 2000 was going to be the end of the world, which I think was reflected in this ‘anything goes’ mish-mash of style,” says Avery Plewes, costume designer on Netflix’s new crime/drama mini-series Painkiller, a show that continues to fuel our love of ‘00s style alongside other series such as HBO’s Euphoria. For the series, which explores the beginning of the opioid epidemic, Plewes sourced vintage pieces from Tom Ford for Gucci, Yves Saint Laurent, Diesel, Calvin Klein, Donna Karan, and Juicy Couture to get the right nod to the new millennium styles.

“As someone who came of age in the Y2K era, I automatically cringe at a lot of the trends because some of my most embarrassing outfits happened during that time,” laughs Plewes. But here we are—poised to happily embrace that bedlam again. “Like any era of fashion that goes back roughly 20 years, there’s an automatic discourse,” she continues. “It inevitably comes back in style for a new generation.”

While you could hit up DePop or Poshmark for authentic vintage pieces, today’s designers are putting their own spin on their pieces, and we’ve put together a list of the top seven Y2K trends to shop today.

‘Painkiller’ on Netflix

Netflix’s new crime/drama mini-series 'Painkiller'

Stream ‘Painkiller’ on Netflix

Low-rise mini skirts

A model wearing a cream sweater and green skort, and a cargo mini skirt with camo print. — Credit: Reviewed / Reformation / Abercrombie & Fitch

The Y2K era certainly leaned into the concept of “mini” when it came to skirts, with hems climbing up as high as you would dare and waistlines hitting well below the true waist. Employing an “opposites attract” concept to pairing pieces, Plewes suggests wearing today’s low-rise minis with oversized menswear-inspired button-up shirts worn open with a tank or tee under to balance out the barely-there nature of the skirt.

The Imogen Skort from Reformation is 100 percent lightweight Tencel fabric and built-in shorts without giving too much away in terms of length. For a bolder take, Abercrombie’s 2000s Utility Micro Mini Skirt mixes the recent cargo trend resurgence with elevated front and rear cargo pockets and an early aughts-inspired length.

Shop the Imogen Skort in women’s sizes 0 to 12 in two colors, and Abercrombie’s 2000s Utility Micro Mini Skirt in women’s sizes XXS to XXL in five colors.

Low-rise flare jeans

Probably one of the most iconic Y2K trends, low-rise jeans were everywhere. What they lacked in rise was made up for with flared bottoms. “I would pair [low-rise flare pants] with a fitted or cropped tee and an oversized blazer or jacket with loafers,” says Plewes when taking this era trend into modern day.

The American Eagle Next Level Super Low-Rise Flare Jean channels retro vibes with a super-low rise, slim leg, and just the right amount of flare in super soft and stretchy denim. The Angeline by AG Jeans is a low-rise flare jean featuring a light, faded wash with lived-in details and worn hems. The 360° Denim with vintage bi-stretch construction is flattering and comfortable.

Shop the AE Next Level Super Low-Rise Flare Jean in women’s sizes 00 to 20 in short, regular, and long, and Angeline by AG Jeans in women’s sizes 24 to 32.

Slip dress

Our love affair with slip dresses continues. “I loved and still love the chiffon bias cut spaghetti strap style dress that was so big during that time,” says Plewes. To make the piece look more substantial than an undergarment, it’s important to style a slip dress just the right way. “Pair with a sneaker like an Adidas Samba or the Asics Gel-Nimbus 9,” she continues.

A timeless classic for good reason, the slinky Satin Midi Slip Dress by Vince is cut from rumpled satin. The scoop neck and adjustable straps make it a soft addition to your closet. Not to be outdone, the 100 percent silk Kailyn Dress from Reformation is also one sexy slip, with barely-there adjustable spaghetti straps and a beautiful fitted bodice. The scoop neckline and relaxed skirt balance out the look.

Shop Vince Satin Midi Slip Dress in women’s sizes XS to XL in two colors, and Reformation Kailyn Silk Dress in women’s sizes 0 to 12.

Tracksuits

Nothing screams Y2K louder than a snapshot of Paris Hilton sporting a bedazzled “Juicy Couture” logo on her track pants' derriere. And if you’re coveting a blinged-out velour two-piece, you aren’t the only one. According to the company, sales of new Juicy Couture pieces increased 137 percent from January to May 2022 compared to the same period the previous year.

The Hollywood Snap Pocket Cotton Velour Track Pants and Classic Hoodie from Juicy Couture remain classic without the extra bling. From the Icons collection, the original classic jacket brings Y2K nostalgia with the iconic rhinestone "J" zipper pull, while the track pants are signature low-rise.

For a less fitted, more modern take on the tracksuit, Pítusa’s two-piece Inca Pullover and Trackie Pants Set is crafted in luxurious and super soft pima cotton. Their effortless, relaxed fit makes the set a comfy choice when paired with slides or sneakers.

Shop the Juicy Couture Hollywood Snap Pocket Cotton Velour Track Pants and Classic Cotton Velour Hoodie in women’s sizes XS to 3X in two colors, and the pítusa’s two-piece Trackie Set in women’s petite and standard sizes in seven colors.

Denim on Denim

Models wearing a denim maxi skirt and mini dress. — Credit: Reviewed / Topshop / Collusion

Never has a trend been more polarizing than the denim-on-denim “Canadian tuxedo” immortalized by Britney Spears and Justin Timberlake in 2001. While this over-the-top look isn’t for everyone, head-to-toe denim has returned.

Doubling up with the low-rise trend, Topshop’s Denim Low Rise Y2K Maxi Skirt offers up non-stretch cotton in a pillar of denim. Wear a denim shirt in the same mid-blue wash, with just a hint of a white tank peeking out to break up the monochromatic look. Or keep your all-over denim simple with the Collusion Y2K Denim Mini Halter Neck Dress. Exclusive to Asos, the dark-blue washed non-stretch denim is 100 percent cotton, and the open back adds a sexy touch. Pair with high tops for a sporty look or cowboy boots for a Western vibe.

Shop Topshop’s denim low rise y2k maxi skirt in women’s sizes 0 to 14, and the Collusion Y2K denim mini halterneck dress in women’s sizes 0 to 14.

Short Strap Shoulder Bags

Give that belt bag a break and instead reach for a short strap shoulder bag, a constant accompaniment in the ‘00s—when we were in the middle of the “it” bag phenomenon.

Baggallini’s Modern Pocket Half Moon Bag allows you to customize your comfort with an adjustable, removable crossbody strap and removable shoulder strap, along with a grab-and-go phone pocket, plenty of interior compartments, and a convenient lipstick loop.

Aldo offers up its own stylish pop of color to complement your outfit with the intricately woven Emrys bag. The braided detailing gives an extra splash, while the roomy main compartment keeps everything at your fingertips.

Ribbed Cardigans

Whether you toss it over a slip dress for a little extra warmth, or pair it with a matching ribbed tank in a colorful set, the ribbed cardigan is returning to plenty of fanfare as a classic way to look polished and on trend.

From the Nordstrom exclusive brand BP., the close-fitting Crop Rib Cardigan is knit in sustainably sourced materials for a shorter silhouette with soft all-over ribbing. For an unforgettable matching set, the Anya Fitted Rib Cardigan Sweater by The Drop fits snuggly to the body in a ribbed style and can be paired with the matching ribbed Roni V-Neck Cropped Sweater Tank underneath.

Shop the Crop Rib Cardigan by BP in women’s sizes XXS to XL in four colors, and The Drop Anya Fitted Rib Cardigan Sweater and Tank in women’s sizes XXS to 5X in seven colors.