Cover Up in Y2K Style in a Juniors’ SO® Cable-Knit Cropped Button-Front Cardigan

A cardigan sweater is a key component to any closet that’s filled with Y2K-inspired style. It’s perfect for that layered look that was so common in the late ’90s/early ’00s. This cardigan from SO fits into the trend perfectly with its ribbed detailing and button front.

To achieve that ideal layered Y2K look, add a halter top and a pleated skirt, or a crop top with wide-leg jeans. This will provide a turn-of-the-millennium vibe that’s also laid back and versatile.

Let Your Retro Style Flow in a Juniors’ SO® Sleeveless Cinched Front-Slit Midi Dress

Worn under your cardigan, a midi dress easily and effortlessly ties into the Y2K trend. With a side slit and cinched details, this juniors’ dress from SO provides timeless charm, too, meaning it looks great in any modern wardrobe as well.

The sleeveless design makes it perfect to cover with a sweater or shawl. The midi length hits between the knee and ankle, providing the perfect length to wear for any occasion.

Step into a Trendy Time Machine in madden girl Hollyy Women’s Mary Jane Shoes

The right pair of shoes can go a long way in achieving the Y2K look. These Mary Jane shoes from madden girl provide the throwback appeal for this trend, but also provide modern appeal that allows them into your current collection, too.

The chunky sole found on these shoes is a hallmark of the Y2K theme. The buckle accent on the upper also ties into the theme. The rubber outsole is durable and offers plenty of traction as well.

Finish Off Your Look with Women’s GOLDTOE® 3-Pack Trouser Dress Socks

Comfortable socks are a must for any outfit, and these GOLDTOE dress socks give you the essentials needed to complete the cardigan look.

The reinforced, comfort toe seam is what GOLDTOE is known for. The trouser length hits just below the knee, offering complete coverage. Three pairs are included in the pack, giving you plenty to add to your everyday wardrobe.

Reach into the Wayback Machine with a Girls SO® Ribbed Collar Polo

A simple, straightforward polo shirt is timeless as is. But it really shines as part of a throwback Y2K outfit. This ribbed collar polo connects to the looks popular in the late ’90s, and is super versatile.

The stretchy fabric ensures comfortable wear with any other outfit essentials. Its short sleeves make it perfect for wear in basically any season. A polo is also perfect to pair with anything from shorts to skirts.

Expand Your On-Trend Clothing Collection with Juniors’ SO® Swirled Wide-Leg Jeans

Nothing embraces the late-’90s vibe like wide-leg jeans. These jeans from SO are Y2K compliant, as they provide the iconic silhouette that this era is known for.

A traditional five-pocket design offers timeless appeal. The fun swirled print on the jeans offers a more unique look that’s sure to conjure up retro feels.

Elevate Your Y2K Style with Women’s Converse Chuck Taylor All Star Lift High Top Shoes

Converse Chuck Taylor All Stars have been a fashion staple for many years, keeping their appeal through many different trends and changing fashion tastes. This is true with the Y2K theme as well, as these high-top Chucks are a must for any of these looks.

A canvas upper provides flexibility and breathability, while a padded footbed cushions every step. The reinforced rubber front protects your toes, and the sturdy rubber outsole promises superior traction.

Top Off Your Look with a Women’s LC Lauren Conrad Navy Floral Top Knot Headband

Hair accessories are popular additions to Y2K-inspired outfits. This women’s LC Lauren Conrad headband connects to the retro look, while adding in some modern appeal as well.

The top knot detail offers feminine flair. The floral pattern ensures the headband always remains on trend. The flexible design means the headband is a one-size-fits-most option.

You’ll Look Good as Gold in a LC Lauren Conrad Set of 3 Pull-Tie Bracelets

Another accessory option to consider as part of your Y2K outfit is jewelry, and these LC Lauren Conrad pull-tie bracelets are sure to become instant favorites.

The gold-tone, polished finish offers a luxurious look. The pull-tie design ensures the proper fit. And with three bracelets included, you can mix and match the set with other pieces to create a personalized look.

Find Balance in Your Wardrobe with a Juniors’ Yin-Yang Cropped Embroidered Tee

Combining cropped tops and baggy jeans creates a look that’s straight from the turn of the century. This juniors’ T-shirt fits the theme to a “tee,” as it offers a cropped fit that’s a trademark of late 20th century style.

The tee also features a yin-yang graphic, as well as embroidered detailing at the neckline, cuffs and hem.

Make Room in Your Closet for Juniors’ SO® Super High-Rise Baggy Dad Jeans

Baggy jeans are an icon of late-’90s/early-2000s fashion. So if you’re looking to achieve the Y2K trend, you need to have a pair of them in your wardrobe.

These juniors’ jeans from SO offer a superhigh rise to go along with their relaxed fit and wide-leg style. The four-pocket design provides a classic look, and the stretch denim construction ensures all-day comfort.

Slide Into Throwback Style with Vans® Asher Platform Women’s Slip-On Shoes

A pair of Vans shoes is also a must when going for a retro Y2K outfit. Slide-on Vans, like these Asher platform shoes, check all the boxes for footwear needed to achieve this on-trend look.

The slip-on design makes putting the shoes on or taking them off a breeze. A double-stitched upper ensures long-lasting durability. The iconic Vans vulcanized outsole provides grip and traction.

Put a Lid on Your Look with a Women’s Sonoma Goods For Life® Printed Cord Bucket Hat

To complete your cropped and baggy Y2K outfit, add in a bucket hat from Sonoma Goods For Life. Not only does the hat offer appeal straight from the ‘90s, but it also works to keep the sun off your skin.

The wide brim adds signature bucket hat style. The elastic inner-band closure provides the perfect fit for all-day wear. A timeless plaid pattern ties into the Y2K look as well.

Keep Warm in a Juniors’ SO® Balloon Sleeve Crewneck Sweater

The Y2K trend can be achieved in any season, and the cooler times of the year are no exception. This juniors’ SO crewneck sweater is perfect for fall or winter, when sweater weather is the norm.

The soft cotton blend keeps you warm and feeling your best. The drop-shoulder styling and ribbed hemline enhance the look.

Complete Your Cool-Weather Look with Women’s LC Lauren Conrad Raw-Hem High-Waisted Skinny Ankle Jeans

The Y2K trend isn’t all about the baggy look when it comes to denim. These LC Lauren Conrad skinny jeans are classic, and fit into throwback trends, as well as modern looks.

The skinny-leg opening and high-waist design provide everyday appeal. The raw-edged hems enhance the look, and the traditional five-pocket detailing ensures the jeans are always on trend.

Kick Back and Relax in a Juniors’ SO® Oversized Weekend Tunic Top

Oversized tops are popular in the Y2K trend, and this tunic from SO is sure to be a frequent pick when you’re embracing the style.

The drop-shoulder silhouette and long sleeves provide a signature appeal. A vented hem allows ease of movement. The oversized fit ties into the Y2K trend. A soft French terry construction keeps you comfortable.

Go Full Grunge with a Juniors’ SO® Pleated High-Rise Mini Skirt

A plaid pattern is key for any outfit that’s connecting to the ’90s grunge look. This SO skirt features that signature print, making it a must for the Y2K theme.

The pleated detailing enhances the throwback appeal of the skirt. The twill construction provides durability and comfort. The miniskirt length is designed to hit mid-thigh. The zipper closure makes dressing a breeze.

March Back in Time in a Pair of madden girl Carra Women’s Platform Combat Boots

Platform shoes are a Y2K staple. Combine the platform sole with a combat boot silhouette, and you’ve got a pair of kicks that perfectly capture the throwback appeal.

These madden girl combat boots provide the style you want for your Y2K outfit. The platform sole is sturdy and durable. A side-entry zipper ensures easy on and off. The padded footbed provides cushioning with each and every step.

Head Outside in Warmth in a Women’s Lands’ End CashTouch Winter Beanie Hat

The last thing you need to top off your grunge look is a beanie hat. This option from Lands’ End not only fits the theme, but also offers much in the way of keeping you warm.

The cashmere-like CashTouch construction provides a soft feel and plenty of warmth. Several color options allow you to choose the one that works best for your Y2K wardrobe.

Look Like a Winner in a Women’s Champion® Crop Tee

Cropped tees have already been discussed as being a Y2K trend essential. This crop tee from Champion provides a sporty appeal that connects to a more athletic Y2K look.

The soft jersey construction keeps you cool and comfortable as you move throughout the day. The relaxed, cropped fit is on trend and offers feel-good wear.

You’ll Have it Made in the Shade in Ray-Ban RB3025 Original Aviator 58mm Sunglasses

A pair of sunglasses is a great addition to any wardrobe, and the Y2K trend is no different. Ray-Ban sunglasses are always in style, and these Original Aviators are classic.

The metal frames and glass lenses ensure durability. The sunglasses come with a pouch for simple and easy storage when not in use.

Keep Warm in a Women’s Champion® Powerblend Fleece Boyfriend Sweatshirt

You’ve already added a Champion tee to your sporty Y2K look, so be sure to layer up in a coordinating Champion sweatshirt as well.

This women’s Champion Powerblend boyfriend sweatshirt offers a cozy fleece construction that provides unmatched comfort and warmth. The iconic “Champion” mark across the chest ensures a signature style that’s always on trend.

Pick Up the Pace in a Pair of Women’s Champion® Powerblend Fleece Joggers

Another item from Champion that fits easily into your Y2K wardrobe is a pair of joggers. Their laid-back look and maximum comfort make them perfect for everyday casual wear.

The warm, comfortable fleece construction feels great as you move. The material is made to reduce shrinking and pilling, ensuring long-term wear. Two convenient front pockets provide storage for your phone or keys. Lastly, the ribbed waistband and cuffs provide the perfect fit and silhouette.

Embrace the Athletic Look in FLX Excel Women’s Shoes

No active outfit is complete without a sporty pair of shoes. These women’s FLX Excel shoes are perfect for any on-the-move wardrobe, including the throwback Y2K trend. 

The lace-up closure makes them look classic in any outfit. The flexible upper lets you move with ease. The supportive footbed and traction sole helps you maintain balance and cushions your feet with each step.

Find Some Fun Fashion in a Juniors’ SO® Cropped Contrast Seam Top

The Barbiecore look is all about connecting to aesthetics presented by the popular doll, Barbie. The theme taps into the Y2K look, too, making the trends natural companions in the world of style.

Crop tees are a familiar part of Y2K looks, and Barbiecore fashion incorporates them, too. This juniors’ cropped top offers an asymmetrical hemline, ribbed detailing and contrast trim to enhance the look. Layer the crop top with a cardigan sweater for added appeal.

Incorporate Iconic Style with Juniors’ SO® High-Rise Pull-On Flare Pants

Barbie is known for her signature looks, and these juniors’ SO flare pants provide your own slice of timeless fashion appeal.

The checkerboard pattern is timeless and works well with other Y2K trend items. The wide, flared legs also work in your wayback wardrobe. The high rise and elastic waistband provide the perfect silhouette and fit.

Tie Your School Day Look to the Y2K Trend with a Juniors’ SO® Lace-Up Plaid Mini Skort

As you head back to school at the start of the year, you want to make sure you look your best and embrace the most popular trends out there. This mini skort from SO is great for anyone looking to bring the Y2K look into the classroom this year.

An asymmetrical hemline and twill construction provide signature style that’s key for the Y2K theme. The skort design offers versatility. A hidden elastic waistband with side-tie detailing enhances the look, and provides the perfect fit and ultimate comfort.

Take Your Back-to-School Look to New Heights in a Juniors’ Small Butterfly Cropped Embroidered Tee

It should come as no surprise that a cropped tee would find its way into your back-to-school Y2K look. This tee is charming and on trend, and comes complete with embroidered detailing at the neckline, cuffs and hem.

Add in a Layer for those Chilly School Days with a Women’s Levi’s® Original Trucker Jean Jacket

When getting ready for class in the morning, you’ll always want to be aware of the weather. Fall days can be pretty chilly, so a top layer is a must. This women’s Levi’s jean jacket rises to the occasion, providing warmth and style.

The timeless denim construction makes the jacket a versatile, everyday selection. The jacket is lightweight enough to wear easily, but substantial enough to offer a top layer of warmth that’s a must in the autumn months.

Make a Throwback Statement in madden girl Everett Women’s Wedge Sandals

You can take the basic Y2K theme and incorporate other trends into it, too. These women’s wedge sandals from madden girl not only work with the Y2K style, but also bring in some edgy appeal to your look.

Dual straps with pyramid stud details provide an ideal fit, all while offering standout style. The padded footbed on the platform sole cushions your steps.