You know how they say fashion repeats itself? It’s 100 percent true. Younger generations haven’t lived through older trends, so each one feels brand-new. This time around, people want to dress like it’s 1999 again. The late 1990s and early 2000s are back, and we’re not mad about it.
Remember loose-leg pants, chunky sandals, bright colors and baby tees? Whether you still have any of these pieces in your closet or you’re trying Y2K fashion for the first time, here are some Y2K styles to inspire your wardrobe.
Off-the-Shoulder Crop Tops Are Super Wearable
Why you need it: Some Y2K fashion isn’t the most practical for daily wear. Halter tops with plunging necklines or ultra-short crop tops with ties that wrap around your waist are cute and all, but this one-shoulder, ribbed crop top is way more versatile. It comes in tons of colors, and you can layer it with a slouchy cardigan for more coverage.
Review: “Cute top. Exactly like the picture. Thick material, great red color and fits great. I got the S size. Very short top so most of your stomach will be showing, but that’s what I want it to do so I have no problem with that. Overall, it’s a cute top and goes perfect with my jeans.” — Ana Maria
Buy now: SheIn Women’s Plain One Shoulder Stretchy Ribbed Knit Crop Top, $13.99
How Cute Is This? Perfect With Mom Jeans
Why you need it: The majority of Y2K pants were either high rise or extremely low rise — so low that we couldn’t sit down for half a decade without risking indecent exposure charges. So far, high rise has made more of a comeback, and for that, we are eternally grateful. Full-length shirts with high-rise pants leave something to be desired, so try a baby tee instead.
This one is essentially a mini, ribbed polo shirt, and it looks great with a high-waisted mini skirt and a pair of chunky sneakers.
Review: “One of my favorite tops that I ever bought! The color is so pretty!” — Sarahstabile
Buy now: Stormi Polo Tee, $22.95
Ruching, Spaghetti Straps and Fuzzy Tops Are Back
Why you need it: Crop tops with pencil-thin straps are cute and comfy, especially when they’re fuzzy. This one is super soft, and the ruching is flattering on every figure. The tie at the bottom adds a nice touch. Pair this with a pair of high waisted jeans, or with a cute mini skirt and an oversized jean jacket.
Review: No reviews yet, but it has four five-star ratings!
Buy now: H&M Brushed Crop Top, $17.99
A Y2K Layering Piece Standard
Why you need it: This feels like something Rory Gilmore wore in “Gilmore Girls” at some point. Shoulder-bearing spaghetti strap tanks are cute, but what happens when it gets chilly?
The middle ground between wearing a regular T-shirt and putting on a sweater is this short cardigan. The ruffle trim and single button closure are very Y2K, as is the fine rib knit. It’s still short-sleeved, but it’s a nice extra layer for cool evenings.
Review: “Super cute and great for summer. Material is nice and soft.” — Anonymous Reviewer
Buy now: Ruffle-trimmed Ribbed Cardigan, $17.99
Two Words: Jean. Skirt.
Why you need it: No Y2K wardrobe is complete without at least one jean skirt. It’s fitted, but the material of this particular jean skirt is made from American Eagle’s stretchiest, softest denim. The skirt sits at your natural waist, and it’s a little longer in the back than the front for even coverage. Despite the stretch, the fabric supposedly never loses its shape.
Review: “This skirt fits perfectly. It is very comfortable. I love the length it was just right for the occasion. I truly recommend this skirt if you are looking to have fun with friends and family.” — Tamera
Buy now: AE Ne(x)t Level Curvy High-Waisted Denim Mini Skirt, $29.97
School-Girl Vibes Are on Point
Why you need it: The school-girl aesthetic doesn’t have to be preppy. We love how Free People styled this timeless Y2K skirt with a simple halter crop top, lace-up boots and a loose-fitting jacket.
The skirt pleats are defined to add dimension, and the golden plaid pattern is grownup enough to not resemble a school uniform.
Review: “This skirt was so soft and fit exactly true to size. Breathable enough for summer but definitely could work for a fall/winter outfit, too.” — Jmcampbell
Buy now: Free People Honey Pleated Skirt, $60.00
Leather Mini Skirt? Yes, Please!
Why you need it: Edgy and bold are the words that come to mind with this vegan leather mini skirt. It’s soft and form-fitting, but the silhouette is slightly flared so it’s more comfortable to move in than a pencil skirt. The back has an exposed silver zipper to take the sexiness level up a notch.
You know the hottest thing about it, though? It has pockets.
Review: “Snug fit perfect with a bodysuit. The pockets are amazing I have a few other skirts from Lulus without pockets, but this one really is great.” — Jessica G.
Buy now: Lulu’s Harley Black Vegan Leather Mini Skirt, $48
You Could Totally Wear This to Work
Why you need it: Most Y2K styles aren’t work-appropriate, but this one could make the cut depending on where you work. We love the bright orange color, and the floral pattern adds to the fun.
The ruching and ruffled hem are the most Y2K elements of the ensemble, but we love them. All in all, this skirt is a great throwback without going over the top.
Review: “This skirt is adorable! It’s super flattering and comfortable and not too short, which tends to happen with my height. Can’t wait to wear this out!” — Kjahly26
Buy now: Free People Romi Mesh Mini Skirt, $50
This Y2K Style Is Like a Dress, Minus the Middle
Why you need it: We could ask why this wasn’t just a one-piece dress, but this actually looks a lot better. Sweater dresses usually seem heavy. This tight-knit, ribbed crop top and skirt set still feels light and airy enough for warm weather.
The pastel shade amplifies the Y2K vibes. Plus, the whole outfit is stretchy, and the reviews are almost unanimously amazing.
Review: “I had been waiting for this set to restock in my size for months, and when it finally did, I ordered it IMMEDIATELY. I was NOT disappointed! In the words of a friend, it is ‘the most flattering thing I’ve ever seen you in.’ It’s comfy and fits perfectly.” — camstack
Buy now: 90’s Babe Sweater Set, $60.00
Slip Dresses for That Effortlessly Beautiful Look
Why you need it: Slip dresses are Y2K fashion staples, and we love this one for so many reasons. Its knee length is modest enough for work, and the entire dress is cut on the bias, so the way it drapes is super flattering.
The rich navy color is stunning, and the Mulberry silk satin is both gorgeous and washable. It looks dressy in the picture, but it’s so comfortable that you’ll be tempted to wear it every week.
Review: “Loooove!!!! Literally amazing! Fits like a DREAM! Buy it now??????” — Jennifer C.
Buy now: Quince 100% Washable Silk Slip Dress, $74.90
Another Slip Dress With a Million Rave Reviews
Why you need it: Here’s another variation of the silk slip dress that we adore. Again, it’s cut on the bias for a flattering silhouette, and the slits on the side are a nice touch. This is one of those dresses that’s both comfortable and flattering, and it’s really hard not to love it.
It comes in four colors, but Anthropologie has made the same dress in other colors before. If you don’t see one you like, come back in a month or two, and they might have more options.
Review: “This dress is the embodiment of the sentiment that you have and are everything you need. It’s sexy and fun and bright. The cut is flattering, the fabric texture and flow are cute and bounce a little if you’re curvy. Amazing dress, fun pattern, great quality. Wore to a breakup. Worth the hand-washing.” — Suzysuzysuzy
Buy now: Elyse Bias Slip Dress, $120
A Flattering Bodycon Dress to Keep You Cool
Why you need it: Shift dresses of all kinds are in. Y2K fashion often features spaghetti straps that tie at the shoulders, and this dress does it right. The square neck looks great on any body type, and the Dalmatian print is adorable. Add some accessories, and you’re ready for the weekend.
Review: No reviews yet!
Buy now: Pretty Little Things Black Dalmatian Print Tie Strap Shift Dress, $25.00
Wide-Leg Jeans That You’ll Want to Wear Daily
Why you need it: Kiss your skinny jeans goodbye. They had a good run, but they are so last year. Oversized jeans have replaced them, and they are better in almost every way. They’re so much more comfortable!
This high-waisted version is loose through the hip and thigh, so you won’t have to hold your breath every time you sit down. Feel free to live in these because the light-wash denim gets softer with every wash.
Review: “They’re super flattering on the butt; the midrise is everything. Best pair of jeans I’ve bought in a while, highly recommend!” — Giovanna S
Buy now: Aritzia Go Off Road Dad Jean, $60
You Can’t Wear the Same Pair of Jeans All the Time
Why you need it: When the last pair we mentioned is in the wash, try this one on for size. Levi’s are known for lasting forever, so you’ll get years out of these jeans.
The straight-leg style is on-trend, and it’s easy to mix and match for the full Y2K look. Add a cute baby tee or a light, button-front cardigan, some platform sandals and toss your hair up with a scrunchy. Done.
Review: “Such an iconic jean that sits exactly above the belly button right at the ribs (hence the name). They make my bum look so good, and they will be a staple in my wardrobe! I assume they’ll stretch with wear, so I recommend getting your normal size and as well as checking the Levi’s size chart for accurate sizing.” — Leira22
Buy now: Levi’s Ribcage Ultra High-Rise Straight Jeans, $108
Speaking of Denim…
Why you need it: Jean jackets are back, too, particularly light-wash ones. This oversized denim jacket is oversized and distressed (how relatable!), and it has convenient side pockets to throw your phone or keys in.
Denim tends to be stiff, so the looser fit is welcome. This is a great piece to throw over a mini dress with your favorite pair of Doc Martins.
Review: “I’ve been looking for a cropped denim jacket for a while, and this one is amazing! It has distressing on the wrist area, upper back, behind the neck, it is so cute. I do recommend sizing one size down because it does feel oversized. Even the small I purchased is pretty big!” — Giana N.
Buy now: AE Cropped Destroyed Denim Jacket, $59.95
We Hope You Didn’t Toss Out Your Juicy Tracksuit
Why you need it: Seriously, if you still have a Juicy tracksuit, put it back in rotation. Matching velour track suits are a Y2K fashion hit. You can still buy the Juicy version, but this set by Sean John is way less expensive and just as cute.
Review: No reviews yet!
Buy now: Sean john x missguided navy velour wide leg pants, $19.00
Blocky Heels for a Night Out
Why you need it: These Calvin Klein heels aren’t cheap, but they’re worth the splurge. They’re made with a small, 2.16-inch heel and a square toe that’s both comfortable and trendy. The crocodile print and thin straps add to the Y2K feel. Wear them to work or to brunch. They go with everything. So chic.
Review: “The heel height is good, especially with the chunky heel. I like the crossover of the strap, which keeps your foot from sliding in the shoe. The quality and comfort is great as well.” — Patsy
Buy now: Calvin Klein Women’s Becca Slip-On Strappy Dress Sandals, $99.00
Chunky Sneakers Go With Virtually Everything
Why you need it: Canvas high tops have rarely been out of style, but the heavy soles on these make them extra Y2K-esque. There’s nothing like a crisp, white pair of classic Chuck Taylors to complete a casual outfit. Plus, the modern Ortholite insoles are way comfier than they were back in the day.
Review: “I NEVER write reviews but I had to. I got these shoes a year ago, and I wear them every single day. THEY ARE THE BEST SHOES IN THE WORLD. They are comfortable, too. I absolutely think you should get them!!! Plus, they go with almost anything.” — lomaster
Buy now: Converse Chuck Taylor All Star Lugged High Top Sneaker, $70.00
Who Could Forget This Iconic Y2K Sandal?
Why you need it: This pair of shoes is possibly the most Y2K item on this list. Everyone had these circa 2001. The soles don’t have the best traction, but the stretchy upper part feels great and keeps your foot from slipping out of them. They’re just as easy to slip into. If you find yourself stepping into them every time you leave the house, we won’t be surprised.
Review: “I had shoes just like these when I was a kid! So ’90s. For chunky shoes, they are pretty lightweight. I usually wear a 7.5 and got an 8 since reviews said to size up — they fit perfectly.” — sof
Buy now: Steve Madden Women’s Slinky30 Wedge Sandal, $79.00
Y2K Fashion Tip: Pair Bright Colors With Denim
Why you need it: Buckles and neon are definitely acquired tastes, but the bright orange of these rubbery sandals is so fun. The shoe itself is comfortable and lightweight, and the thick sole is totally Y2K. They’re great for pretty much any casual occasion and comfy enough to walk in for hours. Wear them with jeans, white linen pants or your favorite mini dress.
Helpful hint: The straps don’t have much give, so size up if you have wide feet or are in between sizes.
Review: “I was just looking for a fashionable wedge slip-on when I found this [one]. I fell in love with the yellow color. It is comfortable. The buckle is not my thing, but that’s OK. It’s cute. Love it!” — joy
Buy now: MACKIN J 591-1 Women’s Open Toe Platform Slide Sandals, $38.99
Don’t Forget Accessories!
Why you need it: You can’t leave the house without a bag, and this one exudes some serious retro energy. There are tons of ’90s style purses out there, so we picked one in black that will go with virtually anything you wear.
It comes with a convenient shoulder strap, and it zips up to keep your phone and wallet nice and secure.
Review: “New favorite bag. Good size and waterproof. Fits a lot of stuff, including my phone, keys, mini hair brush, purse and umbrella. Very happy :)” — Verified Purchaser
Buy now: Asos Design nylon curved 90s shoulder bag in black, $23.00
Seed Bead Necklaces Are Back
Why you need it: Everyone had these in the early 2000s. They’re an ideal accessory for those who want to add a touch of Y2K without revamping their entire closet.
This seed bead necklace set includes tons of bright, cheerful colors, and each one is made by hand. Wear these to the beach or on vacation for a pop of color and retro style.
Review: “I love these chokers so much! I like layering them with other gold or silver necklaces, or other beaded ones! And I can adjust the lenght so I can use them as chokers or as necklaces! ME ENCANTAN!” — Ingrid Cuthbert B
Buy now: Gysong Beaded Choker Necklaces For Women, $12.98
To Add A Little Edge to Those Mom Jeans
Why you need it: Y2K belts are tricky. Heavy, studded belts are a thing, but you don’t have to go that far to follow the trend. This metal belt is adjustable, stylish and unobtrusive, and it looks fantastic on any pair of jeans — very vintage. Each ring is about an inch and a half in width, so they’re small enough to fit through most belt loops.
Review: “Super cool! The rings were able to fit through majority of my shorts and jeans ! Very great quality, too!” — Anonymous Reviewer
Buy now: H&M Metal Belt, $17.99
For Sunglasses, There’s an Important Rule to Follow
Why you need it: Y2K fashion stipulates that sunglasses must either have thick frames or none whatsoever. There’s really nothing in between. These chunky glasses come in fun colors, and they’re cheap enough that you won’t feel too bad when you inevitably misplace them. For a day at the beach, they’re total must-haves.
Review: “They are thick, so they won’t break easily. Just be careful if you have a wider face, they are very solid. Overall beautiful and really block out the sunlight!” — Toffy
Buy now: Urban Outfitters Fairfax Chunky Rectangle Sunglasses, $16.00
Metallic Scrunchies Add a Pop of Color
Why you need it: Metallics seem like more of an ’80s thing, but scrunchies are eternal. This pack of 24 includes multiple fun colors, and there are enough that you can give away a few to friends who need to up their scrunchie game. The elastic bands are pretty durable, too, so each one should last a while before they lose their hold.
Review: “I love them! My scrunchy collection is insane right now, but no regrets.” — Lauren Hallisey
Buy now: Miuance 24 Pack 8 Colors Hair Scrunchies, $7.99
A Y2K Fashion Piece That Everyone Can Wear
Why you need it: If you can only get one piece of Y2K fashion, this is it. The bucket hat. Bucket hats can be as subdued or silly as you want. There are bucket hats with daisies, hearts, pandas and rainbows. There are plain bucket hats. There are frayed denim bucket hats. The options are endless.
This one comes in 21 different colors and helps protect your face from harmful UV rays. There’s also a version with frayed edges that we can’t get enough of.
Review: “The denim bucket hat was just what I was looking for. But, once my granddaughter spotted it … it became hers. She loves hats and this looked so cute on her I could not say no. I will be ordering another one for myself.” — Doris C.
Buy now: Chok.lids Everyday Cotton Style Bucket Hat, $13.99
