9 Ways to Wear a Dress With Leggings & Capture Y2K Nostalgia

Take a Y2K fashion tip with all of these accessories, fabrics, and dresses to wear with leggings. Create tons of stylish looks with these ideas.

Updated January 4, 2024

From the plethora of oversized cargos and scallop-edged sheer shirts we've found, it's safe to say that Y2K is back. Get ahead of the curve by learning how to wear a dress with leggings in a stylish way so that no one will mistake you for a late-00s Disney Channel star.

Leggings Pair Well With Mini to Calf-Length Dresses


We've all gotten carried away with one or two seasonal clearance clothing hauls. But dresses, unlike separates, take a little more finessing. Having a wardrobe full of dresses can cut down on decision-making, but wearing the same silhouette every day can get boring.

Liven things up by adding some leggings underneath your dresses. The best ones to pull out of the closet are any on the mini to calf-length spectrum. While you can pair leggings with a maxi dress for extra warmth, the hidden layers won't add much to your outfit.

Stiffer Fabrics Keep Dresses From Clinging to Leggings


Dresses with a lot of drape and cut on the bias are designed to cling to your body. They use your natural shape to add structure. Yet, leggings — with their own textures, pockets, seams, and waistbands, can disrupt this visual flow.

So, if you want a cohesive and smooth shape, stick with dresses that are made of stiffer fabrics. Usually they feel thicker, have some heft to them, and don't have much draping.

Stick With Flat Waistbands for a Smooth Look


Like seamless underwear was revolutionary for people who don't find thongs comfortable, seamless waistbands are tailor-made for putting under dresses. The hack to keeping your waistbands from cutting an unflattering line under your dresses is to look for leggings that don’t have a sewn edge right at the waistband. Often, these come sewn over elastic cords, which can add further bulk.

Instead, look for leggings with their final seams towards the hips. These "seamless" leggings give you a flat piece of fabric from your waist to hip which won't poke out under a dress.

The Warmer the Season, the Shorter the Leggings


When people think about wearing leggings under dresses, thick woolen leggings and winter holiday frocks come to mind. But you can put a pair of leggings under a sun dress in the middle of spring, too! It all comes down to the type of leggings you choose.

Go for thinner calf-length leggings in summertime, and thicker, ankle length ones in winter. This lets you style your outfits in a way you love without overheating or freezing.

Decorative Edges Will Complement a Sophisticated Dress


If you were a teen in the late 2000s and early 2010s, then you know these calf-length lacy-edged leggings well. Every young celebrity and pop star wore them on the daytime red carpet, and there's nothing stopping you from wearing them, too.

A plain legging will do the job, but sometimes you want something with a little more pizazz for an embellished dress. Look for leggings with lace inserts and frilly edges to complement those dressier pieces.

Leggings Give Everyone the Confidence to Rock a Mini Dress


One of the best things about wearing leggings under dresses is that they let everyone feel comfortable rocking a mini dress. Leggings come to the rescue no matter what your body type is and can help many of us feel a little more relaxed and confident in a shorter dress style. 

So, don't put that cute dress back just yet! All it needs is the perfect pair of leggings to go with it.

Asymmetrical Dresses Will Give You the Perfect Y2K Look


Listen, it might not feel like it's been long enough for Y2K trends to come back round, but they're back with a vengeance. Celebrate that iconic style that Disney stars of the day championed with an asymmetrical dress over a pair of leggings. The more jellyfish-like the edges are, the better.

Dresses With Side Slits Can Elongate Your Lines


If you've got a curvier frame and find it hard to find the perfect dress that fits both your top and bottom measurements, look no further than ones with side slits. Double slits won't only make you feel a little saucy but they'll also be incredibly comfortable. Throw on a pair of leggings in a contrasting color and your legs will look like they go on for miles.

Spice Up Your Look With Leggings Under a Sheer Dress


Leggings under dresses usually come off as sweet and charming, but sometimes you want to add a little allure to your outfit. Keep the combo and up the spice factor by picking out a sheer dress. From tulle to lace to tattered fringe, there’s a sheer dress for every kind of personal style. Get the ultimate peekaboo look and you can take your day leggings into the night.

Quick Tip

Sheer leggings can also provide a cool contrasting look when you're wearing a dress made of a thicker fabric, like a sweater dress. 

Dresses + Leggings Are a Winning Y2K-Inspired Combo


Bring that quirky Y2K red carpet fashion straight into the 2020s with your picture-perfect leggings and dresses looks. Whether you enjoy them because they keep you warm or you like to take the "more is more" approach to your outfits, leggings under dresses have been resurrected and they might be here to stay.

Trending on LoveToKnow
9 Ways to Wear a Dress With Leggings & Capture Y2K Nostalgia