When you think of 90s fashion, what comes to mind? For me, it’s the classic crop top paired with baggy, light-wash jeans. It’s a look that defined an era, but let’s be honest—it’s not exactly practical when temperatures drop below 65 degrees.
Right now, it’s a freezing 9 degrees in Missouri, so a crop top isn’t making it into my wardrobe anytime soon. But if you’re loving the 90s aesthetic, you don’t have to wait six months for warmer weather. The good news? You can still rock your favorite 90s trends by giving them a winter-friendly twist. Here are four outfit ideas to help you channel your inner Spice Girl while staying warm.
The key to making 90s fashion work in winter is layering. The challenge is that 90s styles tend to either highlight your figure or completely hide it. A slip dress, for example, is sleek and form-fitting, while oversized jeans and flannel shirts create a more relaxed, covered-up look.
The trick is to find balance—pair loose, boxy pieces with more fitted ones to create a flattering silhouette. Now, let’s get into the details.
Kate Moss may have rocked a sheer slip dress in a perfectly climate-controlled setting, but in real life, that’s a recipe for frostbite. To make it winter-ready, layer your slip dress with a long, structured blazer. The contrast between the delicate fabric of the dress and the heavier blazer adds depth to your outfit while keeping you warm.
Rachel Green from *Friends* made the tartan skater skirt and knee-high socks look iconic, but for anyone over 12, that combo isn’t the most practical. Instead, swap the socks for black fleece leggings and ankle boots. Complete the look with a cozy long-sleeve sweater for extra warmth.
Back in the day, we called them overalls—now, “denim jumper” sounds a little more stylish. No matter what you call them, they’re a timeless piece that pairs effortlessly with a t-shirt. For a winter-ready version, layer a fitted cowl-neck sweater underneath instead. If you want extra warmth, throw on a bomber jacket.
90s jeans came in two main styles: high-waisted and loose or hip-hugging flares. Flares are easy to winterize—just tuck in a long-sleeve top and add a blazer. Baggy jeans, on the other hand, can be trickier since they lack structure. That’s why they were often paired with crop tops. To get a similar effect without freezing, opt for a fitted long-sleeve bodysuit to balance out the volume. A calf-length blazer adds a polished touch while keeping the look cohesive.
And there you have it—90s fashion, but winter-ready!