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How to Wear the 90s Trend in the Dead of Winter

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Quick, what’s the iconic garment of 90s fashion? For me, it’s the crop top — showing off miles of midriff above a pair of baggy, light wash jeans. Funny thing is, that outfit, which represents an entire decade of fashion, is completely impractical when winter pulls temperatures below 65.

It’s exactly 9 degrees outside in Missouri today. And there’s no way a crop top makes it into my rotation anytime soon.

But if you’re really feeling the ’90s vibe, you probably don’t want to put things on hold for six months until the sun shines once more. And you don’t have to! Because I’m taking the best trends from the ’90s and winterizing them. Read on for four outfits to channel your inner Spice Girl even when it’s cold outside.

90s Outfits for Winter

As you can guess, layering is the key to staying warm in your ’90s gear. It’s tricky with ’90s wear though, because the popular silhouettes either show off your natural shape or completely cover it up. A slip dress, for example, puts your whole bod on display. But then the oversized jeans and flannel shirt combo hides you behind a mound of plaid and denim.

As a general rule, balance is your goal. Pair the boxy, loose garments with those that hug a little tighter or reveal a little more. Now, let’s get to the specifics.

1. Slip Dress and Blazer

When Kate Moss wore a sheer slip dress, she was surely in a temperature-controlled room. I’d likely get frostbite just walking to my car in a dress that flimsy.

To warm things up, pair your slip dress with a long, heavy blazer. The difference in texture between your light, airy dress and structured blazer makes for an interesting combo and a modern take on an old trend.

2. The Skater Skirt & Fleece Leggings

Maroon pleated mini skirt
ASOS Tailored Mini Pleated Skirt, $35, ASOS
Black Fleece Leggings from Target
Women’s Stretch Fleece Leggings, $15, Target

On “Friends,” Rachel Green wore her tartan skater skirt with knee-high socks, but that just seems silly for anyone over the age of 12. Instead, go for a pair of black, fleece leggings and ankle booties. You can and should also wear a long-sleeve sweater over the top.

3. Overalls and Cowl Neck

Thirty years ago, we called them overalls. Today you might prefer the phrase “denim jumper,” as it sounds less like something a car mechanic wears.

Whatever the name, they’re classically cute with t-shirts. You could add a bomber over the top, but I also like overalls paired with a thick cowl-neck sweater. Choose a sweater that’s more fitted than bulky and wear it underneath your jumper.

4. Baggy Jeans and Bodysuit

Check longline gray blazer
Check Longline Blazer in Grey, $68, Chicwish

Jeans in the ’90s were either high-waisted and kind of shapeless, or they were hip-hugging flares. Flares are easy to winterize: tuck in the long-sleeved shirt of your choice and add a blazer.

The baggy jean is more of a challenge because it lacks structure. There’s a reason everyone wore their jeans with crop tops after all. Mimic the crop top silhouette with a long-sleeve bodysuit that hugs your upper half. You can also add a calf-length blazer, which puts visual bookends on those roomy pants.

And that’s how you do ’90s fashion in the winter!

Need more 90s fashion inspiration? You’ll love these: