10 Retro-Chic Denim Skirt Outfits That Channel ’90s Nostalgia

The signs have been there for a while: The continued affinity for ’90s clothing, the rise of longer skirt lengths, confusion about which denim shape will become the next “it” style, etc. So we weren’t surprised when long denim skirt outfits began popping up everywhere. The revival of this throwback trend was inevitable, and after spotting long denim skirts in the hottest collections, with celebrities like Camila Mendes showing off hers straight from the Coach runway on Instagram, we knew it was time to invest in our own.

Thankfully, there are several options, including cute picks from H&M, Reformation, and Mango. However, if you’re less concerned about shopping and more interested in how to put together long denim skirt outfits, there’s plenty of that available, too. Fashionistas have been wearing this statement piece for months, proving it’s more versatile than we once thought. While denim often comes across as casual, jean skirts can be dressed up with heels or corset tops, turning this classic maxi into something super 𝑠e𝑥y.

A long jean skirt outfit at Coach’s Fall 2023 fashion show.

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Ahead, we’ve rounded up 10 long denim skirt outfits to try ASAP.

With a White Tee

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Denim and a white tee continue to be a timeless combination, no matter what kind of denim you wear. While the look always feels fresh, if you’re hoping to spice up your basic long denim skirt outfit, give things a fashion-forward twist by adding a belt and slouchy boots.

With a Leather Jacket

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Although a denim skirt is eye-catching on its own, the leather jacket acts as the statement piece in this case. Keep things casual by rocking a T-shirt underneath, or use the layer to balance out a bold, embellished top.

With a Bomber or Windbreaker Jacket

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If your personal style is more throw-on-and-go, style your long denim skirt outfit with a comfortable bomber or lightweight windbreaker jacket. Paired with chunky boots, you’ll definitely nail the ’90s vibe — in a relaxed, no-fuss way.

With a Blazer

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If your office allows you to wear denim but you’re still worried that a jean skirt is too casual, slip on a blazer. The sleek, structured piece will help to pull your look together, even if the rest of the outfit is somewhat dressed-down.

We Still Have No Clue What to Wear to the Office, So We Asked Stylists for Outfit IdeasWith Sneakers

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We’ve stressed over what shoes to wear with flared jeans, and finding the appropriate footwear for a denim skirt outfit often feels just as tricky. The good news is that when it comes to fashion, anything goes. So slip on your favorite sporty sneaker (or Converse or Vans) to give this piece an athleisure spin.

With Other Denim Pieces

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When all else fails, denim-on-denim is an easy outfit idea that still packs a punch. Then, once you have this base, add a fun pair of shoes or a sweater you love, giving this classic pairing a personalized touch.

With a Crop Top

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Play around with proportion by styling your jean skirt with a crop top. You’ll create interest pairing a maxi or midi-length jean skirt with a stomach-baring sweater or tee, turning this simple denim design into something 𝑠e𝑥y.

With Lots of Layers

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In many ways, maxi and midiskirts are wearable blankets, so if you’re pulling together a jean skirt outfit during the winter months, you won’t have to worry about warmth. Simply layer your long denim skirt over knee-high boots and tights, then pile on the sweaters, button-downs, and jackets to complete this seasonal ensemble.

With a Cardigan

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While many may associate long jean skirts with the ’90s, a mid-length option can help you channel 1950s and 1960s fashion, too. Style the piece with a cardigan, a thick headband, and T-strap heels to create a playful retro outfit.

With Statement Heels

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Even if you’re wearing your long denim skirt with a bulky sweater, you can still make your outfit feel fancy with pointed-toe heels. Bonus points if your pick is a bright, bold color, which will pop against your neutral bottoms and give your outfit some flair.

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