15 Nostalgic Denim Maxi Skirts For Transitional Weather

15 Nostalgic Denim Maxi Skirts For Transitional Weather

Skirt enthusiasts rejoice! The denim maxi is back for another season. The versatile and wearable style has returned in full force in fresh cuts, silhouettes, and hues. The trend takes a nostalgic ‘90s and Y2K approach, rethinking iconic looks from stars like Britney Spears and Jennifer Aniston. We’ve also seen the statement-making trend on current streetwear trailblazers like Gigi and Bella Hadid, Julia Fox, and Jennifer Lopez. 

This maxi cut is in line with other retro-inspired denim trends, like the resurgence of baggy jeans along with barrel-legged silhouettes and utilitarian styles. While a floor-grazing denim skirt may seem like a faddish throwaway piece, it has the potential to be the unsung hero of your wardrobe. Why? Because it’s the perfect transitional and multi-season clothing piece. Dress it down with a leather jacket and sneakers, or dress it up with a flowy blouse and kitten heels. (Take it from R29’s fashion director, who styled one denim maxi skirt five ways).

The possibilities are endless, and with so many brands taking on the trend, you’re bound to find an option that speaks to your personal style. Read on to find a mix of denim maxi skirts in both straight and plus sizes with front slits, unique details, and the current obsession: a fishtail shape.

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We The Free Catch The Sun Denim Maxi Skirt

Opt for a flowy floor-skimming denim maxi skirt with seam details lined throughout. The relaxed-fit skirt has that swish effect to it that you’ll adore spinning in.

Shop We The Free At Free People

We The Free Catch The Sun Denim Maxi Skirt, $, available at Free The People

Pilcro The Madi Front-Slit Denim Skirt

The Madi is your new go-to maxi ready to complement all your attire with its soft dark blue hue and lightly frayed hems. Go bold with a semi-sheer top, or don or a button-down for a clean-cut look.

Shop Pilcro At Anthropologie

Pilcro The Madi Front-Slit Denim Skirt, $, available at Anthropologie

Abercrombie & Fitch Two-Tone Denim Maxi Skirt

Looking for a striking statement piece? Abercrombie & Fitch has a two-tone skirt that combines medium and dark washes for a fashion-forward option that is still easy to style.

Shop Abercrombie & Fitch

Abercrombie & Fitch Two-Tone Denim Maxi Skirt, $, available at Abercrombie & Fitch

Good American Denim Maxi Skirt

Good American’s denim maxi skirts are notorious for selling out fast because of their extremely comfortable fit. This style is a prime example: The skirt has more stretch than you’d imagine, resulting in a floor-skimming bottom that you’ll love wearing all day long. And, as a bonus, it’s currently on sale for 25% off.

Shop Good American

Good American Denim Maxi Skirt, $, available at Good American

Madewell Denim Carpenter Maxi Skirt in Handlon Wash

Cargo pants were the rage a few years ago; now the utilitarian trend has influenced jeans and skirts. The oversized pockets and contrast stitching make this a trendy option to wear to the office.

Shop Madewell

Madewell Denim Carpenter Maxi Skirt in Handlon Wash, $, available at Madewell

L’Agence Kailani Denim Skirt

This mermaid-cut denim maxi is a stunning option for work events and night outs. The midnight black skirt hugs the waist and hips for a flattering appearance and drapes into a trendy flared high-low hem.

Shop L’Agence

L’Agence Kailani Denim Skirt, $, available at L’Agence

Driftwood Joanna Maxi Skirt

We’re back with another Free People pick. We couldn’t pass up this Y2K-inspired skirt decorated with floral embroidery throughout. The raw-edge hemline makes it a laid-back maxi that fits the brand’s bohemian theme.

Shop Driftwood At Free People

Driftwood Joanna Maxi Skirt, $, available at Free People

Dynamite Buttoned Denim Maxi Skirt

While this skirt requires some time with buttons, it’s a stylish piece well worth the effort. The fitted piece is a perfect choice to pair with basics, like a chunky sweater or cardigan.

Shop Dynamite

Dynamite Buttoned Denim Maxi Skirt, $, available at Dynamite

ROLLA’s Chicago Skirt

Show off your new pointed-toe boots in a high-rise denim maxi skirt with a front split. The mid-blue wash is reminiscent of your favorite pair of vintage jeans. 

Shop ROLLA’s At Revolve

Rolla’s Chicago Skirt, $, available at Revolve

Venus Denim Button Down Flounce Skirt

Is it Western? Is it cottagecore? Maybe it’s a magical blend of both. The flared and tiered shape brings this skirt to life, while the button front adds dimension. You’d be surprised at the versatility of it, as you can wear it for spring picnics straight into summer festivals.

Shop Venus

Venus Denim Button Down Flounce Skirt, $, available at Venus

COLLUSION Denim Fishtail Maxi Skirt

Distressed is the name of the game. With a high-rise fit, fishtail hem, and kick slit, this maxi skirt has it all. Unlike most denim skirts, it also has a zip closure on the back.


Collusion Denim Fishtail Maxi Skirt, $, available at ASOS

Free People Come As You Are Denim Maxi Skirt

So far, we’ve mostly seen classic blue jean skirts on the runways and from retailers, but there’s always a time and a place for a white denim skirt. This true floor-skimming option can easily be paired with many pieces and styled in loads of ways. It’s the perfect spring staple.

Shop Free People

We The Free | Free People Come As You Are Denim Maxi Skirt, $, available at Free People

Evans Black Denim Midi Skirt

If you’re looking for a true staple piece that you can style any way you want for any type of occasion, this skirt is the one for you. While it has a relaxed fit and elastic waistband that makes it feel comfortable and casual, the dark wash and A-line cut keep it classic and upscale.

Shop City Chic

EVANS Black Denim Midi Skirt, $, available at City Chic

Mango Denim Long Skirt

This slightly elevated maxi skirt has decorative seams around the waist that give it a Western feel. The two-toned, raw-edge hemline also brings another unique element to the garmet. Part of Mango’s Circiular Design Collection, it’s made from recycled cotton-blend fabric.

Shop Mango

Mango Denim long skirt, $, available at Mango

Reformation Nila Long Denim Skirt

Yet another slim-fit skirt with a front slit, this high-waisted style has a unique crossover waistband with a slightly off-kilter button. It’s one that can easily be dressed up with a blouse or dressed down with a baggy T-shirt. 

Shop Reformation

Reformation Nila Long Denim Skirt, $, available at Reformation

Zara Low Rise Long Denim Skirt

We think we found the perfect beach-strolling skirt in this Zara piece. The low-rise waist and ankle-length hem offer an effortless and relaxed feel. Pair it with a crop top for a staple summer outfit. 

Shop Zara

Zara Low Rise Long Denim Skirt, $, available at Zara

Chartou Retro A-Line Maxi Denim Skirt

Channel your inner slam-poetry-in-a-moody-cafe self in this wide A-line denim skirt. This slightly distressed, vintage-inspired style from Amazon comes in a few denim washes and has a multi-button closure for the ultimate flattering and comfortable fit.

Shop Amazon

Chartou Retro A-Line Maxi Denim Skirt, $, available at Amazon

Wash Lab Denim Daily Slit Denim Midi Skirt

And you can’t go wrong with a high-quality, medium-wash denim midi skirt. Add this tried-and true-style to your casual rotation for when you need to put together a quick, no-nonsense look. It’ll be your go-to for running errands and casual outings.

Shop Nordstrom

Wash Lab Denim Daily Slit Denim Midi Skirt in Washed Blue, $, available at Nordstrom

Universal Standard Dakota Denim Skirt

Universal Standard describes this denim midi skirt as “part bohemian, part western, and part fashionably modern,” and we agree. A pencil silhouette with a ram hem makes this style timeless without being boring.

Shop Universal Standard

Universal Standard Dakota Denim Skirt, $, available at Universal Standard

BDG Mandi Denim Maxi Skirt

This style is for anyone looking to channel their teenage angst (or simply peruse a farmer’s market on a lazy Sunday afternoon). The faded wash and pre-frayed hem give this skirt a lived-in, casual feel. But the a-line silhouette and center slit to make it not so basic.

Shop Urban Outfitters

BDG Mandi Denim Maxi Skirt, $, available at Urban Outfitters

GRLFRND Amara Denim Maxi Skirt

This lightly faded denim maxi skirt is non-stretchy yet lightweight. The column silhouette keeps it sleek, but don’t mistake it for boring, especially thanks to its cheeky back slit. 

Shop Net-a-Porter

GRLFRND Amara Denim Maxi Skirt, $, available at Net-A-Porter

Stradivarius STR Denim Midi Skirt with Seam Detail

Made from 100% non-stretch denim, you’re getting a truly structured skirt from Stradivarius. The edgy raw-cut waist, minimal pleating, and light wash are perfect if you’re going for a cool girl vibe. 


Stradivarius STR Denim Midi Skirt with Seam Detail, $, available at ASOS

Pilcro Slit-Front Denim Skirt

For a more dressed-up look, darker denim washes are definitely the way to go. The structure of this straight-cut skirt also makes it slightly more formal and timeless. And again, another slit for the win!

Shop Anthropologie

Pilcro Slit-Front Denim Skirt, $, available at Anthropologie

Urban Renewal Remade Denim Ruffle Maxi Skirt

We love a deconstructed moment, and we especially love a one-of-a-kind piece, and this skirt offers both. Made from global vintage and deadstock fabrics, no two Urban Renewal skirts are exactly alike. This vibrant and slightly flared upcycled piece is truly a denim dream.

Shop Urban Outfitters

Urban Renewal Remade Denim Ruffle Maxi Skirt, $, available at Urban Outfitters

Cider Miss Crafty Patchwork Denim Midi Skirt

Deconstructed denim is another 2023 trend to look out for. Cider’s playful interpretation features patchwork and a slightly bubbled cut. The mix of washes and the midi length also make it a great option for a fun daytime look.

Shop Cider

cider Miss Crafty Patchwork Denim Midi Skirt, $, available at Cider

Sea Flyn Lace-up Denim Maxi Skirt

Not your typical denim skirt, this style has lace-up sides that show off your legs. The skin-bearing details make it perfect for spring and summer. You’ll definitely feel the urge to prance through a field or picnic in this wide, light-wash maxi skirt.

Shop Net-a-Porter

Sea Flyn lace-up denim maxi skirt, $, available at Net-A-Porter

Levi’s Icon Long Belted Light Wash Denim Maxi Skirt

This denim maxi skirt has all of the features of a pair of Levi’s classic jeans. From the five-pocket cut to the classic stitching to the lived-in wash, this skirt is timeless. But the waistband bow tie adds a unique and playful touch to this style.

Shop Lulus

Levi’s Icon Long Belted Light Wash Denim Maxi Skirt, $, available at Lulus

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