22 Best Pick Plaid Skirt Outfit Styles for Any Season

The ’90s were an exciting decade filled with blockbuster films, new music, and technology. It’s no surprise that these cultural landmarks found their way into 90s inspired outfits, which are becoming trendy again!

Taking cues from Cher Horowitz’s iconic style from the movie Clueless, one nostalgic piece that stands out from the latter is the 90’s plaid skirt outfit

Plaid is one of those prints that never go out of style. It’s timeless, classic, and can be paired with pretty much any outfit.

In recent years, fashion designers from all over the world have created their own versions of the plaid skirt, a staple item for your wardrobe. Warm, cozy, and memorable, the tartan plaid skirt has been rotating in and out of style since the ’60s. 

While the first image that comes to mind is a red plaid skirt outfit, the print is available in various colors and styles, from pastels to brighter hues. You can choose from a variety of mini, long, midi, flowy, or pleated skirt designs that are sure to compel you to dress up.

So, if you’re looking to create cute 90s outfits that nail school core and light academia, look no further. Keep scrolling for our top picks.

High-End 90s Plaid Skirt Outfit Ideas

Plaid skirts are incredibly versatile; thus, unsurprisingly, there are a lot of iconic 90s outfits to help inspire you.

Whether you prefer classic cuts, experimenting with vintage, or something more modern, these top designerwear looks are worth trying out.

Victoria Beckham Pre-Fall Plaid Chiffon Skirt

Victoria Beckham is renowned for her unusual approach to fashion design. This classic 90’s plaid skirt outfit adds contemporary flair with its refreshing and unconventional lilac color palette.

If you’re unsure about what to wear with a plaid skirt, the chiffon skirt comes with a tailored top for that effortless pajama-like aesthetic.

The matching separates also feature grain-cut panels to create fluid drapes or curves when worn.

Additionally, this 90s look draws on inspiration from monk garments. Therefore it features a comfortable, baggier fit with more focus on the direction of the plaid pattern itself. 

Nº21 Midi Pencil Skirt

woman posing with bag

Thanks to its flattering cinched waist and subtle pleating detail, the Nº21 midi-skirt is sure to become a wardrobe staple.

With its multicolored plaid patterns and subtle back slit, the plaid skirt outfit strikes a balance between feminine and bold.

Create a more sophisticated 90’s plaid skirt outfit by incorporating the midi skirt into your daily office wear. Or, for a striking contrast in your streetwear style, pair the refined skirt with an oversized sweater or jacket. 

70’s Inspired Zara Pleated Plaid Skirt

woman posing with bag

A pleated skirt adds volume and balance, looking great on any body type. This is why this Zara pleated piece is highly versatile and can be worn for any occasion, both formal and informal.

Furthermore, the minimal plaid pattern is easy to match with other garments and never goes out of style.

The accordion folds give you breezy, elegant styles that are fashionably fluid. For the ultimate 90’s plaid skirt outfit, pair the Zara pleated skirt with a simple tee and sneakers.

Alternatively, you can layer the skirt with a blazer and a pair of boots for a creative twist on corporate style. 

Halogen Plaid Pencil Skirt

woman posing

Swap your trousers and pants for this chic 90s look appropriate for workwear! This figure-skimming pencil skirt will become a wardrobe staple with its multifunctional mix of classic plaid and subtle details.

However, pencil skirts aren’t just for the office. The side zipper modernizes this 90s dress style.

To bridge the gap between conservative and cool, revamp the classic skirt with an oversized tee or crop top and playful accessories. 

MONSE Paneled Wool-Blend Asymmetrical Skirt

woman posing

One print is never enough. MONSE’s Asymmetrical skirt features a blend of alternating prints and unique patchwork to make you think outside the box.

Designed in Italy, the 90’s plaid skirt outfit reimagines the wrap skirt, adding a quirky finish with its asymmetric silhouette that shows off your curves.

Combine it with a cardigan, minimal accessories, and simple shoes such as flats or low block heels. You can also layer the 90s skirt with monochrome or denim to allow the plaid pattern to shine bright. 

Le Kilt Blackwatch Plaid Skirt

woman posing

Le Kilt’s Blackwatch plaid skirt draws on tartan kilts for inspiration in a nod to Scottish heritage.

Although this A-line plaid mini skirt outfit may feel rather traditional, the leather side belts and hand-fringed edges add some grunge.

Finished with a kilt pin, the pleated skirt is available in different colors.

You can nail the preppy look with a pair of chunky loafers and tucked socks. For a more playful 90’s retro outfit, throw on a graphic tee and combat boots. 

Tomas Maier Chequer Plaid Skirt

woman posing

You can never go wrong with a red plaid skirt outfit. The Tomas Maier Chequer Plaid skirt can spice things up if you are bored with neutral or solid-colored skirts.

Wear it with a black turtle neck and Chelsea boots for an adorable, feminine look. Another option for a more sleek 90s dress style is to finish off your look with an oversized single-color or matching plaid blazer. 

Robert Rodriguez Lace Wrap Skirt

woman posing

Once reserved for princess dresses and doilies, lace has recently made a high-fashion comeback. To make a lacy statement, the key is going for the unexpected such as this Robert Rodriguez plaid wrap skirt.

Finished with a unique, asymmetric hem and delicate lace trim, this feminine skirt can be dressed up or down to recreate the 90s looks for ladies.

Are you heading to a special event? Pair a satin blouse and strappy heels with the wrap skirt to look polished. Or, for a more casual 90’s plaid skirt outfit, combine it with a pair of pumps and a cropped t-shirt or sweater. 

Trendy Plaid Skirts That Won’t Break the Bank

Instead of overspending, you can still dress your best while on a budget. The following plaid skirts will make your 90s attire goals a reality and ensure your outfits are on-trend. 

Lulus Spence Navy Blue Plaid Skirt 

woman posing

Make a statement in this soft, felted wool-blend flannel skirt that features a classic A-line silhouette. With a high, darted waist and mini hem slit, the navy blue and white patter transcends into a trendy 90’s plaid skirt outfit

Balance the preppy vibes of the skirt with an asymmetric or crew neck top. However, for the perfect fall fit, pair with knee-high boots. 

Lulus Mad for Plaid Taupe Miniskirt

girl posing

If you enjoy prints, the Mad for Plaid miniskirt is a perfect choice for you. With specks of rust orange, beige and blue, the soft woven flannel gives way for comfort and warmth.

To refresh your 90’s plaid skirt outfit with this statement piece, experiment with color blocking other elements of your look. You can also throw on a chunky sweater, turtle neck, or hoodie to elevate your winter wardrobe. 

VERO MODA Kenso Plaid Miniskirt 

girl posing

Inspired by a 90’s retro outfit, this classic checked pattern is timeless. The Kenso high-waisted miniskirt will look fantastic with a classic white sweater or long sleeve top.

Additionally, you can add a long overcoat for extra coverage.

Or, if you want to transform your outfit into something more playful, throw on an extra print. Finally, finish your outfit with your favorite knee-high or ankle boots, and you’re good to go. 

ASTR the Label Christa Plaid Mini Skirt 

girl posing

The Christa high-waisted mini skirt has a vented front featuring two subtle slits and an abbreviated hem. However, what sets this plaid mini skirt outfit apart is its use of houndstooth. A variation of traditional checkers, the houndstooth print features notched corners. 

To style an easy 90s outfit, pair the Christa mini skirt with a brown or black shirt. Dress down and let the skirt speak for itself.

Sage the Label French Duo Multi Plaid Mini Skirt 

woman standing

This must-have mini skirt is the perfect statement for your next 90’s plaid skirt outfit. Shaped with a flattering high-waist and A-line shape, the soft woven fabric will give your sweaters some competition. The skirt is finished with a fringed, mini hem for a touch of edginess.

Pair your skirt with a long-sleeved bodysuit or shirt for a chic black plaid skirt outfit. You can also opt for minimal accessories for major clueless vibes.  

Top 4 Plaid Tennis Skirts

If you prefer wearing skirts over jeans, you’ve probably noticed that tennis skirts have made a comeback in recent years. For a sporty and stylish look, these plaid tennis skirts will help you catch up to the 90 clothes trend. 

BB Dakota x Steve Madden Check the Time Skirt

girl posing with a bag

The timeless plaid pattern paired with a crisp, pleated skirt makes this piece of apparel a statement. So whether you’re looking for something sporty or elegant, the Check the Time Skirt will give you your fill of preppy fashion. 

To create bold, statement accessories, try matching the print from head to toe. Whatever you have will work to make this look effortless.

For balance, add monochromatic accessories such as white booties or jewelry. If you’re feeling daring enough, create some dimension using socks. 

BP. Amanda Tennis Miniskirt

cute girl posing

Functional and transitional, the BP tennis skirt features a fitted waist and flared, tuck-pleated hem. A very fashion-forward yet sporty piece, the miniskirt is completely fall-appropriate, so you don’t have to worry about feeling cold.

You can create a nostalgic 90’s plaid skirt outfit with the miniskirt and a varsity jacket. Or, pair it with tights and a sweater for a more fashion-conscious look. 

Alice + Olivia Emilie Box-Pleat Mini Skirt

woman standing with a bag

The Alive + Olive Emilie Box-Please mini skirt is crafted in eclectic, two-tone tweed fabric for extra dimension.  This playful and feminine skirt comes with a matching blazer for a party-ready 90’s plaid skirt outfit

Wear the Emilie Mini Skirt with a white button-down. Or go bold and don’t be afraid to wear the bright pink on top and bottom. You can also wear mary jones or classic flats with sheer socks for a more sprint-like look. 

Free People Honey Pleated Retro Skirt 

girl posing

This skirt features a high-banded waist and flattering skater silhouette for the best of athletic and avant-garde.

With the Free People honey skater skirt, you’ll never be out of style. Made of stretch fabric, the skirt features pleating for a flattering silhouette.

Furthermore, the retro-inspired pink and yellow plaid makes it more striking. To complete your 90’s plaid skirt outfit, pair the skirt with all-white accessories and boots.

Timeless Plaid Mini Skirts

As with most iconic fashion trends, plaid never goes out of style. But thanks to a love for 90’s prints and styles, plaid has made a resurgence, slowly becoming one of the most effortless and trendy styles. The following plaid skirts will finish off any 90s inspired outfits

Alice + Olivie Renna Button Wrap 

woman standing

Screened with houndstooth motifs, the Renna button wrap makes an elegant addition to your collection. The skirt is structured in a wrap style with exposed button detailing for that extra school girl charm. 

To keep your 90’s plaid skirt outfit elegant and sleek, pair it with a button-down shirt. Then, for extra polish, add a belt and slip-on. 

Self-Portrait Buffalo Plaid Cotton & Wool Blend Skirt

woman happily walking

This schoolgirl-inspired skirt is made of classic black and white checks with bejeweled button detail on the pocket flaps. This practical skirt can be worn year after year without running out of plaid skirt outfit ideas.

Additionally, the warm wool used for such blanket-style skirts keeps you warm through the winter. 

While plaid is an interesting pattern, it pops even more when paired with a contrasting print. For example, try layering polka dot or geometric print tops with the Buffalo Plaid Skirt for an artistic 90’s plaid skirt outfit

Toccin Flap Patch Pocket Mini Skirt 

woman posing

This contemporary flap pocket mini skirt from Toccin features an A-line silhouette and a button-down front. The hem falls just above the knee, so you can skip leggings or tights if you’d like.

Since the skirt already features a lot of detail, you can wear it as part of a simple 90’s plaid skirt outfit and still look great! 

For a more sophisticated outfit, you can wear the Toccin flap patch mini skirt with a white button-down or layer with an overcoat. 

Alice + Olivia Semira Pleated Mini Skirt

woman standing

An important element of your all-year-round wardrobe, this Alice + Olivia pleated 90s skirt demonstrates flexibility. It’s just as easy to wear and style as your favorite pair of jeans or trousers.

The skirt features a back zip, pleated detailing, and specks of orange pattern for a little extra something to the classic plaid print. 

We recommend color blocking this 90’s plaid skirt outfit with a bright color such as orange. This will create a statement look with a plaid twist. 

Maje Jelingan Navy Blue Plaid Mini Skirt 

girl posing backwards

A timeless plaid print miniskirt, this Maje Jelingan piece features a belted twist for major ‘90’s appeal. You can style the timeless plaid print with any ensemble for a seamless 90’s plaid skirt outfit.

The skirt has a cinched turned-over waist and A-line silhouette complete with pockets. To go the extra vintage mile, tuck in a white flowy shirt and pair the skirt with a statement choker. 

Alternatively, you can try to add some complexity through additional layers. For example, throw on a contrasting burgundy trench coat for added finesse. Or, you can wear a printed t-shirt to add some dimension to your look.

Since the skirt already has a uniform-like style, a button-down shirt would also be a great addition to your outfit. 

Are you Ready to Head Back to the ’90s? 

Plaid, like other iconic fashion trends, has been reworked several times during its time on the runway. Casual plaid skirts retain a certain schoolish charm when styled as a statement look. 

Instead of reproducing your favorite celebrity looks, add your own individual charm to update and modernize the plaid skirt.

The goal is to appear to be on-trend while appearing effortless and laid back, like the ’90s. Don’t forget to have fun with your style adventures and embrace the carefree, youthful vibe set out during the era. 

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