Looking for outfits with plaid skirts that work for each season? We’ve compiled our favorite plaid skirt outfits in every style!
If there’s a timeless fall piece that never leaves the spotlight, it’s a plaid skirt. Despite having a print, plaid is astonishingly versatile and can be worn in various styles and on different occasions. A plaid skirt can be worn with a day outfit just as much as it can be flaunted on a night out.
Derived from the original Scottish Tartan, plaid skirts are usually made with wool, tweed, and other thermal fabric, which is why their use of them during the cold season was popularized. As time progressed, plaid started to appear even in formal wear, like blazer suits and long pencil skirts.
To learn how to style this incredible piece, stick with us until the end of the article. We’ll share tons of outfits with plaid skirts that will work for any style!
What To Wear With A Plaid Skirt
Here are our favorite pieces to pair if you’re wondering what to wear with a plaid skirt.
Since plaid skirts are made for the cold season, it is just fitting to wear them with a chic turtleneck top! To complete the fit, find a nice pair of knee-high boots and translucent tights. If the weather is not quite cold just yet, a sleeveless turtleneck top, stockings, and close-toed mary jane shoes will do.
The good thing about plaid skirts is that you can pair them with basics and still look polished. Plaid is already a statement piece itself, so you don’t have to worry about finding bold accessories to buff your look.
On the other hand, a good quality white shirt with a good stretch and a nice fit is a wardrobe must-have. If you still don’t have a go-to white tee that goes with almost every bottom in your wardrobe, this is your sign to invest in one now.
Vintage Rockband Shirt
As ironic as it may be, plaid also found a path to rock ‘n roll and grunge fashion. References date as early as the 1970s, when unconventional music and art culture were introduced to the youth.
To style a plaid skirt with a rock band tee, add fishnet stockings, and a pair of ankle boots.
There is an unsaid struggle of keeping tucked blouses in place. Tucking shirts & blouses may also cause an awkward bulge on the upper part of the skirt unless you do it just right. A fitting solution to that would be a cropped top or a box-type blouse, shirt, or sweater.
For A-line skirts, a fitted cropped top would be the best option. For fitted pencil skirts, a loose-cropped blouse or sweater would be great. In most cases, the size and shape of the ideal cropped top still depend on your body shape.
We especially like incorporating crop tops in our plaid skirt outfits for a night out.
Top & Blazer
Another favorite piece that I enjoy styling with plaid skirts is a blazer. Blazers easily make any outfit look sophisticated, smart, and well-thought. To achieve this high-fashion look, put on a belted blazer over a discreet top for securing optimum coverage. You can choose between a mini plaid skirt or a flowy A-line plaid skirt.
Matching Plaid Blazer
If the blazer matches your skirt, so much the better! This look gives chic ‘80s, “Clueless”, Alicia Silverstone energy.
This ensemble would be great with a decent white sleeveless silk undershirt, white knee-high socks, and white penny loafers. If you’re looking for a more subtle, modern look, you can switch up the white socks and shoes with all black. For a sophisticated, high-fashion look, you can scrap the pleated mini skirt and wear a belted blazer, a matching mini skirt, and knee-high boots.
Nothing else defines “Academia” with plaid skirts better than a dark knitted vest. Knitted vests can be worn with a button-down shirt or an oversized t-shirt. I prefer to wear a pleated plaid skirt for this ensemble to achieve the “Academia” look. To finish off, put on high-knee socks and chunky loafers.
If it’s still too warm to put on more than one layer, you can always stick with a button-down. Button-downs give plaid skirts a polished and smart look, which makes them a great candidate for special occasions, work, or dates.
The type of footwear you would want to wear also depends on the type of plaid skirt you’re wearing (pleated, mini skirt, pencil skirt). For minis, knee-high boots can strike the perfect visual balance. For longer skirts like A-lines, ankle boots and loafers are your best bets.
Another hipster style to style plaid skirts is by putting on a Canadian Tuxedo or a denim jacket. Underneath it, you can wear a white or black tee. This ensemble is particularly great for seasons with fluctuating weather because you can easily tie the jacket around your waist and put it on when the temperature starts to drop.
Denim jackets also have optimum thermal support because of the thick fabric, which makes them a handy and practical fashion piece to wear or carry around.
Polo & Sweater
If you’re still not over preppy academia, this one’s for you! To give your button-down and plaid skirt outfit a little oomph, just put on a sweater and pop the collars out. If you’re after the Alicia Silverstone “Clueless” vibe, you can put on a chunky headband for a clique girl look. You can finish off with white sneakers or chunky penny loafers.
Adding a trench coat over any ensemble can easily turn your look into a sophisticated look. Some of my favorite trench coats to pair with plaid are leather and khaki coats. During winter, a furry, off-white trench coat looks great too!
Black Sheer Top
Plaid skirts don’t have to be limited to fall ensembles. If you want to wear your favorite plaid skirt to a night out, you can wear them with a dressy black sheer top with open-toed stiletto heels. If you simply want to achieve a polished look for a special occasion, embellished loafers would be perfect.
Sheer can be used as a cover-up over a showy top or the main top. Make sure you wear a presentable and lacey brasserie if you’re planning to use sheer as the main top.
There’s nothing cozier than a chunky sweater with a thermal plaid skirt on a fall afternoon. A chunky sweater is great for romanticizing your life in a local café. Personally, it’s something I would wear during me-time sessions or on cute dates. It easily makes you look so huggable! Plus, the plaid skirt keeps the theme with the season.
We all have those days when we need a little more thermal support! Tights are stylish, practical, and useful, especially when the temperatures are low.
Apparently, the only way to wear a skirt during winter is to wear tights underneath, at least in some circles. Tights can be worn with an A-line plaid skirt or a mini skirt.
Shoes To Wear With Plaid Skirts
Typically, shoes with your plaid skirt outfits will make or break the look. Here are some of our favorite shoes if you’re wondering what to wear with plaid skirts!
If you love fall fashion, then you can’t let the season go by without wearing knee-high boots! Knee-high boots are versatile, sophisticated, and stylish, and they are considered to be a part of the outfit as a statement piece rather than a subtle accessory. When you wear knee-high boots with a plaid skirt, wear them with subtle and simple basics so as not to overdress.
Plaid skirts are part of oxford, literary, and academia fashion. So if you’re leaning into this type of style, I suggest wearing your plaid skirt with classic penny loafers, slip-on, or clogs.
For a relaxed fit, slip-on loafers are the most ideal. Loafers are versatile and can be worn all year round, which makes them a great fashion investment.
Mary Janes or doll shoes are cute, adorable, and feminine. They are also considered as literary as penny loafers because of their classic and modest look.
When wearing a mini plaid skirt, you would want to wear knee-high socks for a bit of creative layering. When wearing a longer skirt, you can wear them with invisible/foot socks for a dainty and balanced look. For alternative footwear, you can wear ballet flats with long plaid skirts as well.
Chunky Combat Boots
A plaid skirt also works well with chunky combat boots to get a grungy feel. Combat boots give an edgy and streetwear twist to plaid skirts’ association with conservative and literary styles.
When wearing combat boots with plaid skirts, adding in other biker elements like leather and studs can boost your whole look. If you want to keep it simple, a white shirt, a green plaid skirt, and combat boots can work as perfectly.
A travel-friendly pair to wear with your plaid skirt is white sneakers. White sneakers are great because you can wear them with just about anything in your wardrobe.
Ideally, if you plan to wear bulky “dad” sneakers with a plaid skirt, you would want to choose a mini or short one to pair it with. On the other hand, if you’re wearing canvas sneakers with a lighter and dainty silhouette, you can pair that with a longer skirt. This ideology balances the visuals of an outfit which is important in styling ironic pieces together.
Outfits With Plaid Skirts To Wear Right Now
A street-style take on the classic school girl silhouette is brought by this black statement hoodie, 2000s-inspired sunglasses, and chunky military boots. The Burberry purse with a yellow chain makes this outfit pop as well!
If you’re still not over that modern clueless aesthetic, then this outfit is for you! To achieve this look, you only need a button-down with soft, chiffon fabric, a fitted sleeveless top or a corset, a mini skirt, and high-cut stockings. Knee-high socks work too! To complete the look, add some dainty pearl jewelry.
For a modest and smart look, you can opt for a longer plaid skirt paired with a black knitted sweater and close-toed heels. This is one of the best outfits with plaid skirts for meeting clients and attending special occasions during the fall.
Looking for outfits with plaid skirts that feel a bit more casual? Here’s another take on the previous ensemble in a street-style version! To turn this modest look around, you can switch the knit sweater for something more flashy, like this Fendi x Fila logo sweater and oversized belted skirt.
Bomber jacket, white tee, pleated plaid skirt, high-cut socks, and hiking shoes. This outfit can’t get any more comfortable! This one’s perfect for uni or for travel, or wherever (and whenever) you need the style and comfort to boost your mood.
A blouse too dressy to pair with a long plaid skirt? Just wear a white t-shirt! To make your outfit pop, you can add bold-colored shoes or a statement bag. If you’re aiming for a slimmer silhouette, you can switch up the shirt in the picture for a more fitted shirt.
Still trying to look like a ’90s it-girl? Here’s a chic outfit for you: a knit sweater, a plaid mini skirt, high-cut white socks, and close-toed block heels. For a youthful look, you can add a matching chunky headband.
If you’re leaning into a more classic style, then this is one of the perfect outfits with plaid skirts! Flaunt this elegant look by wearing a corduroy blazer, an oversized scarf, a classic knee-high plaid skirt, and statement heels. Add a bejeweled purse for a stylish plus!
Want to achieve a chic argyle/literary look with your outfits with plaid skirts? Here’s a fall fit for you: a green knitted sweater, pleated mini skirt, tights, embellished penny loafers, and a beret. Don’t forget the baguette bag to complete the look!
Punk hipster vibe? This outfit got you! Pair your mini plaid skirt with a black graphic shirt, cropped denim jacket, and a pair of lace-up combat boots. For a stylish plus, you can carry a canvas tote bag with you for a whole hipster look.
Going on a date? Here’s a cute, feminine outfit for you. Find a dressy top and a pair of dainty shoes to pair with your plaid slit skirt. Now all that’s missing is a bouquet of flowers!
This outfit is also perfect for roaming the streets of Paris or Europe. So chic!
Run the show with an oversized pleated skirt! Love the luscious, well-thought layers on this one. Something you would be confident to wear on the streets of New York. Bold, edgy, and stylish – are the three main things that New York street style love.
There’s something familiar and elegant about this classic fit. Its elements are derived from different points in history which makes this interesting and thought-provoking. If you want to achieve this fit, look for these: a turtle neck undershirt, linen vest, wool blazer, below-the-knee plaid skirt, and penny loafers.
Plaid on plaid? Why not! I love how experimental this outfit is. From the printed scarf, the plaid shirt, and the plaid A-line skirt. The mismatched size of her plaid pieces also creates character, depth, and individuality in this outfit.
If you’re aiming for a clean and smart fit, then matching your plaid skirt with your blazer is the answer! Add a pressed button-down and stiletto heels to finish off this ‘expensive look.” This is one of our favorite plaid skirt outfit ideas for an ultra-chic, high-powered look.
There’s something about this ‘Christmas Tree’ silhouette that speaks its own charm! The oversized wool blazer and the A-line skirt just look absolutely perfect with those knee-high boots.
Anything with fur on it can turn any ensemble into a sophisticated and ‘expensive’ fit. The length of this coat also matches the mini skirt – giving minimal exposure to the legs. I like how this rose-colored coat looks with her burgundy top and muted plaid skirt!
Incorporating color into an outfit with a classic plaid skirt can be intimidating, but possible! I love how memorable, vibrant, and glowing this collection of colors looks when put together. It matches her skin undertone too!
Holidays are just around the corner! Even with only colors in this outfit, you can see how vibrant and nostalgic red can look with plaid. Overall, I love how clean, smart, and chic everything in this outfit is put together. This is one of our favorite plaid skirt outfit ideas for the holiday season!
This plaid skirt reminds me of the Scottish Tartan. The way it is worn with the knitted sweater and the boots look so stylish. I think the historical reference in this fit is pretty evident, which makes it an iconic look. This look can be androgynous as well!
Street style is about combining ironic pieces, like this football sweater, this plaid pencil skirt, and high heels. This is one of our favorite plaid skirt outfit ideas for a super colorful look!
Want to keep that petite, clique girl silhouette? The best way to achieve this style is by pairing your plaid mini skirt with a baby tee like this. Put on white sneakers with high-cut socks for a sporty, preppy look!
Gothic school girl? Achieve this look by incorporating lace and sheer elements as above.
Keep it “in-theme” by pairing your plaid mini skirt with an argyle cardigan. You can switch that up to a vest if the temperature rises.
Not a fan of color blocking? No problem – look at how this vibrant-colored plaid skirt works well with this beige knitted sweater and white sneakers. This is one of our favorite plaid skirt outfit ideas for the fall season!
Nail this classic ’50s Parisian silhouette with a flowy, A-line plaid skirt! Add a beret for a nice accent. This is one of my favorite outfits with plaid skirts for the holiday season.
Too warm out but still want to wear your cardigan? A great way to keep it on is by reducing your layers. Skip the undershirt and wear the cardigan as a top, and you’re good to go!
If you love playing with layers, then this fit is for you. Practice your fashionable free will with a black graphic top, a classic blazer, a maxi plaid skirt, and matching boots.
A mini plaid skirt can look to bare – especially if your main silhouette is fitted. You can add dimension by putting on an oversized blazer on your shoulders, like a cape. This is one of our favorite plaid skirt outfit ideas for city living!
Looking for plaid skirt outfits with that grunge vibe? Show your hipster-rock personality by pairing your plaid skirt with a vintage rock band shirt and arm sleeves for a bit of dimension in your plaid skirts outfits.
Here’s an outfit to bring out the ‘university girl’ in you – one of my personal favorite dark academia outfits with plaid skirts. A button-down, a pleated mini skirt, and a complimenting blazer.
Or, you can just wear it casually by wearing your shirt out and adding fishnet leggings for fresh, unique, and laid-back plaid skirt outfits.
You can also style this schoolgirl pleated skirt with witchy complimenting pieces, like this witchy sheer top and starry leggings, for more mystical plaid skirt outfits.
Can’t choose between four colors of plaid when picking your plaid skirt outfits? Then wear them together! I’m not sure if you’ll find something like this in a local shop, but reworking your own plaid skirt would be awesome!
This is one of my favorite outfits with plaid skirts in a monochrome look. Break the ice by wearing your straight-cut midi plaid skirt with a popping oversized sweater. Finish off with dainty heels to highlight the upper part of your body.
Look like a model-off-duty by wearing all-black with a Burberry plaid skirt. Add some chains for a bit of an accent and you’re ready to go! This is one of my favorite outfits with plaid skirts for the winter, especially if you’re looking for a city vibe.
Hopefully, this post gave you lots of ideas for how to style plaid skirts! Enjoy!