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The symbol of preppy style – the plaid dress. A plaid print brings a vintage yet feminine touch to your outfits and can be styled up in various ways. It’s a timeless print that will refresh your wardrobe in a flash. It’s not one of those cases where you’ve seen one plaid dress, you’ve seen them all. You can rock a plaid dress in innovative ways and show off your fashionista side.

Whether you dress it up or dress it down, you won’t get enough of this iconic wardrobe staple. Though it can be worn all year round, it’s a particular fall/winter favorite – especially in darker shades such as burgundy, grey and forest green. In the warmer seasons, it can be styled in pastel and neutral tones. No fashion faux pas here!

From street style inspiration to blasts from the past, we are inspired by so many different ways of styling. Innovative ways that we may not have even thought of! Plaid dresses don’t have to be worn alone, but can be part of some playful layering or a touch of customization. You can really create your own take on the classic plaid dress, inject a bit of authenticity!

Here are some of our favorite outfits to help you get your creative juices flowing!


90s’ Style

A plaid cami dress screams 90s’ styling and we are here for it! Layering it over a cap sleeved tee will make it the perfect transitioning outfit between fall and winter.

Swap the t-shirt for a slim fit roll neck to bring it into winter. A belt will make the outfit less grunge and more feminine, and will show off your figure. The vinyl ankle boots add an edgy touch. 

Street Style Heaven

Women wearing a long plaid dress with slit at the back and retro sunglasses

Via Man Repeller

When we think of Fashion Weeks past and present, we think of badass street style outfits such as this one. It’s so easy to replicate – it is effortless and elegant.

We love the idea of layering a bandeau plaid dress with a sexy slit over a high neck knit, turning your summer occasion dresses into something sassier for fall/winter.

A low bun adds a touch of sophistication along with pearl earrings, a timeless classic! To battle the winter chill, finish the look off with a longline puffer coat in navy for a really dramatic look worthy of any Fashion Week.

This outfit is perfect for taking you from desk to dinner – ultimate girlboss in the boardroom and turning heads at the bar.

Preppy Perfection

We mentioned that plaid dresses were the symbol of the preppy look – this outfit is the perfect example. Layering a school girl-inspired plaid dress over a frilled blouse is something reminiscent of Blair Waldorf in Gossip Girl.

Pinafore dresses are ideal for layering – lightweight blouses in the warmer months, and just swap for some cute knitwear when it gets chilly. It’s that simple!

A slither of red lippy to match your shoes is the level of detail we love! For the colder months, team the look with a navy peat coat to match the forest green and navy print dress.

Babydoll Beauty

Babydoll dresses are ultra-flattering on all figures, their drop style is perfect for hiding sins and highlighting your best features. This plaid mini dress is in an effortless loose fit and paired with over-the-knee boots, combines naughty and nice.

Finish the look with a navy perfecto leather jacket to show off the high babydoll waist. If you want to show off your figure, place a black leather belt with a masculine western-style buckle to cinch you in at the waist. And voilà!

Oh So Retro

If you love retro styling, then a flared plaid dress layered over a black high neck knit will remind you of something you have seen in a film. The fitted waist cinches you in at the waist and creates the perfect hourglass silhouette. The black leather over-the-knee boots modernizes the look and vamps it up – you can never have too much sass!

Sporty Styling

If we told you that even those of you with a sportier style could rock the plaid dress, would you believe us? Well you should! The plaid bandeau mini dress is perfect for layering over a basic tee – it’s stylish, youthful and playful.

The mesh socks add a touch of texture and fun to your outfit. White sneakers and a cross body will be your companions. Want to make it more fall/winter appropriate? Swap the mesh socks for over-the-knee socks to battle the breeze!

Date Night Dress

Women wearing short plaid dress with long sleeves and thigh high boots with black clutch bag

Via Who What Wear

If someone knows how to rock plaid in a chic and timeless manner – it’s Victoria Magrath, aka InTheFrow. This high neck and fitted style make the dress more sophisticated. It’s oversized plaid print makes the dress bolder.

Team it with over-the-knee boots to elongate your frame. We love Victoria’s hair styling here, slicked into a high ponytail so that all eyes are on the dress! We could totally see this for a date night or just for those times you want to dress to impress.

Bohemian Babe

Plaid print can also be worn in a Bohemian style. A midi-length shirt dress in a fit and flare style will hug your figure and move elegantly with every step.

We recommend unbuttoning the last few buttons to show off your fancy footwear – over-the-knee red leather boots to color coordinate with your dress will be the touch of modernity the outfit needs.

Great In Grunge

For a 90s’-inspired grunge look, a maxi plaid dress in a cami style is perfect for layering over your wardrobe basics. From a classic cotton tee to a roll-neck sweater, you can throw this plaid dress over the top and go – talk about effortless!

Creepers are the go-to shoe for a grunge fanatic, and a beret adds a playful touch, especially if you have a bold hair color.

Parisian Preppy

Via Pinterest

Two of our favorite styles – preppy and Parisian, are combined here and make a match made in heaven! Both styles are renowned for oozing sophistication. We can’t get over how dreamy this outfit is!

Layering a plaid dress over a silk shirt with an oversized collar is perfect for getting the best of both worlds. The flared skirt will create movement as you walk and highlight those long legs! Embrace the Parisian style with a bob and bangs, subtle makeup and a statement bag. Elegance at its best!

Casual Chic

Women wearing pinafore plaid dress with red lipstick smiling

Via Pinterest

How can you casually wear a plaid dress? Though it has preppy vibes you can wear it in a more relaxed way. Some of us don’t like being high maintenance!

Layer a pinafore dress over a thin knit! Color coordinate your sweater with a color in your pinafore. This bronze shade makes your skin pop and highlights your on-point makeup. The balloon sleeves add a touch of originality to your look.

For fall/winter, throw your favorite camel coat over the look to keep within the color scheme. A simple color scheme elevates your outfit and makes it look more luxurious!

Also Read:

How to Dress Long Dresses in the Fall – Outfit Ideas & Styling Tips (Women’s Edition)

How to Layer A Dress in Winter (Women’s Edition)

How to Style A Cardigan Over Your Dress – Outfit Ideas & Styling Tips

Girly Gingham

Via Vogue UK

Gingham is a variation of plaid that can help you embrace a retro-inspired look. Vanessa Hudgens rocks this print perfectly with this asymmetric midi dress.

We love the volume it has as you walk, and teaming it with flats takes it from dressy to casual. Add an androgynous vibe with an oversized leather jacket – with those dramatic sunglasses, you will look totally badass!

Acing Asymmetric

Via Who What Wear

If you want a modern take on the plaid dress, then an asymmetric maxi dress will be the one for you! We love Monikh’s outfit – the plaid asymmetric dress in red is a bold fashion statement that compliments most skin tones.

It is edgy and feminine – finish the look off with Buffalo sneakers or creepers for gothic touch. Poker straight glossy hair is the perfect finishing touch.

Office Chic

Via Hello Magazine

Holly Willoughby is a British TV style icon. People study her Instagram feed every day to get inspired by her style. She knows how to rock her figure and embrace her curves.

This pinafore dress is figure-flattering and is in neutral tones, making it easy to team with other pieces in your wardrobe. Layered over a camel knit, you can’t put a foot wrong in this look! Ankle boots will lengthen your frame and will complete your outfit.

Clueless Vibes

Via Storets

We love Cher’s iconic yellow plaid print in Clueless – but how can you modernize it? This fit and flared mini dress with balloon sleeves is the 2020 take on the outfit.

The retro glasses are reminiscent of the 90s and the outfit can be teamed with a black satchel bag for a schoolgirl touch. In the winter, throw an oversized roll neck knit over the dress to wrap up warm.

Also Read:

How to Wear Hats – What Hat to Wear With Your Coat – Women’s Edition

Bohemian Winter Outfits

How To Get The Look: Winter Outfit Ideas

About The Author

May is totally crazy about the 80s and everything the decade inspired! Having grown up in a household that was totally taken over by 80s music and fashion its only natural that May lives and breathes the 80s!

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