10 Classy Plaid Shirt Outfits to Wear Now

How to Style a Trendy Plaid Shirt

Street style woman in plaid shirt and leather skirt

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The plaid shirt is a must-wear dressing piece for fall fashion this year. The classic flannel has been everything from a preppy essential to a grunge uniform, but these days, it is more of a wardrobe staple for women. You may be surprised at how versatile one can be in your wardrobe, pairing well with everything from the expected jeans, to track pants, pantsuits, and even fancy gowns (yes, really). Take a look at our favorite plaid shirt outfits right now, with ideas that work for weekends, wearing to the office, and even going out at night.

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With a Leather Mini-Skirt

Street style woman in plaid shirt and leather mini skirt and trench coat and loafers
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Just like adding a denim jacket to dressy outfits, wearing a plaid top with fussier wardrobe pieces is a great way to bring them down to earth, and extend their wearability. Here, an expensive leather skirt looks cool for the weekend, worn with a blue checkered shirt, a navy trench coat, and easy slip-on sneakers.

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Get Into Layering

Woman wearing white trousers and plaid shirt and black coat for fall fashion
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An unbuttoned flannel can be a handy layering piece for fall. Here, it's worn open, under a lightweight fall coat, to add cozy warmth — and a welcome touch of pattern — to a simple outfit of a white t-shirt and jeans. You could also layer this shirt underneath a jean jacket, for a casual layered look that works well for weekends, whether you're walking in the woods, or just chilling at home with friends.

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Wear It With a Maxi Skirt

Street style woman wearing a Burberry plaid shirt and black maxi skirt
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Want an easy way to keep wearing your go-to maxi skirts through the fall months? A cozy flannel shirt instantly makes a long, solid-colored maxi skirt feel more cozy. This fashion influencer is wearing sandals, but if you live in a colder climate, choose easy flat loafers or ankle boots to wear with this outfit.

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Wear It to Work With Trousers

Woman wearing ruffled plaid blouse and black trousers and orange purse
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A plaid shirt in a classic beige, red, and black pattern matches perfectly with black trousers. Update this chic office outfit by adding bright, autumnal accessories, such as the beautiful pumpkin-hued purse pictured here.

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Wear It Over Track Pants

Street style woman wearing a plaid shirt and track pants and loafers
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We love the current athleisure trend of wearing gym essentials as fashion separates, and here's a great way to participate this fall. As seen here, your essential flannel looks fashion forward when worn loosely over cuffed track pants. Leather loafers and a high quality purse help to pull together this surprisingly stylish weekend outfit.

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With a Pantsuit

Woman wearing a pink pantsuit and plaid blouse
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The colorful pantsuit for women is a major fashion trend that we're loving this year. Here, a checkered shirt adds a touch of whimsy to a stylish, feminine pantsuit in candy pink. You could choose a shirt color that contrasts with your suit's shade for major impact, as pictured, or play it safer with a black and white shirt, which acts as a neutral, pairing well with any color. We're loving this fashion influencer's matching shoes, too!

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Wear It As a Jacket

Woman in black dress and plaid shirt
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Worn unbuttoned, a flannel shirt can be worn as an easy top layer. Think of layering it over anything you would normally wear a jean jacket with, to dress down fancier outfits and make them wearable for more occasions. As pictured here, it makes an unexpected jacket for layering over a fancy black dress for evening.

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Collar and Cuffs

Woman wearing a long sleeveless camel coat and plaid shirt and shiny pants
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Now that plaid shirts have become so popular, you'll find plenty of variations on this trend in stores. We like how the French cuffs and collar on this button-down plaid shirt give it a more sophisticated look, that matches well with fancy trousers, as pictured on this fashion show attendee. You could also wear this shirt easily to the office, or for interviews this fall and winter, with a black pencil skirt, black pumps, and a black leather satchel.

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With Leggings

Woman wearing a plaid shirt and black leggings and pink jacket for fall fashion
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What could be easier for casual weekend days than a boyfriend-style flannel pulled on over comfy leggings? You could wear this easy, day-off outfit with sneakers or flat ankle boots, for a laid back look.

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Plaid Shirt and Jeans

Street style woman in plaid shirt and jeans
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People have been wearing a flannel shirt and jeans for fall fashion every year for what seems like forever. Tuck your shirt into high waisted skinny jeans to show off your shape, or let it fall free. Either way, this look is a classic!