Well Plaid: How To Wear A Plaid Shirt

Looking for a few pointers on how to put together a great outfit? Look no further. We made it easy with tons of new, pre-styled, and autumn-approved head-to-toe outfits that will have you dressed and ready for any - and every - occasion. 

THE CLOSET STAPLE: A GO-TO PLAID SHIRT

Nothing says cool and casual quite like a plaid shirt. While it may seem simple, it’s also a closet staple and an effortless go-to that every guy should own a few of. Easy to mix and match and pair with virtually everything, plaid is the pattern that never goes out of style. So many options, so many different looks, somehow each one better than the next, our long sleeve plaid shirts come in a variety of easy-to-wear plaid prints, with the same supreme softness and perfect fit. 

Check out this guide on how to wear a plaid shirt and you’ll be rocking this timeless laidback look in no time. 

BEST IN CLASSIC: BUFFALO PLAID SHIRT WITH JEANS

BUFFALO PLAID SHIRT WITH JEANS

You’ll probably most often wear your favorite plaid shirt in a casual manner, so it’s imperative that you get this look right. Stick to jeans and leather workboots for a simple yet sophisticated, well-put-together outfit.

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When comfort is of top priority and classic style is key, our Belhaven Double Layer Shirt is the one to reach for whether you’re heading outdoors, off to work - or both. With its buffalo check exterior and lightweight, contrasting plaid interior, this long-sleeve button-front shirt is equal parts comfortable, soft, and subtly stylish. Pair it with your favorite pair of tried-and-true denim blues and finish strong with a boot. You can even throw on a hat if the occasion permits. 

LAYER, PLAYER: CHECKERED PLAID LAYERED LOOK

 CHECKERED PLAID LAYERED LOOK

layered spin on a casual plaid look, this outfit works best in transitional weather. A good flannel and a good day go hand in hand, so make your good days great with a super-soft cotton flannel with an incomparably comfortable fit layered over your favorite tee. Pro Tip: Tie your shirt around your waist when the weather gets warm. 

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Our Friona Flannel Shirt is a closet staple for those in-between days. Super-soft and comfortable, lightweight yet warm, this long sleeve shirt is made from pure cotton and features a fresh mix of the season’s best hues. In the perfect length to layer over henleys and tees or wear tucked into your favorite jeans, this flannel is an instant favorite for fall and beyond.

VEST OF BOTH WORLDS: WEARING A FLANNEL SHIRT WITH A VEST 

WEARING A PLAID SHIRT WITH A VEST

Although you may not always think to wear a plaid shirt when putting together a smart casual look, we’re here to tell you that you absolutely should. First and foremost, let’s establish that “smart casual” is an amalgam of sensible dressing and a relaxed aesthetic, and a surprisingly easy look to achieve. All you have to do is pick the right plaid and style it in an elevated yet comfortable way.  

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Boasting a classic plaid print and an ultra-comfortable, tailored athletic fit, our Pittsboro Flannel Shirt makes a smooth transition from early mornings to late nights. Thanks to its endlessly versatile style and perfect untucked or tucked in length, you can wear this everyday essential with everything - like our MadeFlex Voyager Fleece Vest and Castleton Chino or simple yet sophisticated, tailored black jeans and a leather belt. 

EMBRACE THE CHILL: WEARING A FLANNEL SHIRT WITH A JACKET

WEARING A FLANNEL SHIRT WITH A JACKET

This look has always been one of our favorites because it’s just as practical as a tee and jeans only it’s way more interesting to look at. Using only closet staples to style it, this outfit is super simple yet extremely reliable and always looks good. 

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Designed to do it all, this warm flannel button-front shirt will take your everyday look to new heights. With its tailored athletic fit and perfectly versatile length, our Rosholt Flannel Shirt not only serves as a cozy layer for cooler days but also wears well on its own. Styled here with our Jetson Stretch Twill Jacket and a pair of ultra-comfortable jeans with built-in stretch, this totally timeless transitional outfit is ready for anything that you have planned plus every unexpectedly busy day.   

WEAR WHAT WORKS: WEARING A PLAID SHIRT WITH CHINOS

WEARING A PLAID SHIRT WITH CHINOS

Since we’ve already established plaid shirts as casual, dressing them up may seem like a challenging feat. But the truth is, it’s easy to do and plaid can be worn for work or a dinner date. 

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Endlessly versatile and always in style, our Thaxton Shirt will become an instant favorite. Gauge whether or not you want to tuck your shirt in or leave it untucked depending on where you are heading and the level of formality, then pair with chinos and sturdy lace-up shoes for a look that balances both style and practicality.