Three Ways to Wear a Plaid Shirt

men plaid shirt outfit
PHOTO CREDIT: | Pinterest

The plaid shirt has been around for a good long while, dressing the Scottish highlanders and making an impact on the 90s grunge scene. In this simple guide we’ll show you three ways to wear a plaid shirt and keep you looking your best.

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A plaid shirt has a history that goes back to the Scottish highlands, it’s now become an important classic in nearly every age. Despite its intricate pattern there are ways that you can dress up and down the plaid shirt to create a range of versatile looks. Whether you’re going for a smart look, channeling the 90s grunge vibe, or experimenting with double denim, we’ll show you three ways you can pull off this iconic shirt.

Plaid Shirt Style

Getting this look right needn’t be difficult. It’s a style that you not only see everywhere but it also compliments any outfit, from a suit to a casual pair of jeans. This is without a doubt a low risk option that you can pair with almost anything you already have in your wardrobe, although you’ll want to team it with chinos or jeans that aren’t patterned. If you stick with simple colours, you can be sure you’ll look good in any plaid top you try out.

plaid shirt men levis
SHOP THE LOOK: Dickies | Levi’sRed | Black & White | Navy & Green

Denim with Plaid

You might have seen the denim and plaid look sported from time to time. Think of a big beard, rolled up plaid shirt, a sprinkling of double denim and you’ve got the look down. Of course, if that’s your idea of hell, there are ways to tone it down and create your own style with the variation of colour, design and a few small added details. The look breaks down into two distinct varieties, light and dark shaded denim. The guide below shows off darker denim shades alongside a plaid piece on top. It’s simple and can compliment a casual look so well, with the cap bringing the whole look together.

men plaid shirt outfit carhartt cap
SHOP THE LOOK: DickiesPlaid Shirt | ClarksTrainers | CarharttCap

For a classic look, go with some raw denim jeans in a wide fit, a traditional red plaid shirt, with a denim jacket in the same tone as your jeans and some heavy boots like Dr. Martens. This will give you a super laid back, earthy look, with the plaid shirt breaking up the double denim.

For some variation, try going for a jacket with a few details like sherpa lining, or a distressed design. A slim fit jacket will keep things more eye-catching, but a loose fit will also create its own distinct look, especially when paired with equally loose fitting jeans. Easy ways to experiment with the look can be as basic as different sleeve rolls, the way you cuff your jeans or the colour of your plaid. For a subdued, neutral look go for a blue or black plaid, and for something a little more striking, choose a lighter tone of denim.

men denim jacket outfit
SHOP THE LOOK: EdwinJeans | The Idle ManDenim Jacket


The plaid print has gone through a lot of changes, with various sub-cultures taking it to new areas and styles, making it their uniform, a sign of rebellion or just a way to look good. In its history it’s been worn in various formal styles, and even become part of the royal guards, so it makes sense that you can easily achieve a smart look with a touch of plaid.

You can try out a stylish take on the formal look by pairing a plaid shirt with a plain suit. Mixing too many patterns together will create an awkward clash and take you away from the sleek, smart look you’re trying to achieve, so avoid it at all costs. You can try various colour combinations, but a navy suit is a great base as it goes with a bigger range of colours than black. It also gives a less intense contrast. Try out a slim fit suit and match with a bold plaid print to achieve an interesting look that still maintains a smart feel.

men suit plaid outfit
SHOP THE LOOK: DickiesShirt | The Idle ManBlazer | Dr. MartensShoes

With their casual connotations plaid shirts often come in a thick cotton so that they can easily be layered over T-shirts and vests, but for a formal look try and get one in a thinner material that’s easy to tuck in to your suit trousers. If you’re going for a navy suit with a complimentary plaid shirt, a good pair of shoes to finish off the look would be a brown pair of loafers of brogues, which will give an neutral, put together outfit.

men suit outfit
SHOP THE LOOK: SelectedSuits | RainsBag | HudsonShoes
PHOTO CREDIT: Dappered Threads


Go back to the 90s with a grunge inspired look, taking the casual look to extremes and experimenting with layering and various prints. Because it’s such an iconic look it’s a good idea to try and inject your own personality into the look if you can, otherwise you run the risk of looking like you’re playing dress up.

men plaid shirt outfit
SHOP THE LOOK: SchottJacket | EdwinJeans | GrensonBoots

For a classic 90s look try layering a red plaid shirt over a graphic print T-shirt, adding some lightly ripped jeans to the mix and finishing off with some hightop trainers. Don’t worry too much about colour matching, but try and keep the tones dark, as bright colours aren’t really part of the look.

Distressed jeans and a complex design on your T-Shirt can be enough to elevate your look, so you don’t need to go to extremes to get a interesting vibe. For a cleaner, more slim line version of the look, replace the graphic T-shirt with a plain white crew neck, and swap the ripped jeans for some basic black skinnies. You can also skip the layered look and just wear the shirt buttoned up, creating a ‘smart’ monotone version of the classic grunge style.

men plaid shirt outfit
SHOP THE LOOK: BarbourShirt | Wood WoodJeans | Dr. MartensShoes
PHOTO CREDIT: pinterest

Street Style

We’re taking a look at some people who can wear the shirt right out and about on the streets of the UK. This is probably the most easily accessible way to find out if a style will work on you, although it’s worth being careful of falling into the trap of thinking that because an outfit works for someone else, it’ll automatically work for you. This definitely isn’t the case but you can get a few ideas by comparing different people’s looks and what they decide to do with a particular piece. It can also work the other way and although a look might not work on someone else, it could compliment your build or all round general style.

men plaid shirt outfit
SHOP THE LOOK: StreetstyleLook 1 | Look 2 | Look 3

Further Reading: History

Starting off as a celtic design in the 1500s, the plaid print was worn mostly in the form of a kilt or blanket to protect the wearer from the harsh Highland conditions. Associated with the Scottish rebellion in 1754, it was actually banned and only showed its face again over half a century later. In the 19th century it made its move across the ocean to the US, where company Woolrich Woolen Mills created the iconic buffalo plaid, which they marketed to outdoor professionals like, you guessed it, lumberjacks.

It was the 1970s that helped propel plaid into the mainstream market, with punks mixing the monarch associated print into a vibrant twist of ripped rebellious style clothing. It was also the 70s that saw Vivienne Westwood popularise her iconic plaid designs, which are still a long running and classic style of her work. Of course it was the 90s where plaid took on a more uniformed look, with the grunge movement wearing it as their signature style. This has made a significant effect on the way plaid is styled even today, and is probably one of the most recognisable looks.

men plaid shirt outfit
SHOP THE LOOK: The Idle ManCoat | Jeans | VansTrainers

Today it’s taken on a continued relaxed vibe, worn in various styles, from the traditional grunge look, to a more denim focused, lumberjack style. It’s easy to now take aspects of traditional dress and add a modern twist to it, creating new looks that have an element of history to them.

Quick Guide to Wearing a Plaid Shirt

  • Consider going a little more formal and try it with a suit.
  • Double denim is here to stay so consider mixing the plaid with denim.
  • Go for the grunge look with a lumberjack check plaid shirt over a graphic tee.

On That Note

There are countless ways you can pull off the stylish plaid shirt, but we’ve given you three distinct looks in order to pick and choose what works best for you. One general rule regardless of if you’re going for a smart or casual look is to make sure the colour plaid works for you. With so many choices to go for you can choose a range of looks, from cool and subdued, to bold and bright. The next time you think about picking out a basic neutral shirt, try out a plaid one instead and see what looks you can achieve with one.


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