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Lumberjack Shirt: How to wear it without looking like a lumberjack

lumberjack shirt outfit men
The temperature is dropping and that means it’s time for flannel lumberjack shirts to make their appearance. To help you assemble the best checkered-shirt outfits, we’ve got a bushel of inspiration for you. We cover red lumberjack shirts, green and black checkered, and flannel and wool varieties. My lumberjack look was shot at Scribner’s Lodge in Upstate, NY.

How to Wear a Lumberjack Shirt Without Looking Like a Lumberjack

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Style Advice on How to Wear Your Checked Shirt

You can go for a smart small checked, relaxed wide checked, a hipster lumberjack, or countless other options depending on what look you want to achieve.

With various colors and styles to opt for, it can be a little bit complex to match this piece of clothing with something in your closet. You may also think that this only good for a casual look, but you could easily pull off a smart-casual to classic look when you style it properly.

Below, we will show you a guide on how to wear your checked shirt in a fashionable way.

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3 Styling Checked Shirt Techniques

The Double Shirt

This style is all about layering. You integrate different pieces of clothing to complete one outfit. If you want to add texture and depth to your outfit, you can try wearing two shirts over each other.

You can keep it casual by wearing a T-shirt, a lightweight Oxford or a twill shirt. Keeping your over shirt simple you can most likely add some colors for it.

However, you can always be bold and play with your outfit by wearing some red or brown checked shirts and a plain white Oxford shirt.

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The Smart Casual

Doing a smart-casual style should include at least one blazer and many shirts.

We all know that simple checked shirt become so boring if you don’t mix it up with other clothing. You can find a shirt with perfect cutaway collars and slim-fitting that is made with lightweight cotton to feel more comfortable.

You can pair it with a nice blazer or tuck your shirt in to get that smart-casual get up you wanted.

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The Formal

Most professional men face some difficulties and issues on what to wear on a daily basis. We all know that a well-fitted suit paired with basic white, black or other colored shirts. However, this day in and day out outfit can sometimes be dull even if you add various ties to it. Stripes are a good alternative, but you need something more appealing like a checked shirt and this will be your best option.

When you finally decide to wear checked shirt with suits, flannel plaid is not the best choice. Why? Because it’s too casual. Try to consider some lightweight cotton shirts with small checks like gingham, or larger muted checks like Prince of Wales or windowpane. This type of shirt will be dope.

The best thing to pull off are the shirts with small check patterns that have neutral tones like white or blue. These can match with your solid color ties and will make a contrast with patterns and stripes. Keep in mind that you need to vary pattern sizes.

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Shirts to Shop

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Outfit Ideas

Things to Think About Before Getting A Checked Shirt


The first thing you need to think about when you’re planning to get a checked shirt is the thickness. For Autumn and Winter, a thicker checked shirt is a must. You can wear it buttoned up with a shirt underneath to make you warm.

For Spring and Summer, a cotton checked shirt goes perfectly. Its breathable material will make you feel lightweight and will prevent you from sweating a lot. You can wear it buttoned up or hang open with a short-sleeved T-shirt as a base.


Color is an important thing to take into account, unless you’re opting for a more formal look. A lot of lumberjack styles have bright colors that make it informal because of their noticeable tone.

Combining grey and red will give your outfit a multi-tonal look that is especially great when paired with dark jeans for a casual style. Darker shirts can also be worn with a pair of dark jeans or chinos, some brogue boots, and a coat that will give you a semi-formal look.

Check Style

The third thing you need to consider is the style of the checks you’ll be getting. Checked shirts come in a variety of designs. If you want to go with a small checked shirt, try to pair it with your plain chinos for a more formal look. This outfit will give you a cleaner look and will be perfect for occasions.

Wider checked shirts give you a more casual look that is so easy to pair with skinny or straight jeans. If you don’t want the print to look too busy, you can stick to wearing only two colors. This will give you a more versatile look and it will be easy to mix and match.

Shirts to Shop

Outfit Ideas

Sleeve Length

Sleeve length is so easy to get right. Short sleeved checked shirts are best for Summer. You could pair it with shorts and some slip-on shoes. Though, you could also wear long sleeves in Spring or Summer for a different style.

You don’t need to worry about getting cold since a long sleeved checked shirt has the right length.Make sure that if you opt to shop for a long sleeve, try to make sure you’re shopping for your body type because you don’t want to have a shirt shorter than your wrist, it will make it look you got the wrong size and that wouldn’t look cool.


If you like layering up, you can totally do so. You can layer up your check shirts with a coat, blazer or a jacket. You can go with plain designs so that the clothing won’t compete with the print of your shirt.

You can also put on a lightweight denim jacket for warmer weather. Try to match the tone with your shirt so that they will complement each other. For example, a red checked shirt would go nice with a light denim jacket. If it’s darker shirt, a grey or darker denim would be perfect. A bomber jacket is an awesome alternative too.

For Winter, you can try a thick leather biker jacket over you checked shirt for a more fashionable get up. Finish it with some black skinny jeans and a pair of boots.


Checked shirts also look good in a formal setting, but there’s one question that always comes to mind: What kind of tie should you wear to match the checked shirt? Well, the answer is simple. You can try to wear a fine plain tie. this will give you a sophisticated look. Avoid stripes or graphic design ties since these will clash with your shirt and will not look good.

Keep the tie thin so it won’t compete with the print in your shirt. A good skinny tie would give you an extraordinary look.

More Outfit Ideas

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