How to Wear Checked Shirts

Co-authored by Kara Allan

Last Updated: March 6, 2022 References

Checked shirts are a classic wardrobe staple, and they’re great to wear all year long! Pick a short-sleeved lightweight top for the warmer months, transfer to a flannel shirt when the weather gets cold, or pick a nice button-up shirt to wear for more dressy occasions. You can layer the shirt with a jacket or leave it unbuttoned overtop of a T-shirt, making it fit almost any occasion. The bright shades instantly add a nice pop of color to any ensemble, so you don’t need to worry too much about adding colorful accessories, pants, or shoes.

Method 1

Method 1 of 3:

Choosing the Shirt

1
Wear a thin, bright checked top in the spring and summer. For the warmer months, steer clear of heavy, long-sleeved flannel and instead opt for lightweight short-sleeved shirts. Pick brighter colors, like light blue, light green, white, and yellow, for a seasonally-appropriate color theme. For example, pair lightweight chinos with a short-sleeved checked top, and finish off your outfit with a pair of loafers.^{[1]
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- The great thing about checked shirts is that you can find them with long or short sleeves and for whatever season you’re in.
Exploring the Different Styles of Checked Shirts:

Buffalo: One of the more classic styles, two solid-colors with striped checks that intermix with the other squares.

Tartan: Expressive and colorful, often with colored stitching intersecting some of the squares.

Windowpane: Contrasting large white squares paired with a darker material.

Gingham: A tight, neat pattern made of very small squares.^{[2]
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2
Opt for a flannel long-sleeved shirt to stay warm in the cooler months. Browse your local shops or consignment stores to find some checked shirts made of heavier materials that will keep you warm while still making you look good. Try on shirts before you buy them to ensure the sleeve length is long enough and fully covers your wrists—the last thing you need is a too-short sleeve leaving your skin exposed to the cold weather. Pair your heavier flannel with heavier, dark-colored denim for a classic look, and finish off the look with a pair of boots.^{[3]
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- For the colder months, look for a flannel top that is darker and deeper, like reds, blacks, grays, and dark greens.
- If you need a size you can’t find in the store, look online or consider having an ill-fitting shirt tailored. Keep in mind that it’s easier to tailor a shirt that’s too big rather than one that’s too small.
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3
Choose a loose-fitting checked shirt for a casual, laid-back look. Let yourself feel unencumbered as you go throughout your day by choosing a shirt that doesn’t hug tight against your body. Leave it untucked and pair it with a pair of light-washed denim to maintain that casual vibe. Finish off the outfit with a pair of athletic or canvas shoes.^{[4]
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- When going for a casual look, pick a shirt made of a material that doesn’t wrinkle easily, like a blended microfiber shirt.
4
Pick a fitted checked dress shirt for formal events and meetings. Checked shirts don’t have to be confined to casual summer days or cozy winter nights—they’re great options for times when you need to dress up, too! Opt for a more subtle style and color theme for your checked dress shirt to keep it from looking too busy and pair it with a nice suit jacket or blazer to up your style even more. For example, wear a white checked dress shirt with a pair of navy blue slacks; pair the outfit with a navy blue blazer, a pair of dark brown loafers, a dark brown belt, and a tie that matches one of the colors in the checked shirt. Always tuck the shirt in so you look neat.^{[5]
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- Consider pairing your dress shirt with a solid-colored tie that complements the colors in the shirt.^{[6]
  X
  Expert Source
  
  Kara Allan
  Celebrity Stylist, Makeup Artist & Personal Brand Consultant
  Expert Interview. 25 February 2022.} It can add a nice pop of color and really bring your entire outfit together nicely.

Method 2

Method 2 of 3:

Styling the Shirt

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Tuck in your shirt for dressy events to look more put-together. To automatically make your outfit a little more dressed up, go ahead and tuck that shirt into your pants. Tuck in the entire shirt, front and back, making sure to pull the shirt down tight so that it doesn’t poof around your waist. Make sure to wear pants that aren’t stained or ripped, and complete your outfit with a nice pair of loafers or dress shoes.^{[7]
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- For a more feminine look, try just tucking in the front of the shirt. Wear a belt with this look for a nice visual addition.
2
Keep the rest of your outfit subtle so as not to visually overwhelm. Fashion experts across the board agree: when wearing a checked shirt, it’s best to wear neutrally-toned pants and simple shoes and to keep the accessories to a minimum. Otherwise, you risk looking busy. Choose bottoms that are a solid color, like black, white, khaki, forest green, or gray, or stick with classic denim.^{[8]
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Expert Source

Kara Allan
Celebrity Stylist, Makeup Artist & Personal Brand Consultant
Expert Interview. 25 February 2022.} Wear shoes that aren’t bright or multi-colored.^{[9]
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- If you wear a scarf, pick one that is a single-tone rather than one that is patterned. If you can, match the color of the scarf to a color in your shirt; or, pick something that is more muted, like gray, tan, black, or navy.
3
Roll up the sleeves to create a more laid-back vibe. This is a nice option for several reasons: it can help cool you off if you get too warm, and it also adds a nice, effortless look to your ensemble. If your sleeves have buttons on the cuffs, unbutton them first and then roll up each sleeve two to three times. Try to keep the size of the folds equal on each side so they land at the same place.^{[10]
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- You could even roll up the sleeves on a short-sleeved shirt to expose your upper arms and shoulders.
4
Pair your checked shirt with jeans or slacks so you don’t look frumpy. Avoid wearing sweatpants with a checked shirt, especially if you’re wearing flannel. Flannel tops can end up looking like pajama tops if paired with the wrong bottoms. Pick skinny jeans or ones that are a little more form-fitting, rather than baggy pants. For example, pair a red-checked shirt with a pair of black fitted jeans.^{[11]
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- Because checked shirts tend to look a little more casual from the get-go, you just need to be a little more intentional when picking out the rest of your outfit.
5
Add leggings to your ensemble for a comfy yet chic look. When wearing leggings with a checked top, choose a solid color, like black, gray, or forest green. Definitely steer away from patterned or brightly-colored leggings. Wear a checked top that comes down to your upper thighs or lower to create the classic tunic-and-leggings look that is so popular right now. Add a pair of neutral flats, like tan or black, to finish the outfit.^{[12]
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- Keep your accessories to a minimum with this look. Add a watch or a scarf, but avoid adding too many pieces of jewelry so you don’t look too flashy.^{[13]
  X
  Expert Source
  
  Kara Allan
  Celebrity Stylist, Makeup Artist & Personal Brand Consultant
  Expert Interview. 25 February 2022.}
Tip: if you’re worried about your leggings being see-through, wear underwear that is the same color as the leggings, and avoid wearing underwear with patterns or designs on them.

Method 3

Method 3 of 3:

Layering Your Shirt

1
Unbutton your shirt and wear it overtop of a T-shirt for a casual look. Show off a favorite T-shirt, but pick one that isn’t patterned or striped, as the myriad of colors and patterns meshing with the checked shirt could be visually overwhelming. Pick a solid-colored tee, or you could even choose one with words or images on it—just be mindful of how the two tops look when they’re paired together. Wear a pair of cool athletic sneakers to complete this casual look.^{[14]
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- Leave the T-shirt and the checked shirt untucked to maintain your casual vibe.
- Make your outfit look more intentional by matching a color in your checked shirt to a part of your T-shirt’s design, or create a more casual look by not matching the colors.
2
Put a blazer or suit jacket over top of your shirt for a more stylized look. For dressier occasions, look for a fitted jacket or blazer to add to your outfit. Pick a solid-colored jacket and keep the rest of your outfit more neutrally-toned. Button up the blazer or jacket for a more put-together look, or leave it open for a neat, yet slightly more casual, look.^{[15]
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- If your blazer or jacket is bulky and doesn’t fit quite right, take it to a tailor to have it adjusted. This will make you look much neater.
3
Add a jean jacket to your ensemble for a more rustic style. If you’re looking to add a layer of warmth while maintaining a more casual vibe, look no further than a classic jean jacket. Button it up in front, or let it hang open so people can see the contrast between your checked shirt and the jacket.^{[16]
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- Cropped jean jackets look great overtop of longer checked shirts and provide a really nice visual contrast.
- If you’re wearing jeans, try to pick a jean jacket that isn’t the same wash as the jeans.
4
Wear a sweater over your checked shirt in cooler weather to stay warm. Consider wearing a solid-colored sweater, like one that is tan, black, blue, or even something brighter, just as long as it complements the colors in the checked top. If the sleeves on your checked shirt are long enough, pull them down so they peek out of the sweater sleeves, and adjust the shirt collar to be visible and sit overtop of the collar of the sweater. Depending on what style you like, choose a pullover sweater or a cardigan—either option looks nice.^{[17]
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- A checked shirt underneath a sweater will provide a nice pop of color to your ensemble. For a more casual look, choose a baggy sweater. For a classic, preppy style, pick a sweater that is more form fitting.
5
Pop a puffer vest overtop of your checked shirt for a sporty, warm look. This is a nice style for both masculine and feminine looks, and it allows you to completely change the entire feel of your outfit with the addition of just one extra piece of clothing. Because your shirt is checked, pick a solid-colored vest; black, gray, white, tan, and forest green are great shades to choose from. For example, a white checked shirt with a forest green puffer vest will look really nice, especially if the shirt has any lines of green running through it.^{[18]
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- You can zip the vest up for some extra warmth, or leave it undone to show off your shirt underneath.
6
Tie a long-sleeved flannel around your waist for a laid-back vibe. This is a great way to add a checked shirt to your ensemble without having to commit to actually wearing it all day long. It’s especially good for those days that might be warm but also could cool off later in the day, or vice versa. Wear a looser fitting T-shirt that is a solid color, like white, black, or gray. Take an unbuttoned long-sleeved flannel, bring the sleeves around your waist, and create a quick knot to secure the shirt. Wear flats or athletic shoes to complete the look.^{[19]
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- You can pair this look with jeans, black leggings, or shorts.
7
Put on an undershirt no matter what style of top you choose. Because almost all checked shirts button up in the front, it’s a good idea to wear an undershirt so people can’t see your bare skin through the gaps between the buttonholes. This can also help keep you warm, as wind won’t get through to your skin as easily. It also gives you the option to take off your checked shirt if it gets stained or if you get too warm.^{[20]
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- Wear a tank top, T-shirt, or long-sleeved shirt underneath your checked shirt, just depending on the sleeve length and what feels most comfortable to you.
Tip: Pick an undershirt that is neutrally-toned or that complements the colors in your shirt since it most likely will be glimpsed through your top at some point.

Expert Q&A

Question

Are checked shirts fashionable?

Kara Allan
Celebrity Stylist
Kara Allan is a Celebrity Stylist, Makeup Artist, Personal Brand Consultant, and Owner of Style by Kara Allan. With over 19 years of experience, her expertise includes wardrobe styling and edits, personal shopping, personal branding, makeup application, and corporate image consulting. Kara has worked with many celebrity clients including Leonardo di Caprio and Jesse Itzler. She has also been featured in numerous media outlets such as DC Magazine, Washington Post Express, and the Huffington Post. Kara received her training with Stacy London, Former Fashion Editor at Vogue Magazine and Star of TLC's What Not to Wear, and Carla Mathis, Certified Image Master, Association of Image Consultants International.

Kara Allan

Celebrity Stylist

Expert Answer

Yes, they are! All you gotta do is be careful to not overwhelm your whole outfit with other patterns. If you want to wear a checked shirt, look for pieces that complement it, instead of compete with it.
Question

What do you wear with a checkered shirt?

Kara Allan
Celebrity Stylist
Kara Allan is a Celebrity Stylist, Makeup Artist, Personal Brand Consultant, and Owner of Style by Kara Allan. With over 19 years of experience, her expertise includes wardrobe styling and edits, personal shopping, personal branding, makeup application, and corporate image consulting. Kara has worked with many celebrity clients including Leonardo di Caprio and Jesse Itzler. She has also been featured in numerous media outlets such as DC Magazine, Washington Post Express, and the Huffington Post. Kara received her training with Stacy London, Former Fashion Editor at Vogue Magazine and Star of TLC's What Not to Wear, and Carla Mathis, Certified Image Master, Association of Image Consultants International.

Kara Allan

Celebrity Stylist

Expert Answer

Always wear it with other solid pieces so you don't end up being a walking pattern.