How To Wear Checkered Shorts: 15 Chic Outfit Ideas For Ladies

In the world of fashion, there’s a type of shorts that stands out from the crowd – literally. Checkered shorts are a stylish and chic option that can elevate your look in an instant. But what sets them apart from other types of shorts? For starters, checkered shorts aren’t just a simple plaid pattern. Instead, they typically feature black and white squares of uniform size, creating a classic and timeless design.

While they may present a slightly greater styling challenge than denim or cargo shorts, it’s definitely not an insurmountable task. To help make things easier for you, I’ve curated some great options and will be sharing them with you next.

Checkered Shorts with Black T Shirt

Checkered Shorts with Black T Shirt
Photo Credit: thechrisellefactor

Kick-starting our list of stylish and casual outfit ideas is a laid-back ensemble that’s perfect for everyday wear. To create this effortless look, start by pairing a classic black T-shirt with a pair of checkered shorts. Add some comfort to your feet with a pair of black slide sandals and complement the overall aesthetic with a bright yellow leather purse – the pop of color adds an instant touch of sophistication.

Black Sleeveless Top with High Waisted Checkered Shorts

Black Sleeveless Top with High Waisted Checkered Shorts
Photo Credit: pinterest

To achieve a sophisticated and elegant appearance, consider pairing a sleek black sleeveless top with high-waisted checkered shorts that create a visually elongating effect by drawing attention upwards. For an added touch of femininity and a slimming influence, complete the look with pink high heels. This harmonious combination will not only elevate your style but also make you appear taller and more slender.

Checkered Shorts with White Blazer

Checkered Shorts with White Blazer
Photo Credit: allteenstalk

A refreshing take on the traditional work outfit is presented through the harmonious combination of black and white checkered shorts, where a sleek black crew neck blouse serves as the perfect accompaniment to a crisp white blazer. To elevate this ensemble, complement the upper attire with the same checkered shorts, accompanied by a pair of striking black strappy open-toe heels that exude sophistication and glamour.

Wear with White Blazer & Black V Neck Tee

Wear with White Blazer & Black V Neck Tee
Photo Credit: worldoffemale

For a more relaxed take on the classic workwear look, consider pairing checkered shorts with a stylish combination of a black V-neck T-shirt and a white blazer. To add some extra edge, top off the outfit with black suede shorts boots. The result is a unique and captivating business casual ensemble that’s sure to turn heads.

Grey Crew Neck T Shirt with Mini Checkered Shorts

Grey Crew Neck T Shirt with Mini Checkered Shorts
Photo Credit: allteenstalk

In contrast, let’s shift our attention to a laid-back ensemble that embodies effortless chic. To recreate this look, start with a grey t-shirt featuring a sleek black neckline. Pair it with a pair of short checkered shorts and finish the outfit with a pair of black flip-flops. This casual yet put-together combination is perfect for those days when you just want to run errands or casually visit a friend’s home.

Blue and White Striped Button Up Shirt with Checkered Shorts

Blue and White Striped Button Up Shirt with Checkered Shorts
Photo Credit: People

To create a stylish business casual ensemble with a unisex twist, consider pairing a blue and white striped button-down shirt with black and white checkered shorts. The combination of these two pieces will provide a strong foundation for the outfit. To add a touch of femininity and a dash of elegance, slip on a pair of pale pink ballet flats. For a more polished finish, carry a pink clutch bag that adds a hint of sophistication to the overall look.

White Mock Neck Blouse with Checkered Shorts

White Mock Neck Blouse with Checkered Shorts
Photo Credit: glamradar

Elegance is just a few pieces away. For a stunning feminine look, start with a crisp white mock neck blouse featuring delicate lace details. Pair it with checkered shorts for a playful touch. Elevate your outfit with a pair of black pointed toe heels that exude sophistication. To add a pop of color and inject some whimsy into the overall aesthetic, carry a vibrant white and yellow floral printed purse.

White Spaghetti Strap Tube Top with High Waisted Shorts

White Spaghetti Strap Tube Top with High Waisted Shorts
Photo Credit: gojane

Elevate your style by highlighting your slim waistline and long legs with this effortless yet chic outfit, perfect for those in great physical shape. To create this look, start with a classic white tube top featuring spaghetti straps that draw attention to your toned midsection. Pair it with high-waisted black and white checkered shorts that skim the body elegantly. Finally, add a refreshing touch with a pair of white sandals, allowing you to showcase your legs in their full glory.

Navy Camisole with Mini Shorts

Navy Camisole with Mini Shorts
Photo Credit: dailymail

While the majority of people opt for plain t-shirts and denim shorts during the summer months, this unique combination is sure to make you stand out from the crowd. To achieve a truly eye-catching look, consider pairing a navy blue camisole with a double strap design alongside high-waisted mini checkered shorts that will create a striking contrast and give the illusion of being taller and leaner.

Complete the outfit by adding a touch of bohemian flair with nude heeled sandals, perfect for those who dare to be different.

Checkered Shorts with Blush Pink Cold Shoulder Blouse & Embroidered Leather Jacket

Checkered Shorts with Blush Pink Cold Shoulder Blouse & Embroidered Leather Jacket
Photo Credit: pinterest

This striking ensemble stands out for its unique blend of creativity and sophistication. To achieve this look, start by pairing a blush pink cold shoulder long sleeve blouse with a statement piece – a black embroidered leather jacket. Add some visual interest to your lower half with high-waisted checkered shorts in a bold black and white combination, before finishing the outfit off with a pair of sleek black ballet flats.

White Chiffon T Shirt with Checkered Mini Shorts

White Chiffon T Shirt with Checkered Mini Shorts
Photo Credit: bekleidet

In this outfit, the fabric plays a significant role in elevating its overall appeal. The pairing of a delicate white chiffon top with checkered mini shorts may seem straightforward, but it’s the tee’s texture that adds an air of sophistication. To complete the look, add pale pink heels and a pink leather shoulder bag, which work together to create a charming and inviting ensemble.

Wear with Royal Blue Cropped Halter Top

Wear with Royal Blue Cropped Halter Top
Photo Credit: fashionablykay

Elevate your style by incorporating a pop of royal blue into your ensemble. To create an eye-catching and energetic look, consider pairing a cropped halter top in this vibrant hue with high-waisted checkered shorts. The pièce de résistance is completing the outfit with royal blue ballet heels that harmoniously match the tone of the top.

Black Three Quarter Sleeve Tee with Checkered Shorts

Black Three Quarter Sleeve Tee with Checkered Shorts
Photo Credit: lookbook

Elevate your style with this playful ensemble that’s sure to turn heads. Start by pairing a black three-quarter sleeve t-shirt with checkered shorts – the perfect combination of comfort and fashion. Add some height and sophistication with black ballet heels, then top it all off with a bold red baseball cap for a boyish touch that’s both stylish and eye-catching.

This outfit idea is perfect for those looking to mix things up from their usual denim shorts routine and add some variety to their summer and spring wardrobe.

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