From the Court To the Streets: High Tops with Shorts

by jacky chou
Updated on

Summer is the best time to experiment with new and exciting fashion trends, so don’t miss out on the high tops with shorts trend!

High-top sneakers are a fun and stylish footwear option that adds personality and flair to any outfit. However, figuring out how to wear these shoes with shorts can be challenging. So, we will provide you with nine unique and creative ways to wear your sneakers with shorts and rock this trend with confidence and style.

But first;

What Are High Tops?

High-Top Sneakers

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High tops are athletic shoes with a higher cut around the ankle than standard sneakers. They were originally designed as basketball shoes to provide additional support and protection to players’ ankles during games. In addition to being a staple in the world of basketball, high-top sneakers are popular lifestyle shoes. As the fashion world becomes increasingly comfort-oriented, you want to jump in on the sneaker trend to experiment.

Besides high-top sneakers being fashionable, they also have practical benefits for foot health. The higher cut around the ankle can provide additional support and stability, especially for individuals with weak or unstable ankles. While there is uncertainty if high-top basketball sneakers are safer than low-cut sneakers, high tops are comfortable and supportive for casual wear when running errands.

9 Ways to Wear High-Top Sneakers with Shorts

9 Ways to Wear High-Top Sneakers with Shorts

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High-top sneakers are a versatile footwear option for various outfits, including shorts. You’re in luck if you’re wondering how to wear high-tops with shorts as a man. Here are nine styles to rock today.

1. Go Sporty and Casual

Go Sporty and Casual

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Have your high-top sneakers, athletic shorts, and a fitted t-shirt? Why not pair these to show your casual side? This look is ideal for your errand day or the gym.

Ensure your shorts and shirt fit well without being too tight or loose and opt for breathable fabrics like cotton or moisture-wicking materials if you plan to be active in this outfit. Then, ensure your sneakers have good cushioning and support, especially if you plan to be on your feet for an extended period. Avoid sneakers with too many embellishments or flashy colors if you prefer a more understated look.

You can add accessories like a baseball cap or sunglasses to complete the sporty and casual look. Keep your accessories simple and functional, and avoid anything too flashy or ornate.

2. Pair Your High-Top Sneaker with Denim Shorts

Pair Your High-Top Sneaker with Denim Shorts

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If you want a casual yet stylish look, pair your high-top sneakers with denim shorts and a button-down shirt. Denim shorts are versatile and can be dressed up or down depending on the occasion. Choose a fitted shirt for a cohesive look.

Then, ensure your sneakers complement the entire look, so choose the style and color carefully. For example, consider a pair of white or black sneakers for a classic look that goes well with denim.

To accessorize your denim shorts look, you can add a watch, a leather bracelet, or a pair of aviator sunglasses. These accessories will add a touch of sophistication and style to your outfit. Remember that denim shorts look best when not too baggy or tight, so choose a pair that flatters your body shape.

3. Go Rugged with Cargo Shorts

Go Rugged with Cargo Shorts

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You can pair your high-top sneakers with cargo shorts and a graphic tee for a rugged and casual look. Cargo shorts are a great option for their utilitarian pockets and relaxed fit. Pick a graphic tee to complement your cargo shorts or a tee with a fun design that reflects your style.

If you don’t want to wear boots to a hike, consider a pair of brown or olive green high-top sneakers for a natural look that goes well with shorts. Look for sneakers with good traction and durability, especially if you plan to wear them in rough terrain. You can add a canvas belt, a military-inspired watch, or a baseball cap to complete the look.

4. Look Classic Cool with Chino Shorts

Look Classic Cool With Chino Shorts

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Just like when wearing chino pants, you want to pair your shorts with a classy polo shirt. Chino shorts are a dressier option for various settings, like very formal events or a night out with friends. Choose a polo shirt that complements the color of your shorts for a cohesive and polished look. Remember, these shorts look best when they hit just above the knee and have a tailored fit.

Then, pair the look with black or navy sneakers for a sophisticated look. In addition, ensure the sneakers have a sleek design and are made with good-quality materials to elevate your outfit. You can add a touch of elegance and refinement to this look with a pair of classic sunglasses, a leather belt, and a dress watch.

5. Rock a Summer Look with Swim Shorts

Rock a Summer Look with Swim Shorts

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Pair your high-top sneakers with swim shorts and a t-shirt or beach shirt for a relaxed, beach-ready look. Ensure your t-shirt or beach shirt complements the color and design of your swim shorts for the best look.

Then, consider a pair of brightly colored or patterned sneakers for the style. For example, white sneakers go well with many swim shorts. However, ensure they are water-resistant or quick-drying, especially if you plan to spend the day near the water.

You can wear aviator sunglasses and a hat or baseball cap for a touch of elegance. These accessories add to the laid-back and carefree vibe of the outfit.

6. Nail the Street Look with Baggy Shorts

Nail the Street Look with Baggy Shorts

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Wearing baggy shorts with high-top sneakers is a popular streetwear look that combines comfort and style. The shorts are a relaxed and casual option for different settings, from a day at the park to a music festival.

But, since anyone can rock this look, you can stand out by pairing your shorts with unique, eye-catching pieces like oversized vests, shirts, hoodies, or denim jackets. Then, choose high-top sneakers that make a statement, like a dark Christian Louboutin, to add a touch of luxury and glamour to your outfit.

When styling your shorts, think outside the box and experiment with unexpected combinations. For example, pair an oversized vest or hoodie with a fitted t-shirt for a balanced silhouette. Alternatively, layer a graphic t-shirt or button-up shirt over your baggy shorts for a more relaxed and carefree vibe.

Accessorize your look with unique and unconventional pieces like statement jewelry, a bold hat, or colorful socks to create an eclectic look.

7. Create a Monochromatic Look

Create A Monochromatic Look

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If you want a simple, minimalistic, yet classic look, you can create a monochromatic outfit by pairing your high-top sneakers with shorts and a shirt in the same color family. Monochromatic outfits are stylish and sophisticated, creating a streamlined and cohesive look. However, you want to choose a color that complements your skin tone and personal style.

When selecting high-top sneakers, choose from various colors and textures to create the best monochromatic look. It is important to wear sneakers with a similar texture or finish to your shorts and shirt for a cohesive and polished look. 

Then, accessorize your monochromatic look with subtle and understated pieces like a simple necklace, a leather watch, or a fedora hat. These accessories will refine your look without detracting from the monochromatic style.

8. Rock Your High Tops with Shorts and a Knitted Hoodie

Rock Your High Tops with Shorts and a Knitted Hoodie

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If you aim for a cozy and comfortable look, pair your high-top sneakers with a knitted hoodie and shorts. This outfit is perfect for a casual day out or a relaxing weekend at home. The knitted hoodie will keep you warm and comfortable, while the shorts and high-top sneakers will give you a laid-back and stylish look.

Wear a pair of neutral-colored sneakers like black or grey for a subtle and understated look or a brighter color like white, red, or blue for a pop of color that will stand out. Complete the look with conspicuous socks and accessories like a beanie hat.

9. Look Edgy with Jogger Shorts and a Denim Jacket

Look Edgy with Jogger Shorts and a Denim Jacket

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You can pair your high-top sneakers with jogger shorts and a denim jacket for a stylish, edgy, off-duty outfit. The jogger shorts will give you a comfortable and relaxed look, while the denim jacket will add a touch of ruggedness and style. This outfit is ideal for a night out with friends or a casual day around town.

Consider a high-top sneaker with a sleek and modern design for a contemporary edge or a more classic and timeless black or white pair for a casual style. Sophisticate your look with a statement watch or a chain necklace.


As you can see, high-top sneakers and shorts make for a versatile and trendy combination that adds personality and flair to your summer wardrobe. Whether you prefer a sporty and casual look or a more refined and polished style, there are endless ways to wear high-top sneakers with shorts. From tailored shorts to joggers and swim shorts, we have shown you nine outfit ideas to inspire your next summer look. With these ideas, we hope you feel confident and stylish in your next summer outfit.

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jacky chou


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