Can You Wear High Tops with Shorts? 13 Ways to Style it

The high tops and shorts trend has made a massive comeback from the 80s in recent years. Celebrities have inspired this look, and its ripple effects are seen in millennials. Tread carefully, though, as it is easy to botch this look.

Yes, you can wear high tops with shorts. It’s a great fashion hack, especially if you style them appropriately. It would be best to find suitable shorts length, depending on your height and the length of your legs.

To make sure you understand what this style truly means, read about the epic history of the high tops with shorts trend and learn how to wear high tops.

The History of High-Tops with Shorts

This wasn’t even a trend in the first place. It was initially noted among basketball players in the early 1900s. The high tops provided the players with support for their ankles, thus providing comfort while reducing any risk of injury during the game.

The shoes went on to be advertised by Chuck Taylor, who advertised the Converse company and was featured running around in their brand’s shoes.

Later on, high tops moved to the military as the army wore them during World War Two to help them navigate rough terrain. They have since become a basic necessity for Olympic athletes, and people have adopted the style in their casual wear.

High Tops vs. Low Tops

This article focuses on high-top sneakers, with the most common high-top sneaker brands being Nike, Reebok, and the popular Converse Chuck Taylor sneakers. If you compare high tops vs low tops, you’ll notice that low tops do not reach the ankles, are lighter, and provide less support for the ankles.

High Tops vs. Mids

Mids are a middle ground for high and low-top sneakers. They have a lower collar than high-top shoes. The most common mids are the Jordan 1, and they are less restrictive, making them more comfortable.

Thin vs. Thick High-Tops

As their name suggests, thin high-tops are made of thin fabric material that goes up to the ankles. This shoe type rests on the leg and makes it look smaller than it is. They are not bulky and will feel more like a part of you as you wear them throughout the day.

However, they can be tough to pull off, especially in a hurry. Such high-tops include Converse sneakers and are common among athletes, especially basketball and tennis players.

Thick high-tops are the opposite of thin high-tops. They are made of a much thicker and sturdier fabric that covers up to the ankles. They make your leg look much bigger than its actual size and are bulky to walk around with compared to thin high tops due to their chunkiness.

Thick high-tops brands include Nike, Reebok, and Raf Simons. These brands have gone on to be the best-selling in the sports industries having every sports athlete owning at least a pair of their shoes.

Where to Wear High Tops with Shorts

Amazingly, the look can be worn on many occasions. So where can you wear high-tops with shorts?

  • Everyday casual wear for running errands
  • Gymwear, as many sportswear brands have their lines of high tops and shorts, including GymShark, Nike, and Adidas.
  • Vacation
  • Brunch 

On the downside, you cannot tip the look for the office. Otherwise, high tops with shorts never go out of style and are an excellent add-on to your wardrobe. Invest in different colored high-tops to match the different looks you will put together.

13 Ways to Style Your High Tops with Shorts

Learn how to wear your high tops with shorts with the styles discussed below.

1. With a Plain T-Shirt

high tops with shorts and plain t-shirt for men
Credit: citybeachaustralia on Instagram

This is the most basic yet stylish way to wear high tops and shorts. If your shorts are light-colored, go for a dark-colored T-shirt. This look is ideal for somebody running everyday errands who wants an effortless yet fashion-forward outlook. Try working with different T-shirt types such as round necks. You will not regret it.

2. With a Simple Long-Sleeved Shirt

If you haven’t tried this trend, you are missing out. Pairing high tops and shorts with a brightly-colored, long-sleeved shirt will upscale your look to a whole other level.

You can wear it on summer dinner dates or to the shop, and it can be a fun way to incorporate a bit of formality into your casual day. You can choose a contrasting color for the shorts and shirt.

3. With a Hoodie

If you are going for that bad-boy, skater-dude look, then this is definitely for you. This look never disappoints as it is comfortable and giving. If your bright colored high tops, you can opt for a darker color for your hoodie. Try looking for a slightly oversized hoodie to pull off the look seamlessly.

4. With a Long Cardigan

high tops with cardigan for women

This style is simple and classy. You can choose to go for a sleeved or sleeveless cardigan. Let the cardigan flow right below your shorts. For ladies, opt for a kimono; it will look stylish. This look is embraced by many models whose photos flood social media platforms.

5. With a Hippie Shirt

Hippie shirts are well known to be worn by people who feel the need to express feelings through clothing. They are a great way to match up with your high-tops as it makes them look more hippie-like. Most, if not all, hippie shirts are loose, and this accentuates the look. This look is considered effortless.

6. With a Gingham Shirt

Gingham shirts are simply on another level when paired with high-top shoes and shorts. The shirt can be long or short-sleeved and styled differently to suit the outfit. They can be worn as a cover-up or simply as they are.

For instance, if you use a cover-up, let your inner top be the same color as your high-top. Always choose a brightly colored gingham shirt, which can significantly elevate your look.

7. With a Denim Jacket

You can never go wrong with a denim jacket, especially black denim. This look is lazy and casual but highly fashion-forward. If possible, try to rock a similar colored denim jacket to that of your high tops.

8. With a Pajama-Style Shirt

high tops with pajama style shirt for women

This look is a guaranteed hit. It is effortless yet so chic. Experiment with different styling techniques using the blouse and watch the magic happen. This trend is seen in celebrities in the streets.

9. With a Shorts Suit

This fashion style speaks sophistication through and through. The look offers formality and functionality. The shorts, suit, and high-tops look has gained its fair share of fans on social media platforms that show how to style converse high-tops.

If you have a dark-colored suit, opt for a brightly-colored high-top and vice versa.

10. With Striped Shirts

Striped shirts often give a geek, wealthy billionaire, player, having it together vibe. They are not very much liked but are slowly crawling back to closets due to the different ways you can use to style them up.

A good example is the matching of striped shirts with high tops and shorts. This look is great for the summertime and is attracting attention in the fashion world.

11. With a White Top

White tops are simply the best and should never lack in anyone’s wardrobe. They are easy to style as they go with almost every casual look, including high tops and shorts. You can simply tuck the top in, wear it loose, crop it, or form a knot. The choice is yours and is bound to turn out great any way you do it.

12. With a Peasant Shirt

Peasant shirts can be hard to style, yet this is the ultimate look to style up with high tops and shorts. The look is simple and does not attract a lot of attention to you. This look is, however, deemed for older women, which is a disputable factor as major Hollywood stars are spotted wearing it. The style goes great with all forms of jewelry.

13. With Accessories

styling high tops with sunglasses and a chain

That’s right! Accessories will make any dull cloth pairing look like a match made in heaven. Adding sunglasses, a watch, and a chain can make high tops and shorts not so dull a look. Do not overdo it, though, as too many accessories make you look like a joke.

Basic Dos of Wearing High-Tops

  • High tops and high-waist shorts. This look is perfect for short people who wish to get the feel of having longer legs and a more slender body. This fashion trend has received hate among teens due to rising names such as “mom jeans.”
  • Pair your high tops and shorts with a loose shirt. It gives off a chic feel.
  • Have fitted shorts on. That’s right! Well-fitted shorts show off your physique and are easy on the eyes.
  • Pair thin high-tops with dressier shorts, while thick high-tops pair better with sporty shorts. It does not exhibit any functionality aspect during sporty activities, and one may change things for comfort and functionality.
  • Always wear clean, high-top sneakers. Converse sneakers can be machine-washed and dried. It is convenient as you will not need to spend time scrubbing them clean. Remember that they can shrink if not washed according to instructions, so be careful.
  • Your high tops need to match your top and contrast with your shorts. This basic rule of thumb for high-tops must be kept sacred.

Basic Don’ts When Wearing High Tops

  • Wearing the same color of shorts with Converse high-tops is taboo. However, this rule does not apply to the color black, a classic duo.
  • High tops and baggy pants are a no-go, especially for the male gender. People may judge you as clumsy-looking and untidy instead of the fashionista vibe. Instead, pair your high tops with straight pants or skinny jeans.
  • Do high tops make you look shorter? Yes, especially when worn with long socks. This look also makes you look backward and shows that you are trying too hard. This only works for cheerleaders. It doesn’t mean you shouldn’t wear your high-tops with socks. Socks are recommended as they can prevent blisters on your legs.

Final Thoughts

High tops are very reliable shoes to wear with shorts and are a classic look for different age groups. They are widespread among teens and people in their twenties. They are also common among athletes, especially in basketball games, tennis players, and golf players.

High tops are a great add-on to your shoe collection as you can pair them with jeans, dresses, and shorts.

Have you tried this look? Let me know your thoughts on it in the comment section below.

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