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What Shoes Go Best with Shorts?

The best way to improve your look is to add a nice shoe to it. This is also true when it comes to shorts. Shorts can always be a challenge because they are not always a good look for the wearer. Find out which shoes are best with sneakers.

A group of people jogging while wearing various shorts and running shoes.

The clothes you wear can be stylish and trendy, but if you make the wrong shoe choice, your outfit is ruined. This is especially true when you wear shorts. Shorts are great when the weather is hot, and you need some ventilation.

While shorts can be cooling and freeing during those hot and humid months, they are not always the most stylish clothing option. This can make your selection challenging, especially if you are the kind of person that only has a few different shoe styles and options in your closet.

Continue reading this article to find out what shoes go best with shorts to make sure you have suitable options in your closet. 

Which Shoes to Wear?


This is a close look at a man wearing ankle-high sneakers with his denim shorts.

Sneakers always seem to be the tried and true option for footwear in many situations. With the right sneaker, you could wear them with just about anything. They are the best choice for the smooth and cool person. You can add them to any women’s shorts or men’s shorts.

You have the classics like Nike, Adidas, Reebok, and Converse. You also have designer shoes by Prada and Coach. No matter what your style, there is a sneaker type and style for you.

They are essential for your wardrobe. When you match them up with shorts, they are cool and ideal for the hot months of summer. You can dress them up with a button-down shirt and even a blazer, and a pair of tailored shorts.

You can switch to business casual by wearing them with polo and chino shorts. Do not forget a t-shirt, sneakers, and just about any type of shorts, including khaki shorts, you want for a completely casual look. 


A woman wearing a pair of brogues with her black short shorts.

Brogues are a stylishly timeless and classic shoe that is common in men’s fashion. These shoes give you a neat and clean look and a touch of uniqueness to your overall look. Brogues come in two main styles, the open-laced Derby and the closed lace Oxford.

A Brogue may also be more commonly referred to as a wingtip. These are commonly thought of as a dress shoe. Do not let this scare you. You can easily match this black shoe (or brown shoes) up with your outfit and look classic.

With these shoes, it is essential to wear the right pair of shorts, but equally important not to wear socks. If you wear socks, it will kill your outfit. 


This is a man in the train station wearing shorts and loafers.

Loafers should be a staple in your closet. If they are not currently, after reading this article, you should get yourself a pair. These slip-on shoes have three basic styles from which you can choose: the Gucci, the tassel, and penny loafers.

Matching up loafers with your chino shorts, light blazer, and shirt will give you the perfect semi-formal summer day event. Loafers are incredibly versatile and can be matched with shorts and a plain t-shirt to give you a casual look. You also want to skip the socks with these shoes.

If you are not a fan of no socks, you can find invisible socks or loafer socks to wear with your shoes. You will not be able to see them, but you will have something between your foot and the shoe. If you want to dress up your tailored shorts, opt for a tassel loafer in velvet or suede. 

Sandals / Flip Flops

A man at the beach wearing khaki shorts and sandals.

Technically, flip-flops are a type of sandal, but many do not consider them as such. When comfort is a must, turn to sandals. They tend to be a simple and affordable shoe that is always popular.

These are a great option for the pool or beach. There are endless style choices in this category. These types of shoes are perfectly paired with Bermuda shorts, denim shorts, and swim shorts.

You can also pair these shoes with short shorts. Flip-flops are always a casual shoe, and you should never wear socks with these shoes. You should be aware that these shoes expose a large part of your foot, including your toes.

Sandals can be a little more dressy than flip-flops. You can dress up your shorts even more with strappy sandals. You should still not wear socks with sandals. 

Boat Shoes

A man relaxing on a sailboat while wearing shorts and boat shoes.

Boat shoes have always been a stylish look and bring a sophisticated look to your outfit. These shoes have always given you a balance of casual comfort to your outfit. They can easily be dressed up or down.

If you need a more formal outfit for an event, pairing them with chinos or tailored shorts is a great way to go. You want to make sure these shoes fit well. Neutral colors are the way to go with these shoes.

Think of beige, tan, or navy. Socks are a consideration for a boat shoe. Either go with no socks or no-show socks. 


A woman wearing a pair of distressed jean shorts with her espadrilles.

Espadrilles are a comfortable shoe that is casual and trendy. They are always an ideal choice for summer. You can easily pair these shoes with chinos or any shoe of your choice.

If you pair these shoes with a stylish shirt or blouse and possibly a blazer, you can create a polished look. You can match them with denim shorts and a polo or other casual top to dress them down slightly for a relaxing weekend look. Espadrilles are usually made from a thicker textile such as canvas.

They do require some breaking in and, once again, leave the socks at home. They should fit snugly when you first get them because they will loosen over time. These shoes conform to your foot. They look great with linen shorts or swim shorts. 

Desert Boots

A man hiking on a mountain trail wearing desert boots.

Desert boots will quickly change the look of your shorts. It takes your outfit from a casual, relaxed look to a more formal style. These shoes are versatile and always in fashion. You can match a desert boot with chinos and a tailored shirt to give you a chic but rugged look.

It might not feel natural to you to combine boots and shorts, but they will make you look stylish. You can even consider ankle boots.


This is a close look at a man wearing a pair of blue tailored shorts and moccasins.

Moccasins tend to be a little less formal than loafers. They are incredibly versatile and not quite as dressy. There are many different types of moccasins.

One style is considered a driving shoe with rubber studs on the bottom of the toe and heel. These slip-on shoes can be worn all year round. Camp moccasins have a bit more structure to them.

They may be referred to as Blucher moccasins and are great for wearing all year long. You can wear moccasins with or without socks depending on the weather and your preference. 


What Shoe is Best with Jean Shorts?

A great shoe choice for jean shorts are sandals. You can also choose to wear sneakers with them. Sandals and flip-flops are great for the summer. Sneakers can be worn at any time of the year.

Can You Wear Socks When Wearing Shorts?

If you are wearing a closed toe shoe, then you want to consider wearing socks. When wearing socks, you might want to consider no show socks, so they can’t be seen. If you are wearing sneakers, you can wear socks that can be seen, but you might want to stay away knee high socks.