Which Men’s Shoes Work Best With Shorts? A Complete Guide

As soon as the summer months roll around, men’s shorts come back into fashion.

When it is sunny, it is time to throw on your shorts and let your legs soak up the sunshine. But putting together an outfit that works can often be tricky.

Which Men’s Shoes Work Best With Shorts? A Complete Guide

For some unknown reason, finding a pair of shoes that works well with your shorts is a lot more tricky than finding shoes to go with a pair of pants.

For some reason, the different colors and fabric just become harder to match together. This can make wearing shorts a little stressful.

Depending on the situation in which you find yourself wearing shorts, it can be a little difficult to find the right shoes for the occasion.

Compiling casual outfits including shorts is usually simple, the difficulty tends to arise when you put together an outfit that is more formal.

In this complete guide, we’ll be taking a look at what men’s shoes work best with shorts.

We’ll also include a guide to coordinating different shoes to the shorts and shirt that you are wearing. So, if you are a man looking for advice on putting together an outfit that includes shorts, keep on reading!

The Importance Of Choosing The Right Shoes

First things first, let’s take a look at the importance of choosing the right shoes for your outfit. Mentally, when you are preparing your outfit, it is really easy to forget all about shoes.

Even when you are trying on clothes to plan which outfits work, it is easy to forget about shoes, simply because you don’t have to wear shoes at home. But shoes really can make or break an outfit.

Even though shoes are only really considered to be an accessory, they are often the most important part of an outfit.

They really do make the difference between an outfit looking smart and an outfit looking incredibly casual.

So wearing the wrong shoe can completely transform the purpose of your outfit. This becomes even more important when the outfit that you are planning includes shorts.

When you are wearing shorts, it is usually your shoes that will make the difference between your outfit being smart or casual, which is why it is so important to get it right.

For example, if you are wearing shorts to a casual beach party, then flip flops will perfectly match the intent of the outfit.

In contrast, if you are wearing shorts to work on a very hot day, a smarter pair of shoes, such as brogues would be much more appropriate.

We have just said that shoes are perhaps the most important part of a shorts outfit, but that doesn’t mean that they should be the center of attention.

The key to a successful outfit that includes shorts is to make sure your shoes do not stand out. Your shoes are an accessory, so they should complement the outfit.

They should never draw attention away from your clothes. With that in mind, let’s dive right in and take a look at some of the best men’s shoes to wear with shorts.

Which Men’s Shoes Work Best With Shorts?

Putting together an outfit that includes men’s shorts isn’t tricky because of a lack of options.

Instead, it is tricky because the shoes that you wear can massively impact the intention of the outfit. There are actually a range of different shoes that work really well with men’s shorts, so let’s take a look at what they are.

Flip Flops

Let’s kick this off with a nice and easy pair of shoes – flip flops.

When you think about wearing shorts, it is likely flip flops that pop into your head, simply because they are the perfect shoes to wear to the beach.

Flip flops scream casual, from the way that they simply slide on and off your feet, to the click clack sound that they make when you walk on a hard surface. Flip flops are the perfect shoes to wear with shorts, as long as you want to look casual.

When you decide to throw on a pair of flip flops, there is so much that you need to consider.

From the length of time for which you will be walking to the health of your feet, to a pair of shoes that you can simply slip on, there are lots of things you need to consider.

This is primarily because flip flops offer absolutely zero support to your feet. So when worn for long periods of time, they can cause the arches of your feet to become painful.

All flip flops do is create a barrier between your foot and the ground’s surface, so if you have any health issues concerning your feet, they won’t be the best choice.

However, flip flops will always be the epitome of casual beach wear. If you are looking for an outfit where you want to look cool, relaxed, and chilled, then these are the best shoes to pop on your feet.

Flip flops are also beneficial during the summer months when the sun is shining and the humidity is high.

With flip flops, you don’t need to worry about your feet getting sweaty and smelly because they are a breathable type of shoe.

They work well with denim shorts, and beach shorts too – making them a first great choice if you want a casual pair of shoes to wear with your shorts.


Sticking to the theme of casual shoes, you should also consider wearing sandals with your shorts. Just like flip flops, sandals are perfect for the warm weather, primarily because they are breathable.

This means that you can wear sandals on a hot day without worrying about your feet becoming sweaty, uncomfortable and smelly. However, when worn incorrectly, sandals can really ruin a good outfit.

One of the worst looks in the entire fashion industry is the combination of socks and sandals. This clothing combination has become the butt of many jokes, and there is no denying that it is an awful look.

Sure, your sandals might be more comfortable when you wear socks, but they definitely don’t look as fashionable. Especially if you are wearing white socks with your sandals.

Even more so than flip flops, sandals scream “chilled”. If you are wearing sandals, it is clear that you are in relaxation mode, and this can really give the wrong impression in some situations.

If you turn up to work wearing sandals with a smart pair of shorts, then you might give your employer the impression that you don’t want to be there.

Likewise if you turn up to a party in a smart-casual outfit wearing sandals, you could offend the people who invited you.

There are only a handful of situations where sandals are an acceptable look. These include beach trips, picnics, and time spent at home in your own garden.

If you are thinking of wearing sandals, make sure that your nails are clean and trimmed. You also want to make sure that your feet have had a good wash to ensure that they don’t smell.

In the right scenario, sandals can really complement a pair of shorts. However, it is important to only wear these sandals in incredibly casual situations, and never to wear them with socks. Especially white socks.


If you want to wear a pair of shoes with your shorts that are mid-way between open and closed shoes, then espadrilles are perfect.

Both sandals and flip flops are completely open, offering insane breathability to your feet, and this is something that a lot of people want during the summer.

However, they are also extremely casual and not appropriate for more formal situations. That is where espadrilles come in.

Espadrilles allow your feet to breathe due to their design, and the fact that you do not have to wear socks with them. But they also offer arch support and comfort that neither flip flops or sandals are able to provide.

They also work well as both indoor and outdoor shoes, so you can wear them when out and about, or you can wear them while shopping or in the office. No matter the situation, espadrilles will work.

That being said, espadrilles aren’t ideal if you plan on wearing them for long periods.

They are designed to be tight to your feet, so over time they can dig in and become uncomfortable. They are designed to be this way to ensure that they do not slip off of your feet while you are walking.

Espadrilles are also designed to have a very thin sole, and this is important for the overall style of the shoe. However, this thin sole does mean that espadrilles are not the best choice if you plan on doing a lot of walking.

In fact, they can actually cause pain to your feet if you wear them for long periods as you will often be able to see the ground’s surface beneath your feet as you work.

However, espadrilles are often a very smart shoe to wear, and they can complement a smart shorts outfit, while also being perfect for the warm weather.

So, in a situation where you won’t be doing a lot of walking, espadrilles will be perfect.

Boat Shoes

If espadrilles aren’t the right look for your outfit, then you should consider boat shoes.

Boat shoes are fairly similar to espadrilles in terms of shape, but they have a number of changes that make them more suitable for certain situations.

For one, boat shoes are considerably smarter than espadrilles.

They generally tend to be made of leather and have little stylish additions that simply make them more suitable for situations where you can’t look casual.

Whether that be a warm day in the office, or a friend’s summer garden party – boat shoes will look incredible.

Boat shoes also have good ventilation, so your feet will be comfortable whenever you wear them.

They have thicker soles which makes them more suitable for walking, and they have fabric that actually absorbs sweat – ensuring that your feet do not become wet and slippy when you are out in the warm weather.

If you are considering investing in a pair of boat shoes, then it is important that you purchase a pair that fits your feet well. You cannot compromise on the fit of boat shoes because they will slip off of your feet.

These shoes are supposed to have a snug fit, so don’t be put off if they are tight in your usual size, they are supposed to fit this way.

You can wear boat shoes in a huge variety of different situations, but they are particularly good in situations where you might find yourself walking on wet and slippery surfaces.

Boat shoes were designed for walking on boats, so if you are ever in a situation where you might encounter water, these are the shoes that you want to be wearing with your shorts.


You probably have plenty of pairs of sneakers at home, and these are always a safe bet when you are throwing together an outfit.

Sneakers go with pretty much anything, and while they can make some formal outfits look casual, they can also make some casual outfits look smarter. The latter applies when you are wearing sneakers with shorts.

Which Men’s Shoes Work Best With Shorts? A Complete Guide

If you throw sneakers on with a suit and tie, then you will make the entire outfit look a lot more casual. In contrast, when you throw sneakers on with a pair of shorts, your outfit will look a lot smarter.

People expect a casual shorts outfit to include sandals or flip flops, so sneakers really do stand out. Especially if you choose to wear canvas sneakers.

Sneakers are one of the few pairs of shoes that you should wear with socks when pairing them with shorts. Without socks, sneakers can become very uncomfortable, so you have to wear socks.

However, we would recommend only wearing shoe liners as your entire outfit could be ruined if you wear anything longer than this.

There are loads of different benefits of wearing sneakers, not only do they look quite smart, but they are quite breathable too.

This style of shoes also offer superior ankle support when compared to the other types of shoes that we have looked at. This means that you can wear sneakers with shorts, and both your feet and ankles will be protected.

When choosing a pair of sneakers to wear with shorts, a white pair of sneakers is always a good idea. White goes with most colors, and it is a bright color, perfect for the warm weather.

White sneakers are sleek and stylish, and they will almost certainly go with your shorts, no matter what color they are.


Finally, brogues tend to work really well with shorts too. Brogues are the traditional men’s dress shoe, which is why they are the shoes you should be reaching for if you want your shorts outfit to look smart.

No matter what color brogues you choose, they are guaranteed to transform your shorts from casual to smart.

There are three different types of brogues: full brogue, half brogue, and quarter brogues.

Full brogues tend to consist of a single color, wear as half and quarter brogues tend to consist of 2 or more colors. These shoes are incredibly stylish, and they can be the perfect way to add additional color to your outfit.

Brogues aren’t the most comfortable of shoes, but in most situations where you have to dress smart, comfort isn’t your top priority.

These shoes are perfect if you want to wear shorts to work, but still look professional. Likewise they are perfect for any summer events or parties where you want to look smart, but still want to wear shorts.

These shoes won’t be suitable for all situations where you are wearing shorts. For example, we would highly recommend not wearing brogues on a hike or to the beach.

However in a situation where you will mainly be indoors, or on a solid surface, they are the perfect option for a smart outfit.

A Guide To Coordination

Now that we have taken a look at some of the best men’s shoes to wear with shorts, let’s take a look at how to coordinate an outfit.

When you are putting together an outfit that includes shorts, there will be 3 different components of that outfit: the shorts, your shirt, and your shoes.

Coordination is key when it comes to planning any outfit, and an outfit that includes shorts is no different. So check out this quick guide to coordination if you want help putting together your outfit.


The first part of any outfit is usually your shirt. Unless you are heading to the beach or your local pool, you will need to wear a shirt when you leave your house.

So, which shirts go best with shorts?

Most of the time, when you are putting together an outfit that includes shorts, you can’t go wrong with a good old polo shirt. The polo shirt offers the perfect balance between smart and casual.

If you wear it with a pair of smart shorts, then it will complement this. Alternatively, if you wear it with a pair of casual shorts, it will work too.

Polo shirts are incredibly complementary, which is why we love them so much.

Alternatively, you also can’t go wrong with a good old button up. If you want a casual outfit, then you could go for a short-sleeved, patterned button up shirt, and it will look great.

Alternatively, if you are looking for a smart outfit that you can wear to the office, a long sleeved button up will look very professional.

To make your outfit look even smarter, simply tuck your shirt in, and you’ll be ready to go.


While the first part of any outfit is your shirt, if you are wearing shorts, then you often have to plan your outfit around these.

Shorts not only differ in terms of style, but they also differ in length and color too.

So there are lots of different decisions to make when choosing a pair of shorts. But no matter what style, length and color you choose, the most important thing is that your shorts fit well.

Most shorts will have a solid color. While you can get multi-colored or patterned shorts, these are usually reserved for swimwear.

So, when you are planning an outfit, you will usually be working with a solid color or material. A lot of shorts tend to be dark in color, but you will occasionally get light denim, white, or beige shorts too.

When choosing a pair of shorts, you have a lot of freedom over the color and style that you buy. Our main piece of advice would be not to buy a pair of shorts that draw attention to the crotch area.

This isn’t a good look, and definitely one that you don’t want to happen in social situations – especially professional ones.

This is why buying shorts that fit well is so important.


Finally, we come to the shoes. As we’ve already spoken about shoes in quite a lot of detail, we’ll keep this short and sweet.

The shoes that you choose can really have a big effect on your outfit, and they can transform an outfit from smart to casual, and vice versa.

Generally, if you are going to a very casual event, we would recommend sticking with an open pair of shoes (flip flops or sandals). Alternatively, if you are going to a formal event, it is best to opt for a pair of closed shoes (sneakers or brogues).


In this guide, we have taken a look at all the different types of men’s shoes that work well with shorts.

So, if you are stuck for choice and don’t know what to wear, you should definitely check out the guide above for inspiration.

Thank you for reading!

Joseph Pais