How to Combine Boots with Shorts – 2024 Online Style Advice

We all love boots, don’t we? It doesn’t matter if you are a man or woman; at least one pair of boots will be on your shelves.

There are several different reasons why people like to wear boots. However, it seems that there are two most common ones. First of all, the boots are comfortable and practical. You can wear them in many cases. Despite that, they can also be stylish and versatile. More precisely, people can feel comfortable and look nice at the same moment.

Purchasing a new pair of shoes is always a complicated process. You see hundreds of models designed by different brands and it is difficult to decide on one. Yet, the experts from Online Stylist say that the problem starts to become even bigger when you need to adjust them to your outfit.

It is not a secret that boots can’t go with all the outfits. Things are especially tough when you want to combine boots with shorts. We can say that this is truly a tricky game.

We know how tough this decision can be. Yet, we would want to give you a couple of advice that will make the entire process easier.

Let’s get started.

Shorts History

Why would anyone need to know the history of this piece of clothes? Well, the reason for that is simple. You will understand which purpose shorts have. We will give you pieces of advice for this year. However, our goal is to teach you something new. You can dress under our “instructions”, but next year, you will have the same problem. Trends in the world are changing rapidly.

So, shorts originated as a part of school prep for children. The history starts in the early 1880s. At that moment, that was the only purpose of this item. Yet, in the coming decades, things have changed. Men slowly started to adapt their shorts to their boots. That’s why you can see many pictures of soldiers during WWI I WWII wearing shorts combined with combat boots. After the war ended, fashion designers brought a new trend to the world.

The Best Time for Wearing Boots & Shorts Combination

Okay, there is one obvious moment when you should wear this combination. If you like hiking, then wearing your shorts with hiking boots is the perfect match. However, at that moment, you are not thinking about style and fashion. When you are not hiking, there are two different rules that you need to follow.

First of all, the temperature outside should be hot. This means that this combination is perfect within the summer. This especially includes the period from early June to late August. Of course, you need to adapt to your environment as well. We can use the Bermuda area as an example. People there wear shorts with a blazer and a jacket. So, do not try to be creating a lot. That doesn’t make you a trendsetter.

Despite that, this combination is not good for some formal events. For example, if you have a business meeting, then wearing something like this would look silly. Instead, you should rather choose to wear trousers.

So, after we explained these two important things, let’s get to the point. There are a couple of types of boots that go together with shorts. Still, that doesn’t mean you can wear them in the same way.

How to Combine Ankle Boots with Shorts


Indeed, ankle-length boots are one of the most versatile types of boots. Logically, this especially counts when we talk about men. Their minimal appearance is their main advantage. They can go together with different types of outfits. This even includes the smart-casual looks. People have a problem adjusting to this sort of outfit because it is a bit complex.

Anyway, pairing these two things has some rules. First of all, you need to pick the right boot style. We have two different options to suggest. For example, Chelsea ankle boots are an easy and sleek option. However, Chukkas and similar lace-up styles can also be a good match. Anyway, we do not know which style you exactly prefer. Because of that, we will leave this decision to you.

Anyway, after picking the pair of boots, we recommend you pair them with shorts and a button-up shirt. Despite that, a good match would be a combination with a roll-neck sweater.

For instance, Chelsea boots are suitable with a brown or suede pair. Still, there is also one more alternative that you should use. Pick the black or burgundy leather Chelsea boots and math them with a short-suit. This will make you look more attractive during the spring months.

How to Combine Lace-Up Boots with Shorts

Well, people that are felling tough will look for some specific solutions. In this case, we suggest you add a pair of combat boots to your outfit. This means that you should add classic boots to your shelves at home. When you look closer, they look similar to those that soldiers were wearing during the WWI and WWII.

So, who should use this combination?

Of course, we do not want to say that everyone will like this style. However, if you are a big fan of casual outfits, then this would be a perfect choice for you.

There is one specific moment when this combination would suit perfectly. If you are a fan of weekend outings, then you can wear this combination while you are at the party. They even look better when you match them with other edgy designs.

It is recommended to stick to the dark color palette. Despite that, we suggest you opt for heavy-duty fabrics. For example, leather and denim would be a great choice.

How to Combine Desert Boots with Shorts

We already mentioned Chukkas boots before. They are well-known as the casual pieces of cloths just like shorts. The combination of these two things offers a unique aesthetic that other shoes cannot offer. You won’t be able to find a footwear collection that doesn’t contain this sort of shoes. This especially counts when we talk about men. Because of that, we can easily say this is a trend in 2024 as well.

Anyway, our suggestion is to match these boots with chino shorts and a tailored shirt. This will give you a modern look. If the weather is a bit cold, we suggest you throw on a light jacket or sweater.

So, which of these combinations seems the best for you? We would like to hear you!

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