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How To Wear A Long Sleeve Shirt With Shorts

Long sleeve button-ups are generally more formal than casual, but they can be worn casually, too. Shorts are naturally incredibly casual items. The question is, can you wear a long sleeve shirt with shorts?

Wearing a long sleeve shirt with shorts is possible. Rolling up your sleeves is recommended, and layering your shirt looks great. Longer shorts are your best option, but most shorts styles work. Collarless shirts reinforce and enhance the casual look of the outfit.  

This post will give you some tips on how to wear a long sleeve with shirts, as well as go through some frequently asked questions at the end.

long sleeve shirt with shorts and hat
Image From Deposit Photos

6 Tips For Wearing Long Sleeve Shirts With Shorts

Here are some tips to help you pull off a long sleeve with shorts every time. 

1. Roll Up Your Sleeves

Wearing a long sleeve shirt with shorts can look pretty odd if not done properly.

There is a lot of contrast between shorts and a long sleeve shirt. The weather is one of these.

Typically shorts are only really appropriate for casual outfits in warm weather. 

Conversely, long sleeve shirts are appropriate for a variety of formality levels and are best for cooler weather if worn casually.

This means that, when worn together, the combination can appear poor put-together.

A solid way to somewhat alleviate this mismatch is to roll up the sleeves of your long sleeve shirt.

untucked denim shirt with shorts
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While, at first glance, doing so might seem to defeat the purpose of wearing a long sleeve shirt, rolling up your sleeves actually adds to the outfit’s aesthetic.

Wearing a long sleeve shirt whose sleeves are rolled up creates a much more laid-back, casual vibe.

If wearing your long sleeve shirt as an overlayer, it’s important to ensure that your underlayer’s sleeves cannot be seen when rolling up your shirt’s sleeves.

This can be done by either rolling up your underlayer’s sleeves or wearing a short-sleeve underlayer.

2. Layer Your Shirt

Layering your shirt can be a great way to add some flair to your outfit without being overly flamboyant.

The term “layering” simply means wearing one garment over another. In this case, by wearing your long sleeve shirt over another item of clothing, such as a T-shirt.

There are several factors to consider when layering your clothing: color, texture, patterns, and types of clothing.

When wearing a long sleeve shirt, the best way to layer it is incredibly straightforward and easy to pull off.

Simply wear your button-up, long sleeve shirt over a plain white T-shirt – making sure you keep your long sleeve shirt completely unbuttoned.

Not only will this create a fantastic look, but it’ll allow you to experiment with the colors and patterns of your overlayer shirt due to both the versatility of a white T-shirt and the casual vibe of the outfit.

This layered look works particularly well with shorts as it contributes to the outfit’s casual nature.

Furthermore, layering clothing well demonstrates knowledge and understanding of when and how to wear particular clothes and clothing combinations.

Layering your shirt isn’t imperative to success in wearing a long sleeve shirt with shorts, but it certainly helps.

denim shirt overlayer with shorts
Image From Deposit Photos

3. Think About Shorts Style

When wearing a long sleeve shirt with shorts, it’s important to think about the style of your shorts. This includes the type of shorts as well as the length and color.

Choosing the wrong shorts can be detrimental to your outfit, so your shorts choice should be carefully considered.

While most shorts styles are acceptable, from casual cargo shorts to the slightly-more-formal chino shorts, there are still a few you should avoid.

Biker shorts, for example, should be avoided. They are designed as sports apparel and should be kept solely for sporting endeavors.

Similarly, it’s best to steer clear of board shorts. While they can be worn with some casual outfits, it’s best to avoid them with a long sleeve shirt.

As for the color of your shorts, that heavily depends on your shirt color. 

However, a couple of safe shorts colors are navy and khaki, as these go with pretty much anything.

Both are neutral colors and are renowned for being incredibly versatile and pairing with most colors nicely.

Finally, the length of your shorts is an important factor. Short shorts will look disproportionate to your long sleeve shirt.

Therefore, when wearing a long sleeve shirt with shorts, go for longer shorts – those that reach just above knee length are ideal.

4. Consider A Collarless Shirt

Because of its casualness, his outfit is pretty lenient with regard to the different styles, colors, and patterns you can wear.

If you wish to enhance this casualness, one way to do it is by ditching the collar of your button-up, long sleeve shirt.

Collarless shirts are becoming increasingly popular and are a great way to wear a button-up without the formality of a collar.

This decreased formality means that collarless shirts go particularly well with shorts, as shorts are also very casual in nature.

The same guidelines apply to wearing a collared long sleeve shirt. In fact, collarless shirts can be even better for layering than collared shirts

5. Shirt Color Matters

While shirt color is quite an important element to wearing a long sleeve shirt with shorts, there is a lot of room for experimentation.

This is because, as mentioned, the best shorts colors are navy and khaki; pretty much any shirt color will work with these versatile, neutral colors.

Colors that work particularly well, however, include off-white, olive green, and navy.

Image From Deposit Photos

As well as colors, patterns can look incredibly good on a long sleeve shirt with shorts.

Whether you go for more discreet, subtle patterns or bolder ones, the effect on your outfit will remain the same: extra flair and personality.

If wearing your long sleeve shirt as an overlayer, a checkered-patterned shirt will look especially good. 

6. Keep It For Casual Situations

Wearing clothes of an inappropriate formality level can be seen as disrespectful or rude.

Because of this, it’s important to ensure that you know when and where to wear particular outfits.

This outfit is incredibly casual and, therefore, should be treated as such.

Keep in mind that, while it could be mistaken for smart-casual wear in warmer climates, this outfit is strictly casual.

Shorts alone are too casual for pretty much any situation of as little as slight formality.

Combining shorts with the contrast of a long sleeve shirt means that, overall, the look is only appropriate for casual outings.

The casual nature of this outfit means that it’s possible to accessorize more than usual with jewelry, a watch, or similar.

Furthermore, you should avoid any formalwear with this outfit – particularly dress shoes, and these would create a significant formality mismatch.

Frequently Asked Questions

Now that you know how to wear a long sleeve shirt with shorts, here are some frequently asked questions to round off the topic.

Can You Wear A Long Sleeve Shirt With Biker Shorts?

It’s best to avoid wearing a long sleeve shirt with biker shorts. Biker shorts are designed for sporting endeavors and should be worn as such. They simply don’t look good with a long sleeve shirt.

While most shorts will work with a long sleeve shirt, biker shorts are one of the few shorts styles that don’t.

They should be kept solely for sporting activities – never venturing outside this realm.

Can You Wear A Long Sleeve Shirt With Khaki Shorts?

Khaki shorts look fantastic with a long sleeve shirt. Khaki is a neutral color, allowing for a wide range of possible shirt colors and patterns. Make sure that your khaki shorts aren’t too short – reaching just above knee height is ideal.

Khaki shorts are one of the best options to wear with a long sleeve shirt. 

They are versatile and, therefore, work with most long sleeve shirts. 

It’s important to ensure that your khaki shorts aren’t too short, as this could ruin the look.


Best kept for casual situations, this outfit can look fantastic when done correctly. Getting it right takes practice, but it’s worth the time spent perfecting it.