Wearing Shoes With Shorts: Outfits and Tips to Nail the Look


Stay cool and stylish.

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The weather’s finally heating up. That means pants and jeans are slowly being replaced by shorts in my wardrobe rotation. From June onwards, I expect to spend most of my time in a t-shirt or summer shirt and shorts because anything else is just too hot.

This is a practical necessity, but it gives me minimal style options. Most days, I just have two basic outfit-related choices to make: what shirt and what shoes to wear with my shorts.

For the latter questions, most of the time I stick with simple sneakers, canvas shoes, or sandals. But it is possible to wear other smarter styles of shoes with shorts.

In this article, I’ll go through some of the best types of shoes to wear with shorts so you can be fully prepared.

Styling Tips for Wearing Shoes and Shorts

  • Many types of shoes go with shorts, the right ones just depend on your outfit.
  • Casual styles like sneakers, sandals, espadrilles, or boat shoes tend to work best with shorts.
  • It’s ok to wear shoes like brogues or loafers with shorts too, just make sure your outfit is equally smart.
  • I like to wear white sports socks with sneakers or canvas shoes, but I avoid them for smarter styles.
  • If you’re feeling really adventurous, try wearing boots with shorts.

The Best Shoes to Wear With Shorts

Canvas Shoes

Canvas shoes are simple, versatile, and go great with shorts. A pair of simple slip-ons like Vans Authentic pair with pretty much any pair of shorts you own, from casual sporty pairs like in the image below to smarter chino shorts. Wear your canvas shoes and shorts with or without socks.

shorts and canvas shoes

Canvas hi-tops also work well with shorts. Again, you probably want to keep your overall outfit pretty casual if you choose this type of shoe. The below image is a great example and the colors of the shoes and the shorts work really well together too.

Shorts and converse hi-tops

Casual Sneakers

The majority of sneakers go well with shorts too, from minimal styles to Jordans and beyond. I personally like to keep my sneakers quite toned down, which means a simple white or off-white leather pair (these Nike Daybreaks are a great example) .

I choose this style because these sneakers go with a wide variety of types of shorts, including some smarter styles.

Shorts and minimalist sneakers

Louder, more in-your-face styles of sneakers work well with shorts too, especially if they have a more relaxed vibe. For example, the chunky sneakers in the outfit below go well with the casual oversized outfit stylings.

Shorts and chunky sneakers

Sandals

If you’re wearing sandals, there’s a high chance you’re also wearing shorts. And this is a look that works really well.

Casual canvas sandals or flip-flops will be fine for the beach, while a high-quality leather pair can go with a wider variety of outfits. I love my Birkenstocks because they are also super comfortable and easy to walk in.

Shorts and Sandals
The Brdwlk

Boat Shoes

Boat shoes are one of the most common types of shoes to wear with shorts. This is for good reasons: they are comfortable, have the right balance of casual and smart, and are good for walking around in.

I also like that boat shoes are easy to find in plenty of colors which makes it possible to find a pair to match your style. I had a pair of brown leather Sperry’s that I wore pretty much all summer one year, but they’re well past their best now.

Espadrilles

Espadrilles and shorts

Espadrilles are perfect for wearing with casual shorts because they are light and cool. I personally wear espadrilles on similar occasions to when I would otherwise wear sandals. Chino shorts, shirts, and t-shirts all with this type of shoe.

Wallabees

Wallabees are a good alternative to the other casual shoes on this list. These are suede or leather shoes with a solid base so they are good for walking around in. And they are the perfect balance between smart and casual to wear with your chino shorts.

I think they look best without socks. Clarks also does a lot of one off versions of the original Wallabees, so it’s easy to be more experimental with your outfits too.

Loafers

Loafers go well with your smarter shorts outfits. While loafers can be super formal, I like to choose more casual styles when wearing shorts. Look for those in unusual colors or with unique patterns, like in the image below.

Check shirt shorts

Dress Shoes

Dress shoes are much more formal than the other shoes on this list. But they can work with shorts (just like they can with jeans) in some very specific situations. For example, you can wear dress shoes with shorts if the rest of your outfit is quite smart.

You could also choose a casual-leaning pair of dress shoes. Give the black patent monk strap shoes a miss and instead go for a pair of brogues in a more adventurous color.

Boots

shorts coat boots

Boots aren’t the easiest shoes to wear with shorts but the look can work if you’re willing to go all in.

The boots in the image above work because the color means they blend into the overall outfit really well. And the long trench coat means the boots don’t look out of place like they would if the rest of the outfit was just shorts and a vest.


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