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The Best Shoes You Can Wear With Shorts This Summer (And Look Stylish)

Men's Style Guides
Monday, 5th August, 2019

What Shoes To Wear With Shorts

If you’re thinking of wearing shorts this season, you’ll be wondering one thing:

What shoes should I wear with shorts?

There’s a ton of footwear options out there, and you’ll want to pair your shorts up with the right pair of shoes. It’s an item which should never go overlooked, there’s a lot you can tell from a man’s shoes.

Often, especially with the ladies, they’re one of the first impressions you can give someone.

It can be difficult to find the right combination of shorts and shoes, so here’s a guide on what shoes you should wear with shorts.

The Shoes You Can Wear With Shorts

There’s a few different kinds of footwear combinations which work with shorts. Knowing the types of shoes you can wear is important. As already outlined, even smart shorts are at the smart-casual end of the clothing formality scale, so you should leave out the most formal of footwear.

You should match up your footwear choice with the choice of shorts you wear. This is usually dictated by the occasion. More formal options like loafers will work well with chino shorts. A pair of sliders will go well together with swim shorts.

The shoes which look the best with shorts, from most formal to most casual, are:

  • Loafers
  • Boat Shoes
  • Espadrilles
  • Smart Casual Trainers
  • Sports Trainers
  • Sandals/Sliders

You should also remember that the overall look you’re going for is wearing shoes without socks. However you will be wearing shorts with socks, which are called no-show socks. These shoes are the ones which look best when it appears you’re not wearing socks.

If you try for anything more formal, such as Oxfords, they will not go well together with even the most formal of shorts such as tailored, and will not look good with a sockless look.

There’s also different fastening options; From lace ups to slip ons.

It’s also worth mentioning the material of your shoes too. A lot of the shoes come in different material, which can denote formality, e.g. a pair of canvas trainers is more casual than a smart leather pair of trainers.

Materials to look out for are: Hard leather, suede, canvas or a mix which you’re likely to find in trainers.

Matching Your Shoes To Your Shorts

As with everything else in men’s fashion, you should be matching the right pair of shoes to your shorts. First of all, this depends on what shorts you’re wearing.

As with other clothing, they can range from smart to very casual, but generally speaking, shorts are seen as a more casual option than other types of clothing for your lower half.

With that said, if you’re wearing a pair of smart shorts, you’ll want to pair them up with some smarter footwear. At the other end of the scale, if you’re wearing casual shorts, you’ll want to combine them with more casual footwear.

What Shoes To Wear With Tailored Shorts

I’ll start off with the most formal, tailored shorts. They’re the smartest shorts, and therefore the smartest footwear should accompany them. A pair of loafers, leather or suede will work here, and will keep you looking smart.

Other slip ons such as some smart espadrilles could also work, and if you’re looking for lace ups, perhaps the only ones which will work well will be boat shoes.

What Shoes To Wear With Chino Shorts

Next down the list of formality will be chino shorts. They are by far the most versatile, and you can wear them around town, to a BBQ or garden party, or almost any other occasion.

With that said, you can keep things smart by wearing a pair of loafers, casual things down by wearing sandals or sliders, or meet somewhere in the middle, with a pair of smart casual trainers or espadrilles.

When it comes to shorts, chino shorts are the ones to pick out if you’re unsure about everything else.

What Shoes To Wear With Denim Shorts

Denim shorts are more informal, and come under the more casual side of a smart casual look. Just like full length jeans, this can depend on the colour of denim you choose. Mid to light shades of blue are casual, with darker shades and black looking smarter.

White is a great colour for summer, and can be paired with so many things.

If you’re going for the more casual types of denim jeans, match up the footwear. A pair of casual trainers will be fine, as will a pair of minimalist trainers such as Stan Smiths. With the smarter denim being black or white, you may be able to wear some of the smarter footwear mentioned, such as loafers.

What Shoes To Wear With Sweat Shorts

One of the most casual styles of shorts, sweat shorts are the laid back, relaxed style of shorts you can wear.

What footwear should you wear with sweat shorts?

A good go to pair would be sports trainers. A pair of Air Max or Converse will not look out of place. Whether you’re lounging around or doing a sporty activity, you’ll look the part with this combination.

What Shoes to Wear With Swim Shorts

If you’re off on holiday and are wondering about beach style or what to wear around the pool, swim shorts are the style you’ll be looking to go for.

But what footwear is best suited to swim shorts?

The options here should be Espadrilles if you want something more substantial, but most likely, sliders, flip flops or sandals. Most swim shorts can be worn around town as a universal style of garment, but they’re best suited in their natural environment.

Going for a pair of sandals or sliders will keep the overall look laid back and casual, and pairing them with a nice pair of swim shorts will keep you looking stylish on your holiday, home or abroad.

Just make sure you remember: Don’t wear socks with sandals or sliders!


And that’s your guide on what shoes to wear with shorts. The takeaways from the guide are to pair the right shoes with the right shorts, and wear them in the right setting, at the right occasion. Now you know what shoes to pair with what shorts, you can dress with confidence.

Have fun with your summer fashion this year pairing the right shoes with the right pair of shorts.

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Michael Adams

About Michael

Michael Adams is the founder and editor of Michael 84, blogger and T-shirt designer from Newcastle, UK. Sharing men's fashion tips, style advice and lifestyle information for all guys.

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