The Best Shoes To Wear With Shorts

The Best Shoes To Wear With Shorts

Summer is here! 

You’ll undoubtedly have a few pairs of shorts that are ready to be worn, so let’s look at the best shoes to wear with shorts.

Knowing what kind of shoes to wear with shorts is crucial to creating a fashionable look. We have created a guide to help you navigate the best smart and casual shoes for shorts, so you can rest assured knowing you won’t risk a fashion faux pas this summer!

Whether it’s a summer stroll, lunch in the beer garden or a mild evening walk, we’ll help you find shoes that look good with shorts. So, no matter your preferences, you’ll achieve style success with a pair of Cheaney’s shoes.

Finding shoes that look good with shorts 

Shorts are the ultimate summer casual clothing, which can be dressed up or down depending on their style. Before we delve into what shoes to wear with shorts, here are our top three tips on how to find what style will work best based on your outfit choice:

  • Consider the occasion: The type of shoes you choose should depend on the occasion and dress code. For example, trainers are appropriate for casual events, while loafers are suitable for more formal settings.
  • Stick to neutral colours: Neutral colours such as brown and black are versatile and can be paired with various shorts.
  • Match the style: The shoes you choose should complement the style of your shorts. For example, boat shoes or loafers look great with chino or linen shorts, while trainers are perfect for denim shorts.

Casual shoes to wear with shorts

Just because your legs are out, it doesn’t mean you can forget about what’s on your feet! Whether you’re trying to achieve a classic and trendy look or something more athletic, plenty of casual shoe styles can be paired with shorts.

Shorts and trainers

If you’re wondering what trainers to wear with shorts, look no further!

Certainly the most popular shoe choice to wear with shorts, trainers are something everyone owns and are traditionally the go-to style to pair with shorts.

Any clothing you enjoy wearing that gets a lot of use is worth investing in, so upgrading your current pair of trainers to something of quality is a worthwhile decision for many reasons.

Cheaney X Goral Trainers

A trainer made using natural materials like suede or leather offers a much more comfortable experience, especially in the summer months, as they will take the shape of your foot, and the pore structure allows moisture to dissipate from the shoe and keep you cool – both in look and temperature. Compared to cheaper man-made composites found in many other options, the natural materials will also last much longer and look better with age. 

Cheaney X Goral Kelham Black Chromexcel Trainer

In terms of versatility, the same rule applies to trainers and dress shoes – keep it simple. Dark leathers add a smarter edge when worn with shorts, whereas suede (or a mix of the two) would be a more relaxed option and add a subtle depth of interest. 

Cheaney X Goral Hallam White Leather/Rock Suede

Smart shoes to wear with shorts

Not all shorts are designed to be worn at the beach! If you want to keep a smart and crisp appearance whilst strutting the streets, smart shorts will keep your legs cool this summer. You’ll likely want to opt for a smarter shoe when wearing more formal bottoms.

Loafers and shorts

For a step up in formality, loafers bridge the gap that has been confusing people for decades: that of smart and casual.

This historic design started as a house slipper, so it makes sense that it still has a laid-back feel and can work excellently with shorts. Its laceless design means they couldn’t be simpler to put on or take off, perfect for impromptu paddles in the sea or catching the rays. 

Hunt Men’s Driving Shoes

Unlined suede loafers are particularly suited to be paired with shorts due to their lightweight, flexible construction. The vibrant colours available allow adding some flair to your ensemble and work well with lighter-coloured clothing.

Toby Unlined Flexy Loafer in Rustique Janus Suede

As with trainers, a leather loafer is a more formal option, generally sitting well with darker tones like grey and navy. Pairing these with a shirt and an unstructured blazer on the top half creates a well-considered look for those warm evenings, proving that you shouldn’t have to compromise on style when the temperature rises.

Harry Tassel Loafer in Black Calf Leather

Derby shoes and shorts

To dress your shorts up further, you could pair them with derby shoes – they represent a casual take on a dress shoe and would be a more formal pairing with such outfits. 

A nice pair of suede derbies adds a softness which ties in with this look very well, though you should not shy away from leather derbies, provided that the shorts are a tailored fit and are well-pressed.

When wearing any shoe style with shorts, the popular choice is to wear a sockless look. However, from a practical perspective, using no-show socks with leather-lined shoes like these would be advisable as you’ll find them much more comfortable.

Dalby in Eco Hunting Green Suede paired with an invisible sock


With warm-weather clothing, the items that go into the ensemble are fewer than in winter, as you’d be mad to try and layer up when the temperature is high. With this in mind, your chosen accessories will likely make a bigger impact. 

To dress up the summer outfit properly, a good quality belt that corresponds with your shoes makes a big difference in making your style look complete and well thought-out.

Dark Leaf Leather Belt with a matching a pair of Dark Leaf Harry Tassel Loafer

Buy shoes for men to wear with shorts online at Cheaney

However you’d like to style your shorts, we’ve got you covered – apart from your knees. Shop our full range of men’s footwear to upgrade your summer shoe collection, meaning your old trainers can be kept for the gym instead!