The Best Shoes To Wear With Shorts

The Best Shoes To Wear With Shorts

Summer is coming.

It surely won’t be long now until your heavy coats, scarves and hats will be squirrelled away until next year, and the summer wardrobe is reintroduced. No doubt you’ll have a few pairs of shorts in there, so let’s have a look at ways that you can still wear good shoes with what is the ultimate in summer casual clothing.

Even shorts have the capability of being dressed up a little, depending on the style; opt for a nice cotton for comfort and breathability, cut above the knee and nicely ironed. As with any outfit, your choice of shoes can work in tandem to complete the look, whether it’s a summer stroll, lunch in the beer garden, or a mild evening walk.


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

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

Cheaney X Goral Collaboration The Steel Trainer

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 on many of the other options out there, the natural materials will also last a lot longer and look better with age. 

Cheaney X Walsh Bannister Trainer in Fox Suede (left) and Blue Palio (right)

In terms of versatility, the same rule applies for 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 adds a subtle depth of interest. 

Cheaney X Goral Mellor Trainer in Dark Brown Chromexcel (left) in Black Chromexcel (right)


Pretty much the definitive summer shoe, sandals are undergoing a bit of a renaissance due to their nostalgic appeal and practicality. Catered towards the summer months, a good pair of sandals offers unparalleled breathability and is much more appropriate for warm weather strolling than dreaded flip-flops.

Bertie Goodyear Welted Sandal

Again, quality of materials should be the main focus here. The design speaks for itself, so get yourself a classic welted pair for comfort, support and longevity.


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 life as a house slipper, so it makes sense that it still possesses 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. 

Unlined suede loafers are particularly suited to being paired with shorts due to their lightweight, flexible construction. The vibrant colours available offer the opportunity to add 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 will be a slightly more formal option, generally sitting well with darker tones like grey and navy. Pairing these with a shirt and 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

To dress your shorts up further, you could look at pairing them with a pair of derby shoes – they represent a casual take on a dress shoe, and in turn would be a more formal pairing with outfits like this. A nice pair of suede derbies adds a softness which ties in with this look very well, though you should by no means shy away from leather derbies, provided that the shorts are a tailored fit and are well-pressed.

When wearing any style of shoe with shorts, the popular choice is to go for a sockless look. However, from a practical perspective, it would be advisable to use no-show socks with leather lined shoes like these 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 there would be in winter, as you’d be mad to try and layer up when the temperature is high. With this in mind, the accessories you choose are likely to 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

This summer, keep your old trainers for the gym and upgrade your summer footwear. However you’d like to style your shorts, we’ve got you covered – apart from your knees.