Summer is here, and so is shorts season. While ladies have a veritable treasure trove of outfit choices to pick from, men usually have to fall back on shorts, a summer style staple. While shorts are an obvious choice, the type of footwear you pair with them can be a trickier decision. It can be tempting to fall back on flip flops, but why settle for a pair of shoes that are less than suited to the elements? Find out what shoes to wear with shorts with our top suggestions for the perfect shorts and shoes combo.

Boat shoes

They are a staple of men’s footwear that will never go out of style. They’re incredibly versatile, looking great paired with jeans and a sweater or shorts and a casual t-shirt. Boat shoes are dressier than trainers or flip-flops, and yet don’t compromise on comfort. It’s hard to find a pair of shorts that boat shoes won’t match: they’re a great shoe for day to night transition, and an essential on a walking holiday. A classic blue or brown pair, such as Robinson’s Loake 582, are a real investment that will see you through summer and the transition into autumn.


If you’re thinking about what shoes to wear with shorts for a more formal occasion, these work well with tailored style shorts; they definitely offer a smarter look, perfect for those long, warm summer evenings. A pair of loafers are a great way to make shorts accessible for evening wear – although they are best paired with tailored or chino shorts, to ensure their more formal style works with the rest of the outfit.


Boots, you say? Surely not. Well, brush the dust off the boots at the back of your wardrobe; boots are surprisingly versatile, and can work very well with shorts if enough thought is put into the outfit. Desert boots, like the Anatomic Gel Colorado can work very well with shorts, especially chino shorts. Pair this with a jumper for a relaxed, easy-going look that leaves your flip-flops far behind.

Canvas shoes

Shoes made from canvas are a great choice for an active day: they are comfortable, breathable, and easily matched with most types of shorts. Longer denim shorts work particularly well with canvas shoes, giving a casual, nonchalant summer look. While canvas shoes may not hold up well in terms of durability, they certainly are comfortable, and are probably one of the most accessible choices for a man unsure about his styling choices.

Whatever shoes you wear this summer, make sure they reflect you and your personality. It’s easy to throw on a pair of flip flops, but with our huge range of shoes to offer more exciting combinations, why not challenge yourself to a style overhaul this summer?