The Best Shoes to Wear With Shorts

Written by Dan | 27/06/2022



Ultimate Guide

Ah, the age-old question: what are the best shoes to wear with shorts? It can be a tricky decision, but never fear – we’re here to help.

In this guide, we’ll show you how to choose the perfect summer footwear for your shorts style. So whether you’re going for a classic look or something more trendy, we’ve got you covered. Read on for our top tips!

A guy in denim shorts leaning

The Classic Look – chino shorts & boat shoes

Just because you’ve got your legs out doesn’t mean you have to sacrifice style. For a classic look, team chino shorts with some loafers or boat shoes. If it’s a smart-casual occasion, you can even go for a pair of brogues.

Just make sure your best shoes are well-polished – no scuffed shoes allowed! Choose fashionable shoes – wearing shorts doesn’t automatically equal scruffy, so don’t let your footwear choice reflect that.

For a more relaxed take on the classic look, try teaming denim shorts and a tailored shirt with a pair of Converse or Vans. This is perfect for weekends spent BBQ-ing or at the beach. Just make sure your shoes are clean – there’s nothing worse than dirty trainers!


The Trendy Look – denim shorts & loafers

If you’re looking to add a touch of trendiness to your outfit, start with casual shoes. Wear loafers without socks to add interest to an otherwise simple look. They also work well with both chino and denim shorts.

Another pair of shoes that are perfect for summer are espadrilles. They’ll instantly elevate your look, but they’re still casual enough to be worn with denim or cargo shorts. Just be careful not to go too overboard with men’s fashion trends – one statement piece is enough.

If you’re feeling a bit more adventurous, why not try a pair of minimalist sneakers with your shorts and T shirt? This look is perfect for weekends or casual days at work.

Just make sure your shorts are on the shorter side to avoid looking too casual. And if you’re really wanting to make a statement, go for bold coloured canvas trainers – think red, yellow, or even green!


The Dressy Look – tailored shorts & sandals

For a dressier occasion, team your shorts with some nice leather sandals. If it’s summertime and you want to show off your tan, go for a pair of open-toe sandals like Birkenstocks.

There are plenty of styles of sandals for men, so you’re sure to find a pair that suits you. Just make sure they’re not too flashy – remember, you want your shorts to be the star of the show.

Trying out different shoes with your shorts is a great way to experiment with new styles. And who knows – you might just find your new favourite summer look! Just make sure your footwear isn’t too chunky (lose the desert boots!) – the goal is to look effortless, not clunky!

Khaki shorts are a great option when you’re putting together a slightly more dressy outfit. The perfect pairing for a fitted polo shirt and canvas sneakers, this look is perfect for a summer evening out and smart enough to carry off dress shoes.


The Beach Look – swim shorts & flip flops

If you’re heading to the beach or just want a more relaxed look, team your tailored swim shorts with some flip flops or sliders. This is the perfect opportunity to break out those fun patterned or colourful pairs that you wouldn’t normally wear! Just make sure your feet are in good shape. Nobody wants to see funky nails or dry, cracked heels.

Flip flops are a great option for the beach because they’re easy to slip on and off. But if you’re doing any amount of walking, they might not be the most comfortable option. In that case, try out some sliders instead. They’ll stay on your feet better and provide more support.

There are so many casual outfits for men in the summer. And with the right shoes, you can take your look from drab to fab! We wrote a post about the best men’s summer shoes – don’t say we never get you anything! Just remember to keep it effortless and relaxed – after all, it is summertime!

Kicking back in shorts and trainers


The Gym Look – athletic shorts & trainers

If you’re hitting the gym or going for a run, it’s important to choose the right shoes. You want something that’s lightweight and breathable, with plenty of support.

Running shoes are a great option, but if you don’t like the way they look with your shorts then try out some training shoes instead. They’ll give you the same level of support without being too bulky.

And if you want to show off your new shoes, try out a pair of running shorts! They’re usually shorter than regular shorts, so they’ll show off your kicks nicely.


The Barefoot Look

Of course, there’s no rule which says you have to wear shoes with your shorts! If it’s a hot day and you’re just lounging around the house, why not go barefoot? This is the perfect opportunity to show off that pedicure! Just make sure your feet are clean and presentable before you start walking around.

A barefoot man walks along a pool in shorts

Photo by Marvin Meyer on Unsplash

To wear socks or… not?

The eternal question – should you wear socks with shorts? The answer is, it depends. If you’re wearing a pair of sandals or flip-flops, then definitely not. But if you’re wearing sneakers or loafers, it’s up to you.

If it’s hot out and your feet are likely to get sweaty, then go sans socks. If you’re just going for a casual look, it’s perfectly acceptable to wear socks. Just make sure they’re not too chunky or colourful – you don’t want them to steal the show from your shoes!

You don’t have to cover your bare legs with long socks, however. There is always the option of invisible shoe liners or trainer socks. A good pair of no-show socks are almost unnoticeable and makes the perfect compromise.


In conclusion

The best shoe styles to wear with shorts are those that suit your style. Whether you’re going for a classic, trendy, or dressy look, there’s a pair of shoes out there that will finish off your outfit in style. If you’re looking for a universal shoe to carry you through the warm weather, then a crisp pair of white sneakers is your best friend.

If you haven’t decided which type of shorts to go for, take a look through our ultimate shorts guide. No matter what your style is, there’s a shoe out there that will go perfectly with your shorts. Whether you’re wearing boat shoes or leather sandals, you can wear shorts with confidence.

And when the warm glow has faded, and the nights start drawing in, don’t panic. We’ve put together a comprehensive guide to the best trainers for winter. We’re just that prepared!


Shop your spring and summer outfits with Mainline Menswear

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