They say you can tell everything about a man by his shoes, which is why you should pay close attention when picking your warm-weather footwear – especially if you’re wearing shorts, when your footwear choice is front and centre.
With this in mind, we’re set to highlight some foolproof shorts and footwear combinations for summer, so you can avoid any unsightly clashes.
Especially versatile, tailored shorts can be dressed up or down to suit the occasion and make the ideal warm-weather alternative to formal trousers for smart-casual events such as garden parties and wedding receptions.
The rule to remember here is that smart shorts should be paired with an equally smart shoe, so team tailored shorts with your finer footwear silhouettes. Brogues, Oxfords and Derbies will all work well, whether you opt for models in leather or seasonally-appropriate suede, while chic loafers and driving shoes in similar luxurious materials will add a more laid-back feel, but still keep you looking unmistakably refined.
Of course, these styles will only look sharp provided they’re worn sock-free. So, if you’re not up to scratch on going sockless, then best brief yourself properly before getting your hairy pins out. Suffice to say, you’re going to need to invest in some invisible shoe liners.
When the mercury really spikes, classic leather sandals (nothing too fashionably sporty) in timeless navy, black or brown will help maintain a refined appearance; while scruffy canvas trainers, flip-flops or other decidedly casual styles will only jar with the sharp, tailored cut of your legwear.
With sports luxe and streetwear influences dominating industry trends over the past few years, jersey, nylon and other sports-inspired shorts have become de rigueur for contemporary men that like to dress down, rather than up.
If you’re more likely to be seen in a pair of athletic shorts than sharply tailored versions, you’ll want a shoe that offers the same degree of comfort and breathability.
What better than a pair of trainers? From luxury designer takes and technical runners to slip-on canvas plimsolls and even hi-tops, it goes without saying that the humble sneaker is an ideal match for jersey shorts.
That said, a pair of low-top minimal trainers in black, white or grey is probably the style to settle on if you’re prioritising versatility. Not only will they lend a sleek edge to your shorts, they’ll also act as a handy tool to dress down your suit when you want to put a casual spin on your tailoring.
Fans of the streetwear aesthetic should also consider pool sliders, especially once temperatures rise. A current footwear trend, the more progressive dressers in our midst can team theirs with white sports socks – a two-finger salute to conservative tastemakers. Adidas makes some of the best on the market and they’re guaranteed to get good use for many more summers to come.
You’d be hard pushed to find a man that doesn’t already own a pair of denim shorts. Great for holidaying and weekends in the city, they are a fail-safe short choice for last minute outings and days when you don’t want to think too hard about what to wear.
But although it’s easy to style a pair of selvedge shorts with most of your casual shirts, tees and vests – after all, they are the summer equivalent of your trusty jeans – what are the guidelines when it comes to footwear?
Keep it lo-fi. While designers and stylists might be re-imagining denim lately, even working it into eveningwear options, the fact remains that denim cut-offs are unquestionably casual. And unlike sporty styles, they have a little more of a grunge-inspired kick to them, so footwear that’s fuss-free and fashionably offbeat is the way to go.
Try teaming with canvas trainers (rock-affiliated Chuck Taylors being the obvious option here), minimal plimsolls or skate-inspired slip-ons (Vans are the go-to for this style) for effortlessly cool off-duty looks, switching for a pair of espadrilles if you’re planning on taking your denim to the sand dunes.
Unbeatably versatile, a pair of chino shorts is an indisputable summer wardrobe staple. Straddling the line between smart and casual, you’ll quickly come to realise that there are few footwear styles that don’t play well with chino shorts.
For a classic pairing that works for almost any warm-weather situation, team them with boat shoes. Although a casual silhouette, there’s something unmistakably sharp and gentlemanly about a boat shoe that means you can easily sport them for slightly more formal events.
Another silhouette that might not immediately spring to mind is the desert boot – something too many of us mislabel as ‘autumn/winter only’. Boots can work with shorts (we recently debunked that outdated myth once and for all), especially if you opt for suede versions in lighter colourways, which will add a rugged yet polished feel to your ensemble.
Still, if you really want to smarten these up, stick to suede or leather brogues, Derbies, drivers and loafers, which will highlight your shorts’ tailored look rather than the relaxed chino fabric itself.
Alternatively, if you’re hitting the beach or hanging by the pool, espadrilles and sandals will work just as well to keep your summer style on-point. There really is nothing this type of short won’t go with.
If you’re a shorter gentleman, opt for low profile footwear silhouettes (nothing above ankle height) with a good sole or slight heel in shades that are similar to your skin tone – all of which will combine to produce the illusion of height and longer legs.
When it comes to your shorts, go for a pair that finishes around mid-thigh or give the hems a couple of folds to emphasise leg length.
Image: Eidos Napoli SS15
On the opposite end of the spectrum, if you have long legs, you’re going to want to opt for footwear styles that have a slightly higher profile. Desert and chukka boots, along with slightly chunkier trainers, brogues and Derbies, would be ideal.
Similarly, your shorts should finish on or just above the knee, in order to break up your vertical lines slightly lower down and reduce the amount of leg on show.
Image: J.Crew SS14
Leather Boots & Shorts
For an altogether edgier take on summer dressing, try combining a pair of leather worker boots with your shorts. The key to pulling off this dramatic juxtaposition is to ensure that your shorts are equally rugged – think heavyweight twill or denim styles in straighter cuts.
Image: AllSaints SS13
If you intend to bare your feet in a sandal or flip-flop this summer, spend some time making them look presentable beforehand. That means getting a professional pedicure (there’s no shame in it anymore), or doing a bit of DIY grooming in the comfort of your own home.
At the very least, your toenails should be neat and clean, there should be no unsightly hard patches of skin along the sides or top of your feet, and you may even want to consider trimming any excess hair.
Whether you’re packing for a summer holiday or just figuring out simple rules to refine your style this season, sticking to our fail-safe shoe pairings will keep your feet looking sweet as we sail through summer.
What are your personal tips for shorts and footwear styling?
Let us know in the comments section.