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How to Wear Shorts the Right Way

on Fri, Jul 10, 20

Shorts. They’re the summer staple that we break out the second we see a rise in temperature every single year, with a huge selection of colours, styles, cuts and fits. With so much choice, it can be difficult to know how to wear the different varieties and what pieces you can pair them with. What length is best? What style will suit you? Which fit works best? Plus, what’s the etiquette around them? Aside from the typical summer BBQ, when is it appropriate to break out the summer shorts, and more importantly, when is it not appropriate? Today we want to answer all of your shorts-related dilemmas, which is why we’ve put together our definitive guide on how to wear shorts the right way.


The History of Shorts

Shorts have had a fair bit of debate around them going back to the 19th and 20th century. Traditional English terms for shorts included “knickerbockers” and “knee pants,” and was generally considered a garment for boys rather than men, specifically when it came to school uniforms. It wasn’t until after the Second World War that adult men started wearing shorts outside of hotter climates, and this is due to soldiers being issued shorter trousers when they were stationed in tropical areas. Not only was this for extra comfort, but this was also down to cloth being rationed.

It took a while before shorts were classed as a fashion item. Post war, they were worn for sports and certain leisure activities such as tennis, and following matches, players would change into a pair of trousers before socialising. It wasn’t until the 1950s that shorts became more of a fashion garment, thanks to Hollywood trendsetters wearing them to create a comfortable, casual style for the summer. While some may still see shorts as having the school uniform connotations, there’s no denying that they have certainly earned their place in men's summer wardrobes over the years.

Shorts Etiquette

So, aside from when the weather is scorching, when is it acceptable to wear shorts? Typically, the answer is any occasion except for formal occasions and workplaces where professional attire is required. However, going into more depth, it’s of course worth mentioning that particular short styles will be better suited to some occasions more than others. As a general rule, any events that require a jacket or a blazer are not shorts-based occasions, not only because it will look out of place, but it’s a surefire way to recreate the schoolboy look.

When it comes to length, shorts that come up to your mid-thigh should be kept for exercise only. A good rule of thumb for everyday or casual wear shorts when it comes to length is to go for something that just about covers your knees when standing still.


What To Wear Them With

So, you’ve got the rules down on when to wear shorts, but what should you be wearing them with?

When it comes to shirts, there’s a range of options for you to pair with your shorts, and again this can be dependent on the occasion. As a general rule, shorts are a casual garment, so your top half should be casual too. For a simple, relaxed everyday look, you often can’t go wrong with a slim fitting tee. As your lower legs will be on show, everything above them will look thicker in comparison, so opting for tops that are cut to a slimmer fit is a must if you want to create a defined silhouette. For occasions that require something a little smarter, like a family gathering or a trip to the pub, you can pair your shorts with a collared short sleeve shirt such as a polo or button down one, which will ensure you look smart and stylish.

While during the summer months, it can be tempting to go for the Hawaiian shirt, there are far more stylish ways to capture those summer vibes. There’s nothing wrong with pairing a statement tee with your shorts, or for a smarter look you can combine with a polo shirt in a bright and bold colour. The main thing to remember? Keep the colour of your shorts toned down. If you’re going for statement prints and vibrant colours, keep the bottom half simple with lighter colours and simple designs.

When it comes to footwear, the easiest way to complete the look is by going for a simple pair of sliders. We especially love these BOSS Timeout Sliders, which are ideal for creating an effortlessly laid back look this summer. The contrasting design makes them highly versatile too, so you can easily pair them with a whole variety of short styles. A word of warning though - keep away from the socks. If you prefer to keep your feet covered, pair your shorts with a stylish pair of trainers, such as these Mallet Kingsland Trainers which will add a touch of luxury to your casual summer look.


Our Top Picks

So, now we’ve learned about what to wear with shorts and when you should and shouldn’t be wearing them, let’s take a look at some of our top picks.

Denim shorts have made a comeback recently, and they’re perfect for creating a look that’s effortlessly cool. We love these Straight Fit Denton Shorts by Tommy Hilfiger, which will pair perfectly with a pair of crisp white trainers and your favourite tee or polo. The five pocket design is practical while the Tommy Hilfiger branded patch to the back pocket finishes the look perfectly. For a smart and sophisticated look, these BOSS Casual Slim Fit Schino Shorts will fit right into your summer wardrobe. The subtle pastel colouring is perfect for summer and is great for pairing with brighter colours to create a contrasting look. They’re cut to a slim fit which will create a defined silhouette, and are finished with an understated metallic BOSS branding to the rear.

When we’re talking shorts, we of course can’t finish things without exploring some of our favourite casual styles. Sweat shorts are a must for summer lounging and lazy days, and we love these PS Paul Smith ones, which are available in a whole variety of colour ways. We especially love this vibrant red which will ensure you stand out this season. Featuring a drawstring waist and crafted in a soft and comfortable material, these fun and bright sweat shorts will pair best with a relaxed fitting tee and a pair of sliders.

For a simple way to introduce shorts into your summer wardrobe, you can’t go wrong with a classic pair of cargo shorts, and they capture 2020’s utility trend with ease. Of course when it comes to the utility trend, one brand that does it best is Marshall Artist, and these Cargo GD Shorts are a fine example. Crafted with a high quality technical fabric and featuring large pouch pockets, they’re just as practical as they are stylish. Again, paired with a simple tee and sliders, you can’t go far wrong when it comes to summer style.


Finally, a key summer staple in the world of shorts is of course the trusty swim short. Just because a tropical summer holiday may not be on the cards this year, it doesn’t mean that you can’t enjoy a bit of paddling poolside lounging, and for that, a stylish pair of swim shorts is a must. Even better, you can opt for bold colours and prints to really capture those holiday vibes. These Octopus Swim Shorts from the latest BOSS Bodywear range will certainly be a standout addition to your collection in this statement bright yellow, but you can also choose from a number of different colours too. For a more subtle way to stand out this summer, opting for vibrant prints can be the way to go, and we especially love these All Over Thunderbolt Swim Shorts by Neil Barrett, which will instantly bring some fun to your look.

We hope we’ve given you plenty of guidance when it comes to navigating the world of shorts, and perhaps even a little inspiration for your summer wardrobe. Be sure to explore our full range of shorts here at EQVVS, with a whole array of colours, cuts and fits, all from your favourite designer brands.

Written by Amy Jackson - 5th July 2020

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