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Get Your Legs Out and Wear Shorts with Style: The Best Mens Shorts

In the nineteenth and early twentieth century, shorts were just an item designated for young boys, they were only worn until puberty, upon which the boys were given a pair of trousers.

It was an unofficial ceremony of entering manhood in a way. But we as fashion-forward modern gentlemen know that this isn’t the case anymore, in fact shorts are a staple of summer wears and get nearly as much attention from designers as regular trousers do.

The evolution from boyish garment to fashionable summer piece has taken some decades, being slowly brought in through the professionalization of sports like tennis, soccer and rugby. Men who were more adventurous and had the confidence nurtured from their sport started wearing shorts off the courts and pitch, which influenced every young lad who wanted to grow to be the next best sportsman.

Shorts have come a long way, since the ancient days, shorts were worn on centre court at Wimbledon. They now grace the catwalks at fashion week, the beaches of tourist hotspots and can be seen anywhere where there is some nice weather. Yet there are still some questions to be answered; when does one wear them? When should one stay clear of shorts? How do you pick a good pair of shorts? What length, fit, material? Don’t worry, we shall cover everything clearly.

best mens shorts

"The evolution from boyish garment to fashionable summer piece..."

The two obvious times to wear shorts are; when playing sport or keeping fit or even more obviously; when it is warm. Apart from that the times to wear shorts are few and far between. Effectively, the season for wearing shorts will fall under these two categories.

With regards to occasions to stay clear of wearing shorts, there are quite a few, which I will bundle. You should never wear shorts to a formal occasion; dinner parties, weddings, proms, funerals etc. a rule of thumb: if you could wear a tie or a blazer to the event, don’t wear shorts.

Secondly, there are occasions where you can wear shorts if it weren’t for who you are with.

If you wear shorts on a first date, you’re doing it wrong (unless you’re going to a water park, that’d be awesome). You shouldn’t wear shorts to an event where you are unfamiliar with the people, as in if they’re not a family, even if it’s during the summer, opt for some smart linen trousers.

Finally, anytime you want to be taken seriously, for example; if you get invited to your works summer party, but you want to appear serious and still relatively corporate, don’t wear shorts. Apart from these scenarios, go nuts, enjoy the freedom which shorts bring.

Now onto the serious questions; how to pick a good pair of shorts. The biggest things to consider when picking a good pair of shorts are style, fit, and length.

What to Consider when Purchasing a Short

There are myriad styles of shorts, but they all seem to follow pretty similar patterns, so I will endeavour to outline the most common styles and what they are best suited for and how to choose the best for you.

  • ​Firstly, let’s consider running shorts, often much shorter in length than any of its brethren, and made of a loose fitting, flexible material allowing for maximum mobility.

While most running shorts provide the same loose fit and floaty material, something to look out for is sweat wicking materials which reduce the chances of getting friction burns, which can be common among long distance runners.

Something else to consider when buying running shorts is price; don’t get swindled by some companies claiming they’ve got the latest running technology, they haven’t and they aren’t worth $150.

  • Next, the smart shorts. Smart shorts seem to work against the general theme of shorts, which is to be free and relaxed, yet somehow they have grown in numbers and styles over the last few years. Buying smart shorts is a little more difficult than buying other pairs, given that it is completely up to the occasion whether they’ll be a hit or a miss.

If you’re going to a garden party or pool party, perhaps go for the crisp white linen shorts, which should be well fitted but loose enough to give you freedom.

Here are some tips to help reduce the headache:

  • stick to singular neutral colours​
  • have them fit more snuggly than regular shorts
  • opt for a higher quality material
  • eep the length just above the knee and pair with a belt

The last pair we’ll consider are casual shorts; this can be anything from your generic board shorts to chino shorts. The rule of thumb with casual shorts is to be comfortable, not too loose (think NBA shorts) and make sure they don’t slouch at the back (this makes them look ridiculous, like gangsters with their shorts around their ankles).

Here are some general rules for shorts to consider when looking through the list below.

  • The length of a pair of shorts should be 2-3 inches above your knee when standing perfectly upright, and just covering when sitting down.
  • Don’t go too high, you’ll show too much leg and it will look a bit revealing, too low and they are no longer shorts.

The fit of the short depends on the style; when in doubt have slight taper from the hip to the end of the short, this will help with making you appear more V-shaped and athletic. Now let’s get to:

The Best Mens Shorts on the Market

Athletic Shorts

Nike 7” Distance Running Printed Dri-Fit Shorts ($55)

Nike 7” Distance Running Printed Dri-Fit Shorts

These are the sweat wicking shorts I was talking about earlier, they help move the sweat off the shorts and the body meaning you don’t get itchy.

The shorts are built with a proprietary polyester construction which works to stretch in two ways meaning the shorts move with your body, keeping with your every step and movement.

If you’re serious about getting in some road time, keeping fit or getting in cardio generally, these shorts will serve you well. If I was to try and sell you on these shorts, I would say, they’re Nike, they’re reasonably priced and they do what it says on the tin.

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2XU Ice Compression Shorts ($90)

2XU Ice Compression Shorts

If you aren’t familiar with compression shorts, let me give you a little run down of its features. Compression gear works to increase blood flow to your muscle covered in the compressive garment; this reduces soreness, and speeds up the removal of lactic acid and other by-products of physical exertion.

Effectively, it leaves you less sore the next day and works to reduce recovery time while improving performance.

When this trend picked up in 2001, 2XU popped up and started producing high quality compression gear. The shorts featured have antibacterial properties and have UPF 50+, on top of its main function. If you’re looking to up your game, then getting these shorts will get you a step closer to your goals.

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Nike Men's Tech Fleece Shorts ($84)

Nike Mene Tech Fleece Shorts

Nike just had to make another appearance. These shorts are the perfect combination of comfort and functionality. They are made out of a cotton-polyester blend to maximise softness and stretch to match your needs.

​These shorts are ideal for the gym and can easily be worn post-workout for a more casual look. Combine the shorts with an easy breathing top to get the most out of your workout.

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Boast Court Shorts ($65)

Boast Court Shorts

A brand which dates back to 1973 uses its heritage to draw on 70s retro for their sportswear classics.

These shorts, reminiscent of 70s racket sports, are ideal for tennis, squash, and badminton players. The deep front pockets are perfect for keeping extra balls or shuttlecocks in.

A lightweight and breathable material will keep you cool as a cucumber in those heated matches where you need to stretch to tip it over the net.

Pair the shorts with a standard white polo or a breathable white Adidas tee to finish off the retro vibe.

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Adidas Football Shorts (soccer) ($50)

Adidas Football Shorts

One of the few times you can get away with wearing short shorts is on the soccer field.

The reduced amount of cloth aids the movement and flexibility of the athlete, meaning they can strike the ball more freely and by extension more accurately.

These Adidas shorts are another throwback to 70s and 80s within English soccer, where mop-headed players ran around in long-sleeved heavy cotton or wool tops yet chose to wear shorts akin to underwear.

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Smart Shorts

Etro Slim Fit Striped Cotton Shorts ($430)

Etro Slim Fit Striped Cotton Shorts

One can clearly see a nautical influence when looking at these exquisite shorts, crafted in Italy; the pair scream class and something fit for a boat-party (if you are lucky enough to be invited to such a shindig).

The sky blue and snow white stripes are accentuated by the yellow of the hems. The colours work together to mimic the hues of a summer’s day, encouraging a floated feeling of relaxation.

To finish off the outfit, combine the shorts with a Ralph Lauren polo or a very simple plain white shirt. Too much going on with the top would make the whole thing look like overkill.​

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Hartford Linen Shorts ($175)

Hartford Linen Shorts

I’m afraid that a good deal of the smart shorts in the list will follow the theme of the foppish middle class, touting bright reds and brilliant whites seems the standard among the preppy millennials who govern the space.

While association with such a theme is not ideal for a modern gent looking to combine multiple styles and not just look like a page out of Ralph Lauren's most recent catalogue, these shorts are a pair worth considering.

The red linen works wonderfully well on a hot summer's day, with the material being ever so light and comfortable. Combine these linen shorts with a pair of dark brown suede boat shoes, which will add to the preppy look, but will certainly make you stand out.

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Freemans Sporting Club Cotton Twill Shorts ($160)

Freemans Sporting Club Cotton Twill Shorts

I did warn you about the continuation of the preppy style and bright colours, so here is another pair. These salmon coloured shorts may not be for everyone, but those of you brave enough to chuck on a pair of pink shorts will certainly be noticed at the garden party, and if you pull it off correctly you’ll look pretty darn dapper.

The soft-cotton twill allows you to be comfortable in the hot blazes of a Californian summer or the lighter warmth of a Spring Sunday at the park with the family. All in all, these shorts are a great addition to your garment collection, they are a versatile warm-weather essential and should not be glossed over because of the colour.

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Incotex Linen and Cotton-Blend Shorts ($275)

Incotex Linen and Cotton-Blend Shorts

These shorts are beach party and work party aprope, they seamlessly blend understated style and relaxed fashion into one stalwart of the sophisticated gents wardrobe.

The linen-cotton blend ensures a softer short and makes them even more comfortable than regular linen. The belt loops on the shorts encourages two things; one, to wear belt (duh) and two, to tuck your shirt in once belted up.

To turn these shorts into a winner outfit, take a matched woven leather brown belt with the same leather tassel loafers, and add a coloured shirt to finish it off.​

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Vineyard Vines- Embroidered Whale Chino Shorts ($107)

Vineyard Vines- Embroidered Whale Chino Shorts

These are perhaps my favourite on the list, they’re smart, expressive, fashionable, and quite honestly they’re just fun. These shorts are 100% cotton, meaning they have a nice structure to them.

Perfect for a belt and a short sleeved shirt, these shorts will suit you well going anywhere you want to look smart but want to show a bit of humour.

Oh and those little whales you see on the shorts are emblazoned with the American flag. That’s awesome.

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Casual Shorts

All Saints- Mitre Lumen Shorts ($110)

All Saints- Mitre Lumen Shorts

All Saints are a fantastically weird and wonderful London brand who epitomise industrial chic.

The company, which often have Victorian industrial ironware to house the clothes in their shops, produce a wide range of toned-down colours with dark hues and a slightly slimmer fit.

These shorts epitomise an All Saints summer line, with this sandy colour being the brightest they will probably go. However, if you like the modest, slightly grungier version of a summer short, these guys are for you.

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Alexander McQueen Printed Cotton Shorts ($615)

Alexander McQueen Printed Cotton Shorts

A little bit pricey but an all-together quality pair of shorts. Alexander McQueen is obviously known for its luxury and kooky designs, and as you can see here they have stuck to what they know.

The shorts, which were made in Italy, are partially lined and have a standard hook and zip fasten.

Wearing these will certainly grab some attention; some good, some bad, either way you’ll be noticed. The pricey pair isn’t made out of anything special, but they are a wonder to look at; like a piece of sartorial art.

If you love crazy designs and don’t mind getting a few looks, then these shorts are ideal for you.

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Todd Snyder + Champion Cargo Shorts ($120)

Todd Snyder Champion Cargo Shorts

Subtle and soft, these shorts are made of 100% cotton for your comfort and fit in a way where they retain their structure yet are loose enough to relax in.

To aid the comfort, they are fitted with an elasticated drawstring at the waist, so you can decide exactly how tight or loose it is around your gut.

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Bonobos Nomad Shorts ($68)

Bonobos Nomad Shorts

One of the cheaper options on the list, these shorts are perfect for hitting the beach, laying around at home or basically just having a chilled time.

The crazy blue floral pattern may not be for all of you, but for those of you who like surfer/island-life look these couldn’t be much better.

If you’re brave and adventurous you can even have them with a crisp white cotton shirt and make them beach bar worthy.

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Sasquatchfabrix- Sashiko Cotton Shorts ($370)

Sasquatchfabrix- Sashiko Cotton Shorts

Yes, that is one word, it’s not a typo. The brilliantly named Sasquatchfabrix, a Japanese cult label, have produced a fine piece of garmentry with these shorts.

The shorts are patterned with little white crosses on a navy background and are constructed of 100% cotton. The method of making the pair is in the name; sashiko.

Sashiko is a type of stitching, which translates to little stabs, ominous I know, but it’s the way the needle goes through the fabric.

If you are willing to pay out the $370 for a piece of the label who have been at the helm of a cult following for the last decade, then these shorts are good fit for you

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CONCLUSION

Hopefully over the course of this list you have learned what sort of shorts you want, how to choose them and how much you're willing to spend. Remember that shorts are seasonal so they should last a long time, but also as fashion changes, a $300 purchase one year might be out of style by the next.

What do you think?

Written by Terrence Kennedy

Terrence Kennedy is the man’s man on a journey to self-discovery. A traveler, extreme sports aficionado, an observant wanderer, a DIY-Know-How, an ultimate outsider and a documentarist of culture, sex, dating, relationship, fashion, style and gentleman's etiquette. He has learned a lot through his escapades, and is happy to pass that knowledge on to you.