Shorts Guide

The Summer Shorts Guide

Shorts simply weren’t an appropriate form of dress for the dapper chap. However, much of this has changed in the last few decades and much of the first world is aligning themselves with prep culture that has reintroduced summer shorts, not just in casual wear, but even pairing them with an appropriate button-down shirt for the office in the hot summer months. Despite its many critics like fashion designer Tom Ford who believes there is never an appropriate time for men to publicly wear shorts, the fact is that the idea of wearing shorts in the summer months has not only seeped its way into mainstream fashion, but many dandies and preps are adopting this trend outside the tennis court and off the beach.
Shorts with Sport Coats and Over the Calf Socks
Shorts with Sport Coats and Over the Calf Socks

History of Shorts

Surprisingly, or maybe not so, shorts were introduced by way of the tunic and toga that essentially paved the way for what we, today, consider the modern shorts. Initially, it was fashion-forward European men that wore what were, at the time, called ‘knee breeches’ before they were introduced into sports apparel by Americans roughly a thousand years later.
Originally developed for use by the military in the later part of the 14th century, they were used as a way to keep heavily packed and armed soldiers cooler while serving in tropical climates. The trend almost immediately caught on, and soon many civilians were beginning to sport these so-called knee trousers as casual wear.
Somewhere along the line, it was universally adopted that shorts should strictly be reserved for use by boys and not grown men. By the 1800s this was an undocumented rule strictly enforced and boys throughout Europe and North America wore shorts commonly referred to as ‘knickerbockers’ until they hit puberty at which point they would often receive their first pair of actual trousers as a gift. Since this became a staple of reaching pubescence, men began to shy away from wearing shorts to avoid appearing boyish and immature. Since then, many prep schools and urban public schools began to adopt knee pants as a standard uniform for their students, a tradition that still continues today throughout much of the world.
Boy scouts in shorts
Boy Scouts in shorts
However, as the 1900s rolled around, many companies, specifically in America, began marketing a shorter version of the knee pants as athletic wear. Shorts became a staple for both men and women while engaging in many outdoor activities and sports and so the casual formality of the knee pants fizzled as men and boys began to adopt the shorts for strict use as athletic wear.
Up until the 1930’s Tennis player wore white flannel pants until Henry “Bunny” Austin decided  to wear white shorts in a tennis match, and today people across the world wear shorts for all kinds of sports and exercises.
Despite the hard and fast sartorial rules of shorts, the routine of wearing them has flourished into the casual and even office environments of modern American and Europe. Paired with a button down shirt or even a smart polo shirt, wearing shorts has become a globally accepted form of casual dress that, at certain times, can even be appropriate for work in very specific office environments.
Vintage ad showcasing cotton twill shorts for the army
Vintage ad showcasing cotton twill shorts for the Army

Shorts Etiquette DOs & DON’Ts

Although many men would describe shorts as comfortable, they are not the number one choice for gentlemen in most situations, yet for sports on a beach vacation, or under tropical conditions, they are a god-sent. To ensure you don’t embarrass yourself by wearing shorts, make sure to keep our DO’s & DON’ts in mind.


1. Pay attention to the fit and your physique. If you have long slim legs, choose slim cut shorts that end above the knee for a great look. If you are short and a little chubby, avoid wearing shorts because it will make you look even shorter. If you have to wear them, go for short shorts that are not too tight, because you do not want to look like a pressed sausage.
When in doubt, always wear slacks rather than shorts.
2. Wear them with confidence and pride and use classic patterns use as stripes, checks or solids.
3. Consider shorts for very casual events such as backyard barbecues at friends but avoid sloppiness: Cargo shorts, a t-shirt and flip-flop will make you look like an unsophisticated college boy, while a pair of madras shorts, with polo shirt and boat shoes or loafers, will make you look debonair.
4. Wear skin-toned or heather gray underwear when wearing white or light colored shorts. Otherwise, your underwear shows through.


The standard office outfit on the Bermudas with shorts, jacket and over the calf socks
The standard office outfit on the Bermudas with shorts, jacket and over the calf socks

Types of Shorts

It seems like the styles of shorts on the market today are endless, and designers are always coming up with new ideas to present. Here’s an in-depth look at the most popular styles worn today and some style advice on how, when and when not to wear them.

Tennis Shorts

Designed for wear during tennis matches, these shorts are usually above the knee, in white with pleats allowing maximum freedom for movement. Today, synthetic materials are the way to go.
Underarmour shorts for athletes have moisture wicking fabric
Underarmour shorts for athletes have moisture wicking fabric

Running Shorts

Back in the 1970s these were short, yet somewhat loose fitting. Men like Tom Selleck were famous for these shorts, and he was often seen in them in such movies as Three Men and a Baby and his hit television show Magnum PI. Today, running shorts are generally longer, and they are made of flexible, lightweight materials that allow you to run effortlessly even without the dated look of seventies running shorts. As the name implies, these shorts are for running and maybe other sports activities but not for anything else.
Distinguish your personality with Camouflage shorts for Men
Distinguish your personality with Camouflage shorts for Men

Cargo Shorts

Very popular with casually dressed men and boys, cargo shorts are khaki shorts that have more than four pockets, often with flapped pockets on the sides of the leg.
Although practical for camping and wilderness activities where you require various tools such as a compass, pocket knife, etc. No gentleman should ever wear them outside of that setting because they simply look hideous.

Pleated Shorts

Traditionally, shorts were tailored in the same way as regular trousers and so they often had one of two pleated and depending on the fashion of the day a wider or narrower cut. Today, pleated shorts look distinctly vintage, and flat front shorts dominate the market.
Fantastic seersucker whaler shorts
Fantastic seersucker whaler shorts

Flat Front Shorts

A formal version of the casual shorts, they are often paired with a polo shirt and worn to outdoor events such as river boat tours, block parties, and informal daytime barbecues during very hot summers.

Denim Shorts

Generally baggier and longer than the short-shorts and daisy dukes worn by women, they were very popular throughout the 1970s and into the 1990s. Unless you are invited to a theme party, you should never wear these shorts.

Swimming Trunks

Bermuda shorts on the runway
Bermuda shorts on the runway

Bermuda Shorts

These knee-length shorts were of course created in Bermuda and are often worn in more formal situations such as at the office with a sport coat, over the calf socks, a tie, and even a blazer or light sweater. Since their development, they’ve become quite popular in other parts of the world as well, though generally you should not wear shorts to the office unless you are in a tropical environment where it is acceptable to wear these shorts. Outside of the Bermuda and other Tropical islands you should avoid it and go with seersucker or linen slacks instead.
Board shorts on men should only be used at the beach
Board shorts on men should only be used at the beach

Board Shorts

Originally designed as swimwear, board shorts are today worn as regular shorts as well, predominantly by young boys and very casually dressed men. They are the standard ’surf’ apparel and often feature bold prints and patterns on these below-the-knee, baggy shorts. Usually designed with a drawstring in lieu of belt loops, they are good for surfing and acceptable for beach wear but not anything else.

Chino Shorts

Simply a shortened version of the classic twill chinos or khaki pants, they were initially designed for use by the U.S. military while serving abroad in the Philippines. If you vacation in the Philippines or if you live in a similar climate chino shorts are a good option for casual wear, otherwise stick to long chinos.
Cycling shorts for men
Cycling shorts for men

Cycling Shorts

Designed to reduce chafing while riding a bicycle, these are form fitting, long spandex shorts with an insert in the area that touches the saddle. Although not necessary for casual bike rides, you definitely want them for longer tours. Apart from that, do not wear them for anything else.

Leather Shorts

Around the world, many believe that Lederhosen are a standard style of shorts in Germany, but that could not be further from the truth.
It is only worn in Munich and parts of Bavaria during the Oktoberfest in Munich. Otherwise, you will not find any self-respecting German man wear these leather shorts at any other time.
Beautiful summer madras shorts
Beautiful summer madras shorts

Plaid Shorts

Generally made of Madras, they are patterned woven shorts that have become staples in the prep community.

Shorts with Turn-Ups / Cuffs

Dressier shorts will sometimes come with turn-ups or cuffs which can be a nice little detail when wearing shorts.

What Shorts Should You Buy?

This is not an easy question and it depends on your needs but normally, a few pair of athletic shorts are important, just like swim trunks and a pair of Chino shorts. That way you are covered. If you spend a lot of time at the beach, the pool etc. you should have a little short rotation in different colors, solids, stripes and checks. Seersucker or Madras are also ideal fabrics for casual shorts.
As far as details go you can also opt for ticket pockets flaps and the same details you would find on a tailored pair of dress pants.
When buying a pair of short, you may feel like it is much less than a pair of pants, and therefore it should cost less. However in terms of labor it requires pretty much the same amount of work and most shorts are made of very inexpensive fabrics, which is why a good pair of shorts will usually cost just slightly less than a good pair of pants.

Shorts Length

For an elegant, classy look you definitely want short that end above the knee. Currently, slim fitting shorts that end 3 inches or more above the knee are popular but that doesn’t mean you have to wear them like that as well. If you have bigger thighs, it will look more flattering if the shorts are just above the knees, but it also depends on the length of your legs – you always want to look proportional. A short man with long shorts and a tall man with short shorts will look ridiculous because the proportions are off.
Personally, I have never seen anyone who looked great with shorts that extended beyond the knees, so definitely avoid long shorts.

Shorts Materials

In terms of materials, cotton is certainly a classic favorite while wool and cashmere are hardly ever used. Lately, silk, linen or blends thereof have also become quite popular. Before settling on a pair of linen shorts, you should put them on and make some sit-ups, then look at the way it wrinkles because sometimes shorts can look horrible in the front because the wrinkles are exaggerated without the added fabric weight found in regular pants. I once bought a pair of silk linen shorts in a light blue silk-linen blend and a pair of slacks from the same fabric. The wrinkles on the shorts were much more extreme, and I ended up not wearing them often because of it.
Cotton is a popular material for shorts an rightly so. No matter if you opt for cotton seersucker or khaki twill, chinos, chambray or Madras it will work well for shorts.
Polyester Blend are not recommended unless you want to exercise, run, bike…

Shorts Colors

Shorts are made for warm weather, therefore, avoid black, charcoal, and most other dark colors. Navy may work but don’t be afraid to go for lighter blues, reds (including nantcket red), whites, off-whites, beige, khaki, yellow, green, or even pink. This is a warm weather garment, and your choice of color should reflect that.

Shorts Brands

Basically, every man’s clothing brand under the sun offers some kind of shorts. Ralph Lauren has a great selection of shorts, and often they use vintage patterns from military shorts, paired with interesting fabrics and colors that are well suited for your look. As always, try to stay away from visible logos like Polo ponies. The Polo Ralph Lauren Prospect Shorts model has been around for years and it is a great timeless start but they also have pleated models as and they often pay attention to details such as ticket pockets, mother of pearl buttons, etc.
If you are looking for short, slim fitting shorts Topman or Club Monaco might be the right brand for you.
In case you prefer a preppy look, L.L. Bean, Ralph Lauren or Brooks Brothers are the more well know brands but you can also find numerous others such as Castaway, Just Madras, Blankenship Dry Goods or Southern Tide.
As always, go for quality and don’t just look for a brand.


We hope you’ve enjoyed this quick primer on summer shorts. We believe there is a place for them especially at the beach, BBQs, outdoor events, the Caribbean or in similar climate zones, when you exercise… and it’s just important you know how to wear them.
Do you wear shorts? If so, where and what styles? What are your favorite brands? Please share in the comments below.