Trends come and go, evolving and revolving with seasons and fashions. The rebel’s wardrobe is a carefully curated collection of adaptable and timeless garments.

These guides will help you build your own rebel’s wardrobe of well-made ‘rebel essentials.’ The quality pieces we recommend will outlast trends in every sense of the word. 

We’ve grouped the rebel essentials into genres based on their origins. To learn much more about the history of iconic and rebellious menswear, buy the book.

While English tailors were perfecting the bespoke suit, American tailors were hard at work creating what would be the young nation’s longest-lasting sartorial legacy.

Jeans, flannels, and work boots may have all had European roots, but they were undeniably perfected in America. In the second half of the century, American workwear would become the backbone of an emerging and enduring casual style.

Workwear includes these garments:

As the sun began to set on the Old West, the open-range cowboys, so long a familiar feature of the American Southwest, hung up their spurs.

Their campfire legends, populated with outsized heroes and outlaws, became fodder for filmmakers and songwriters, who ensured that the semi-mythic cowboy would live on in our collective imagination.

The cowboy, silhouetted against the setting sun of the Old West, looms as large as ever, casting a long shadow over rugged style.

Western includes the following garments:

Motorsports, born around the turn of the century, created a need for specialised protective clothing for riders and racers.

We owe the development of so many of the pieces in the rebel’s wardrobe to these early years of racing, when daredevils pushed rickety garage-built contraptions to the 100mph barrier and beyond.

When the rebel well and truly arrived as a style icon in the ‘50s, he came wearing biker’s leather and seated on a rumbling Thunderbird.

Motors includes:

For as long as there have been organised fighting forces, the man in uniform has cut a figure in society. Unsurprisingly, civilian menswear owes a substantial debt to soldiers and more particularly to their tailors who designed and made their uniforms.

While some pieces, like the field jacket and trench coat, have an obvious military pedigree, others, like the cardigan and the tailored men’s suit jacket, have origin stories that might surprise you.

Military garments in the rebel’s wardrobe include:

Unknowable and vast beyond comprehension, the ocean has always been a magnet for adventurers and castaways. Whether they chose the life of the sailor or it chose them, life at sea was a constant battle between man and the elements and between command and insurrection.

The clothing adopted by seafolk expresses some of this conflict. Heavy and ungovernable, it gives the mariner a style and swagger entirely his own.

Maritime gave the rebel’s wardrobe these items:

As supercharged warbirds took airborne combat to new heights, pilots were exposed to extreme temperatures in the cockpits. To protect their pilots from frostbite, military outfitters produced some of history’s most iconic and robust leather and shearling pieces.

These jackets and their nylon antecedents transitioned effortlessly into civilian style in the latter half of the century. Today, the rebel’s wardrobe is not complete without at least one jacket that was designed for American airmen.

Aviation includes the shearling bomber jackets, the MA-1, and the A-1.

Sportswear isn’t just in fashion. It is fashion. The barriers that once separated work and play have crumbled to dust, and pieces that originated on the track, field, or court have assumed their place not just on the street but in the office as well.

The suit may still be cock of the walk on Wall Street, but on Main Street, pieces originally designed by or for athletes like the polo shirt and sneakers rule the roost.

Sports includes: