Stop Chasing Trends and Start Investing in These Through Line Pieces
When researching for our book, The Rebel’s Wardrobe, we looked through thousands of photographs of the twentieth century’s most stylish rebels.
We noticed that, while fashion trends came and went, stylish rebels (past and present) gravitate to the same rugged pieces.
Together, these pieces form a kind of through line that connects the rugged rebels of every age to each other. It’s what would allow us to drop a mid-century rebel like James Dean or Marlon Brando into the middle of Times Square today (or any other day) without them seeming out of place.
These pieces aren’t just stylistic curiosities that have held out interest. They’re assets in any wardrobe, and they’re worth investing in.
Why Invest in Timeless Pieces
Well-made clothing is an investment, and any investment is a gamble. It’s relatively easy to justify a modest spend on an on-trend item, but, as with any small stake, the pay-out is fleeting. There’s a quick sugar-rush-like high, and then we’re on to chasing the next trend.
The through line pieces—especially when they are well-made—are appreciating assets. They age slowly and gracefully, repaying their investment not in novelty but in longevity.
Cuts and scars might consign an on-trend piece to the rag heap. For the well-made through line piece, though, signs of wear and tear are badges of honour, conferring rather than subtracting value.
New to Rugged Menswear? Start with Jeans, Tees, and Boots
Telling you to invest in a great pair of selvedge jeans, some quality tees, and a pair of sturdy leather boots is likely to be advice you’ve heard before.
But if you’re new to this scene, or just want to brush up on the basics, start your hunt with these guides:
The Timeless Ten: Menswear’s Through Line Pieces
These ten through line pieces form the backbone of a rugged, enduring wardrobe. They cover workwear, military, Ivy League, and naval tradition. Different origins. Same through line.
The list in hard-wearing shirts like the chambray and the heavy flannel; outerwear staples like the peacoat, the denim jacket, and the M-65 field jacket; underdogs like the rugby shirt, the Breton, and penny loafers; the fisherman’s sweater; and, finally, the crew neck sweater that starts it all.
MENSWEAR CLASSIC #1
The Grey Crew Neck Sweatshirt
In 1926, Bennie Russell was a varsity quarterback at the University of Alabama. The wool sweaters the team practiced in were hot, itchy, and difficult to launder, so he asked his father, founder of Russell Manufacturing Co., to make him something better suited to athletics.
His father responded by producing a heavy version of the long-sleeved cotton shirt his company was then making for women. Athletes flocked to the sweatshirt, quickly making it a fixture on tracks and fields around the country.
Following the war, when campuses took a turn towards a more casual collegiate style, the sweatshirt (often with the flocked lettering pioneered by Champion) became one of the defining pieces of Ivy style–a key point of inspiration for Japanese designers.
Most of us have at least a few inexpensive sweatshirts kicking around in our wardrobe already. The difference between these mass-produced sweatshirts and the genuine article can’t be fully appreciated until you’ve worn one of the latter. Definitely worth investing in.
While sweatshirts are available in nearly every imaginable colour, it’s the classic grey, with its long athletic and casual pedigree, that belongs in every single wardrobe. Our favourite versions are produced in Japan, Germany, and Canada.
Our Favourites Crew Necks:
MENSWEAR CLASSIC #2
The Chambray Shirt
It wasn’t until early in the twentieth century that the button-up shirt as we know it began to emerge. Until then, the buttons on a shirt would terminate around the sternum or navel. Shirts would be unbuttoned and then pulled over the head.
“Jacket-style” shirts, which unbuttoned all the way to the waist, quickly crowded pull-overs out of the market, setting the stage for the emergence of a true-blue American workwear icon: the chambray shirt.
In the 1920s and ‘30s, American brands like Big Yank, Montgomery Ward, and Hercules produced chambray work shirts that became a kind of unofficial uniform for the working man. Soft, durable, and easy to launder, chambray work shirts are the original “blue collar” shirt.
Over the last century, chambray has worked its way into nearly every facet of menswear. A close cousin of denim, the fabric is at its best when approached reverently and nostalgically by heritage brands that respect the shirt’s long lineage.
In either work or western versions, chambray shirts are a no-brainer. They pair brilliantly and easily with selvedge denim. They look great when new, but they really come into their own when they’ve been washed down and baked in the sun.
Our Favourites Chambrays
Or find your favourite in our in-depth chambray guide here.
MENSWEAR CLASSIC #3
The Rugby Shirt
The rugby shirt is equal parts gentility and brutality. With its white collar, buttoned placket, and often-vibrant school colours, it betrays some of its origins in England’s upper-crust public schools. At the same time, it seems to cry out for collision and carnage.
The bone-rattling sport was born in England in 1823 at Rugby School in the West Midlands. At first, players wore white collared shirts and matching trousers. It was utter chaos for spectators, with nothing to distinguish the players from each other other than knit caps (one team would wear red, the other blue).
When English footballers started wearing vertically striped cotton jerseys, rugby players followed suit, opting for collared jerseys with brightly coloured horizontal hoops that helped distinguish them from footballers but, more importantly, from each other.
They were worn almost exclusively as a display of school and team spirit until English rebels like Mick Jagger and Oliver Reed started wearing rugby shirts in whatever colours pleased them. This helped permanently shake the rugby shirt loose from its academic and athletic roots.
To lean into the rugby’s rough and tumble reputation, wear it slightly askew. Unbutton the placket and let the collar roll or stick out at awkward angles. Don’t iron it into shape or cover it with layers. It’s a rough and tumble shirt. It doesn’t need much help.
Our Favourite Rugby Shirts
MENSWEAR CLASSIC #4
The Peacoat
Double-breasted and made from extremely heavy wool, the peacoat was for centuries the sailor’s best foul-weather friend. While Dutch sailors pioneered the design in the eighteenth century, it was English and then American sailors who made it iconic.
Sailors adored the peacoat. The double-breasted jacket could be fastened across the body in either direction (depending on which way the wind is blowing), and the handwarmer pockets sit high on the body. Thrust your hands in the pockets and the jacket tightens around you.
The jacket’s most striking feature—its large ulster collar—can be turned up and, in particularly nasty weather, fastened with a throat latch. The turned-up collar not only keeps the throat warm, it also frames the face brilliantly—an unmatched combination of substance and style.
After WWI and WWII, sailors made landfall with their peacoats tucked under their arms, and these jackets (along with mountains of surplus and civilian versions) quickly became a go-to piece of outerwear for style-conscious rebels on both sides of the Atlantic.
The best modern versions of the peacoat capture all of the brawny brilliance that made the piece such a formidable opponent. With extremely heavy melton shells, large collars, and corduroy-lined pockets, they’re ready to do battle with the elements. Turn the collar to the wind and set sail.
Our Favourite Peacoats
Want more options? Visit our guide to naval jackets here.
MENSWEAR CLASSIC #5
The Penny Loafers
Around the end of the nineteenth century, wealthy English fishermen flocked to the Norwegian fjords looking for the world’s best fishing. The Lords of Salmon returned to England with more than just their catch. They adopted a leather slip-on the Norwegians called the teser shoe.
One Norwegian shoemaker, Nils Tveranger, who had apprenticed as a shoemaker in Boston before WWI, saw an opportunity and, incorporating a moccasin-style gathered toe stitch, introduced the first recognisable penny loafer.
His shoes spread among the upper classes in England, making the rounds at exclusive resorts on both sides of the Atlantic. In Palm Beach, the shoes were spotted by the founder of Esquire magazine, who quickly partnered with G.H. Bass to produce Weejuns (a nod to the shoe’s Norwegian roots).
Inexpensive and stylish, the shoes were quickly adopted by young Americans, who began pairing them with jeans and white socks in the ‘40s. The “sloppy look” as it was dubbed at the time started with young women, with men quickly following suit. American college students gave the shoe its most enduring name when they started slotting pennies into the vamp sometime in the ‘50s.
Selvedge denim and penny loafers make for a combination as dynamite as ever, and the shoes make an ideal alternative to boots in the summer months. Invest in a good pair and they’ll age and patinate brilliantly. The very definition of casual elegance.
Our Favourite Penny Loafers
MENSWEAR CLASSIC #6
The Heavy Flannel Shirt
Originating as a kind of coarse and heavy overshirt worn by sixteenth-century Welsh farmers, flannels found their true calling in the boreal forests of the American north. Warm, rugged, and highly visible (a key safety feature), flannel shirts and jackets became a kind of uniform for American and Canadian loggers.
In 1850, Woolrich Woolen Mills made their first foray into the garment game with the now-distinctive red and black buffalo plaid. When stories began to circulate about a mythical, larger-than-life logger named Paul Bunyan, he wore the logger’s uniform: jeans, suspenders, and the buffalo plaid flannel.
Pendleton performed a similar trick when, in 1924, they debuted their first Virgin Wool Shirt. While flannels and working cowboys were hardly strangers, Pendleton’s plaids caught fire in the western scene. By the middle of the century, Pendleton’s plaid wool flannels were everywhere.
From the surf scene of the ‘60s to the grunge rockers of the ‘90s, from field and stream to campus and coffeehouse, plaid flannels, made increasingly from brushed cotton rather than wool, worked their way into the very heart of American culture and its countless subcultures.
As selvedge denim weights climbed in the early aughts, flannels packed on the pounds as well. Today, extraordinarily heavy flannels are a staple of the heritage scene. Virtually indestructible, these heavy flannels are as essential as they are immortal.
Our Favourites Heavy Flannels
There are a lot of great heavy flannels out there. You’ll find the best of the best in our flannel guide.
MENSWEAR CLASSIC #7
The Type II or Type III Denim Jacket
Levi’s first version of the denim jacket was a simple, utilitarian design. A boxy fit with just a single chest pocket, the Type I as it was called later lasted for half a century, serving the needs of American farmers, miners, cowboys, and factory workers.
By the end of WWII, though, denim was heading in new directions. No longer merely a working man’s fabric, denim had a mile-wide rebellious streak. Sensing a shift in their market, Levi’s updated their denim jacket, trimming some fat and adding a second chest pocket to make it more symmetrical.
The resulting Type II jacket, which debuted in 1953, gave double denim looks an altogether new kind of sex appeal. With the help of rebel icons like Elvis Presley and Eddie Cochran, the new breed of denim jacket (and the rebels who wore it) defied authority and convention.
Levi’s completed the hat trick in 1962 with their Type III. Born iconic, the Type III, with its trimmer cut, higher chest pockets, and vee-shaped stitches running from the pockets down to the waist, became the de facto denim jacket for the generation that would change everything.
The legacy denim brands lost some of their magic touch when denim exploded as a global consumer staple, but Japanese denim purists pulled American workwear back from the brink. Their versions of the classic denim jackets capture some of the magic that help make the originals eternal and are well worth investing in.
Our Favourite Denim Jackets
A good denim jacket is a must-have for any serious denimhead. We’ve rounded up all our top pick in this guide.
MENSWEAR CLASSIC #8
The Fisherman’s Sweater
Our appreciation for the combinations of indigo and cotton runs bedrock deep, but wool isn’t far behind. We know from experience, when it comes to that long battle with the elements that is the Scandinavian winter, wool is a true wonder.
Atlantic fishermen have long understood this. The classic fisherman’s sweater, likely originating in Guernsey, one of the Channel Islands between England and France, was a tightly knit and slim-fitting sweater made from oiled worsted wool.
Often knit for fishermen by their wives or mothers, the typical fisherman’s sweater would require around 100,000 stitches, taking months to complete. It would be knit symmetrically so that it could be worn with either side facing forward–crucial when dressing in the dark or in a hurry.
The sweaters became a kind of folk art in the fishing communities up and down the Atlantic coast. Patterns were passed down from mother to daughter. Rarely recorded, they were stored in the muscle memories of generation upon generation of the hardy and patient women of the North Atlantic.
The sweaters first became commercially available in the ‘30s and ‘40s, and, with the help of early adopters like Grace Kelly and Elvis Presley, they quickly became a wardrobe essential. Buy a good one in a classic colour (dark blue or cream) and you’ll only ever need one.
Our Favourite Fisherman’s Sweaters
These are just the tip of the iceberg. Dive deeper with our guide to fisherman’s sweaters.
MENSWEAR CLASSIC #9
The M-65 Field Jacket
Militaria slips in and out of style, often playing around on the margins of the mainstream when it’s not enjoying a strong resurgence. The M-65, though, has managed to transcend trends. Since its debut in the ‘60s, it has remained on the front lines of style.
The field jacket issued to American soldiers during the Vietnam War was the culmination of a long period of development. Its popular predecessors, the M-43 and M-51, had served soldiers well in WWII and Korea, but jungle warfare in Vietnam demanded an updated jacket.
Alpha Industries, makers of the iconic MA-1, won the bid to redesign the field jacket. They piled on the innovations, adding a NYCO (a nearly indestructible nylon-cotton blend) shell, a detachable liner, and, most iconic, a zippered collar that concealed a water-resistant hood.
When soldiers returned to American shores, it was to a changed America. Battle lines were drawn, and the M-65 found itself on both sides of the conflict. The jacket became a blank canvas, changing meaning radically depending on how it was embellished and worn.
With its striking and immediately recognisable silhouette, the M-65 has won legions of new admirers and adopters with each new generation. From Travis Bickle and Frank Serpico to John Rambo and Public Enemy, the M-65 hasn’t lost a single ounce of its defiant attitude.
Our Favourites M-65 Jackets
MENSWEAR CLASSIC #10
The Breton
The sun never sets on the Breton. Perpetually basked in a continental beachside glow, it raises the temperature slightly in every room it enters.
The most essential feature of the breton (called a marinière or tricot rayè by the French) is the pattern–dark blue stripes on a white background. While most modern versions are cotton, the original was wool, and it was worn by French fishermen in Brittany (in northwest France).
The French Navy made the breton the official uniform of French sailors in 1858. Short in the sleeve and wide enough in the neck to expose the collarbones, the shirts were easy to get on and off, even when wet, and they made sailors easy to spot in the rigging.
With the help of Coco Chanel, the iconic stripes became a fixture on continental beaches following WWI. At the same time, it flexed its muscle on screen, with brawny actors like John Wayne, Kirk Douglas, and Marlon Brando all showcasing the breton’s rugged potential.
While there are literally thousands of shirts that look the part on the market today, there’s a big difference between horizontally striped shirts and true-blue bretons. Look for something traditional–preferably made in France. When the sun comes calling, you’ll be glad you did.
Our Favourite Bretons
Want to Explore Beyond the Timeless Ten?
Most of the pieces above are explored in depth in The Rebel’s Wardrobe, where we trace the history of more than 40 menswear icons—from denim jackets and peacoats to Breton stripes, penny loafers, and beyond.
The book examines how these garments emerged, evolved, and ultimately earned their place as menswear classics. You can get a copy here.
But the education doesn’t stop with the book. If you’re ready to invest, explore our buying guides for jeans, jackets, boots, and other staples here. And if you want to understand the craft—dyeing, weaving, construction, and fading—our in-depth denim knowledge section breaks it all down.
Different entry points. Same through line.
Understand the Details That Matter
I’m Thomas, founder of Denimhunters. I write emails that go deeper into denim—how jeans are made, why details matter, and how to make better choices without the noise.
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