4 Lessons You Can Learn From Classic American Workwear

a man wearing a white t-shirt

A man wearing classic American workwear | Pablo Cuadra/Getty Images

They’re everywhere in the U.S.’s hippest cities: guys sporting jeans that wouldn’t look out of place on cowboys or coal miners, jackets evocative of lumberjacks and farmers, sweaters originally designed for sailors, shirts reminiscent of ranchers in the American West, and, quite often, full beards, slick classic haircuts, arms full of tattoos. For years, an ever-widening circle of menswear devotees has looked to the tradition of hard-wearing American workwear for style inspiration.

While it might seem odd, at first, that clothing styles first made in the 1800’s and 1900’s would be at the center of a modern trend, the popularity of heritage workwear is about something more than style. The denim-clad guys wearing these styles are attracted not just to the aesthetic of the clothing, but to workwear’s ability to evoke an era in which things were made to be used and to last. We don’t recommend romanticizing that era — after all, many styles we love trace their roots to decades marked by injustice, economic depression, and social problems. But we think that you can appreciate the tradition of American workwear, one that’s just as alive among people who like wearing quality clothing as those who like making it.

Many clothing companies making workwear-styled apparel still use superior materials, traditional manufacturing methods, fine craftsmanship, and excellent attention to details — which is exactly what you want when you need to look sharp but stay comfortable on the travels and adventures you have planned. Getting workwear right is about details. Clothing makers who get those details right build clothes that last, and guys who choose the right details look classic and cool — not like they’re wearing the blogger-approved trend of the week.

1. Make the garment — and its material — your own

Raleigh Denim Workshop Jones denim

Men’s denim | Raleigh Workshop

One of the greatest things about workwear is that it’s constructed to be worn extensively and to wear in beautifully. Nowhere is that more apparent than in a good pair of jeans — particularly of the rigid, selvedge variety — which start out uniformly dark and gradually wear in, acquiring fading and honeycombing that reflect how you wear your jeans. A worn-in pair of rigid jeans becomes an incredibly unique and personal piece of clothing, and many guys wear theirs with a sense of pride in how they’ve made the fabric their own through many hours of wear.

When shopping for a pair of jeans that will only look better if you wear it day in and day out, you’ll ideally want to look for rigid, also called raw, denim, which in many cases also has selvedge, the finished edge of the fabric you see when the denim is made on traditional, narrow shuttle looms. Raleigh Denim Workshop, which makes the pair above, is an excellent destination for such jeans, as are other American brands like Railcar Fine Goods, Imogene + Willie, Tellason3Sixteen, and Earnest Sewn.

2. Choose clothing that combines form and function

Filson Mackinaw Cruiser jacket

A flannel jacket | Filson

Outerwear is one of the key pieces where you should look to traditional workwear for inspiration. You have a wide variety of vintage-inspired choices, which enables you to choose a piece that’s both very functional for your lifestyle, and appeals to your sense of style and aesthetics. Workwear is all about shorter jackets and coats, which afford you an easier range of motion even when wearing a number of layers.

Choose a short peacoat if you’re looking to choose a military and nautical classic. Choose a wool field coat if you want a wool jacket that’s more for the field than in-town. Choose a tin cloth or waxed canvas jacket if you’re searching for something to repel the northeastern rain or northwestern mist. Look for a fisherman’s mac if you’re anticipating a season of heavy rain. Or look for a cotton chore coat if you live in a warmer state, but still need an extra layer for chilly mornings. Good places to begin the search for the perfect jacket include Filson, which makes the classic Mackinaw cruiser above, or Cockpit USA, OrvisSchott, and Hand-Eye Supply.

3. A good pair of boots will take you the extra mile

Oak Street Bootmakers trench boot in natural Chromexcel

Men’s boots | Oak Street Bootmakers

There was a period in American history when just about every hard-working man wore a pair of boots everyday. In some professions, that’s still true today. But even if your 9 to 5 doesn’t require the same kind of workwear that miners and ranchers wore, you can still find a pair of boots that can become your new go-to footwear. If you go for a traditionally-styled pair with a leather upper and a leather sole (or unobtrusive leather sole), you’ll be able to wear them with dressed-up ensembles and with casual ones.

When shopping for a pair of boots, look for brands that still use excellent leather, top-of-the-line craftsmanship, and classic styling. Your options range from work boots to chukka boots to dress boots, and you can find excellent American-made options to fit every aesthetic. Some of our favorite American brands include Oak Street Bootmakers, which makes the gorgeous trench boot above, in addition to all-American classics like Red Wing, Wolverine, Alden, and Rancourt.

4. Choose fabrics that are appropriate to the season

Mister Freedom utility chambray shirt

Men’s chambray shirt | Mister Freedom

Because workwear is about practicality, it’s important to realize that your ideal wardrobe, and your daily uniform, are going to change with the weather throughout the year. An easy illustration of the principle is how your lineup of button-front shirts should change as the weather gets colder in the fall and winter. Among workwear devotees, the button-front shirt is both effortlessly stylish and undeniably functional, especially since the sleeves are so easy to roll up when there’s messy work at hand. After all, your clothes should never get in the way of what you’re doing.

Guys taking cues from traditional American workwear have their pick of shirts made from warm and hard-wearing fabrics — everything from denim to chambray, flannel to brushed cotton, and twill to chamois cloth. Some top destinations for shirts that can stand up to some abuse include Mister Freedom, Gitman Vintage, Engineered Garments, Taylor Stitch, Apolis, and L.L. Bean Signature.