In menswear, the clothes that truly seem to endure are the ones that offer the person wearing them some kind of function. They are literally fit for purpose. That’s the reason so many so many military pieces make the transition from the front line to the runway, and it’s also the case with workwear.

Items originally designed for carpenters, dockhands, fishermen and labourers are wearable in the truest sense of the word. They’re comfortable, layered – perfect for autumn. And, in more ways than one, they’re made to last.

“The appeal of workwear is that it doesn’t date,” says Jigsaw’s head of menswear design, Claire French. “It was never designed for a particular era or movement, so the purpose and appeal of workwear remains relevant, transcending trends.”

Functional workwear items like Red Wing boots, Dickies trousers and Barbour jackets have been fashion statements since the late 1990s and, here in the UK, were sold initially in stores like Duffer of St George and American Classics in London, and Manchester’s Oi Polloi. Workwear is now a ubiquitous on the high street and in department stores, with many fast-fashion brands even offering capsule collections of blue collar staples like chore jackets and selvedge denim jeans.

Carhartt’s Work in Progress line offers a more fashionable take on the look and is a firm favourite of fashion industry insiders. “I think it’s even more relevant right now due to the nostalgia that workwear holds towards simpler times, where people had a craft and the pace of living was slower,” says French.

Workwear offers desk-bound men a whiff of the romance of semi-skilled labour without, you know, actually having to get your hands dirty. Indeed, much of the workwear canon, especially the Americana of labels like Dickies and Carhartt, romanticises the kind of work which is being made redundant by automation or outsourcing to developing countries.

It’s no surprise that workwear’s surface textures are predominantly matte: heavy cotton drill, thick wool, deep indigo denim, butter-soft flannel, chambray, slub linen and waxed cotton. These are fabrics which neither glow or shine, or draw any attention to themselves, but are instead quietly handsome, taking on character with use and wear over time. Gloss and ‘newness’ is for the shiny world of the internet and luxury emporiums, which is what the appropriation of workwear is partly a reaction against.

The New Rules Of Workwear

Relax When It Comes To Fit

The appeal of workwear is that it is functional, so even if you’re just running for the bus or riding your bike (as opposed to making a log cabin), it quite simply works. Key to this is a loose and easy fit. Robust workwear trousers such as a pair of carpenter’s pants or raw denim jeans should ideally be worn in a more relaxed cut.

Enzo Cilenti, a designer for British workwear brand Carrier says, “Just make sure what you’re wearing is fit for purpose. For instance, fisherman trousers are cut extra wide so that they can be rolled up easily for getting in and out of the water. Make sure it’s practical.”

the best relaxed fit trousers for men

zaragaphouse of frasermatalan

Mix It Up

Unless, of course, you really are a dockhand or lumberjack, it’s best to avoid doing the whole look from head to toe. “Pair workwear with cleaner, tailored pieces to avoid looking like a pastiche,” says French. “I like the contradiction of styling a lived-in piece of vintage workwear with something sharp and polished to feel modern.”

For instance, a blue chambray or even washed denim cowboy shirt looks brilliant when paired with a tailored jacket or blazer. Equally, flipping the balance on it’s head, the right kind of jeans can provide a solid foundation for a more suited looked up top.

how to wear workwear

brooks brothersj.crewfaconnableselected homme

Toughen Your Accessories Up

A good way to channel workwear’s ruggedly masculine aesthetic is with a bit of clever accessorising. Fisherman beanies may be insufferably hipster, but they’ll keep you warm, while a solid pair of work boots keep your feet dry.

Commuters of all kinds should also look to outdoor brands for day-to-day bags that are built to withstand bad weather and even worse public transport while keeping personal belongings safe.

the best workwear accessories for men

selected hommeprimarksimonsriver island

Use Colour (Carefully)

Workwear tends to lean towards neutral shades such as navy, khaki, sand, green and brown. All of these can work worn tonally as part of a more streamlined look, but when it comes to workwear’s thicker, boxier cuts, it pays to lighten up.

“Pops of colour help break up the workwear palette,” says French. Knitwear in a bright colour, like a red fisherman jumper, with a blue chore jacket and deep indigo jeans will help to break up the outfit, making you look distinctive and different – but not too different. Workwear does its best work with a sense of cool understatement.

colourful workwear styles for men


Key Workwear Pieces

Flannel Overshirt

The flannel overshirt in red and black check is the most instantly recognisable workwear piece. Although most commonly associated with the woodsman and the lumberjack, flannel shirts were also a favourite of jazz modernists, like the saxophonist Gerry Mulligan.

Pair them with raw denim jeans or cotton khaki trousers. To soften the look, avoid work boots and try a pair of brown or burgundy loafers or chukka boots instead.

the best men's flannel overshirts

uniqlo MEN FLANNEL CHECKED LONG SLEEVE SHIRT - Click to buyj.crew Midweight flannel shirt in large plaid - Click to buyh&m Flannel shirt Regular fit - Click to buyGITMAN VINTAGE Checked Flannel Shirt - Click to buy

Cargo Pants

The nineties comeback no-one even knew they wanted, cargo pants have been a surprise re-entry to wardrobes in recent seasons, and it’s easy to see why.

A pair cut from a robust cotton, with or without pockets on the leg, should be loose fitting and hemmed up slightly, and can be worn with a pair of classic sneakers for a laid-back all-American look.

the best cargo pants for men

topman Black Ripstop Cargo Trousers - Click to buyCarhartt WIP Cotton Cargo Trousers - Click to buyORSLOW 6 POCKET CARGO PANT - Click to buyJAMES PERSE Slim-Fit Stretch-Cotton Poplin Cargo Trousers - Click to buy

Chore Jacket

The chore jacket – as worn by legendary New York Times street style photographer Bill Cunningham – expertly bridges the gap between formal and casual.

Layer it under a wool coat in the winter or over a T-shirt or sweatshirt in the summer, and you’ll have a solid smart-casual piece you can wear year-round.

the best chore jackets for men

Wallace & Barnes garment-dyed chore blazer - Click to buyUNIVERSAL WORKS MW CHORE OVERSHIRT - Click to buyPAUL SMITH BUTTON CHORE JACKET - Click to buytopman Blue Faux Shearling Lined Denim Chore Jacket - Click to buy

Worker Boots

Reassuringly sturdy work boots come into their own during the winter months, when rain and snow won’t do your loafers and ice white sneakers any favours at all.

These are best worn with a pair of raw denim jeans and a thick heavy coat, but a slightly more polished pair can also be used to bookend a suit to save your Derbies.

the best worker boots for men

ALDO Gweawien Leather Lace Up Boots In Tan - Click to buyBase London York Leather Lace Up Boots In Brown - Click to buyTIMBERLAND 6 PREMIUM BOOT - Click to buyRED WING 1907 HERITAGE WORK 6

Padded Gilet

The puffer gilet is an eminently useful bit of clothing and actually very popular among Italian men, with whom we don’t normally associate workwear.

Overseas they use it as a layering piece underneath a tailored coat or jacket, which we can’t help but commend, but it can also be worn on its own over a thick jumper or flannel shirt for an added layer of insulation.

the best gilets for men

uniqlo MEN ULTRA LIGHT DOWN VEST - Click to buyM&S COLLECTION New Down & Feather Gilet with Stormwear - Click to buymango Water-repellent quilted gilet - Click to buyriver island Black hooded gilet - Click to buy