5 Workwear Outfit Combos That Never Fail

It would be wrong to call workwear a trend. Trends come and go, they’re routinely ridiculed and, building an entire outfit around one is never – repeat: never – a wise move.

It’s better to think of it as one of menswear’s undying perennials, as reliable as tailoring and as comfortable as sportswear. Workwear provides the foundations of the hardiest corner of your wardrobe, responsible for your go-to jeans, toughest boots and favourite chore jacket.

Not that you have to wear them all at once. Workwear plays nice with lots of different styles, but it’s heavily enough ingrained in the way we dress that’s it’s also possible to base an entire outfit upon it without getting yourself laughed out of the pub. With other cornerstone garments like overshirts, beanies and flannel shirts in the same stable, this is one of the most wearable aspects of menswear – provided you know how to style it, that is.

Carhartt at ASOS

To help you piece together a workwear wardrobe without looking like you bulk order your clothes from a building-trade supplies catalogue, we’ve thrown together some workwear outfit ideas that cover a range of plans, dress codes and weather patterns.

From modern, streetwear-inflected, utilitarian cool to the tried and tested plaid-shirt-and-jeans combo – here are five failsafe ways to wear menswear’s toughest clothes.

Weekend Woodsman

Contrary to popular opinion, “lumbersexual” isn’t all a load of ironic, beardy hipster codswallop. Shave off the flavour saver, lose the wire-framed specs and what you’re left with is perfectly serviceable casual dress, fittingly tailored for tackling those troublesome transitional months.

This outfit relies on some of our favourite workwear staples: the plaid shirt, a pair of sturdy leather boots, some quality denim and a gilet. The reason we like them so much is because of their versatility. Yes, these garments look great worn together, but they also work well with the rest of your wardrobe. They’re pieces you can keep coming back to again and again.

In terms of styling, the shirt should be nice and thick, while the jeans need to have a wide enough leg to accommodate the boots. That means steering clear of slim or skinny cuts and opting for straight-leg or relaxed instead.

On your feet, it’s worth investing to get something that will last. In our experience, heritage American brand Red Wing makes some of the best work boots to be found.

French Working Blues

For concrete evidence of just how stylish a nation France is, look to the fact that even the labourers over there are trendsetters. The rich blue colour and patch-pocket detailing of the French chore jacket has made it one of the most recognisable pieces in the world of workwear, as well as an invaluable addition your outerwear rotation.

The jacket’s casual styling makes it a great way to add a splash of colour to anything from a T-shirt and jeans to tailored pants and dress shoes. However, if you want to stay true to its European roots, teaming it with a rollneck sweater and white canvas pumps is a good way to go.

In terms of fit, the jacket shouldn’t be too snug, but shouldn’t be shapeless and boxy either. Aim somewhere in the middle and you can’t go far wrong. Same goes for the trousers. Go for a relaxed cut with a wider leg opening and cuff the ankles a couple of inches above the top of your shoes.

Mountain Man

“Fleece” and “cargo trousers” may have been some of the dirtiest words in the menswear lexicon until recently, but in the world of workwear, they’ve always been cool.

These practical pieces are built for braving the great outdoors, and thanks to their recent acceptance into mainstream men’s fashion, you no longer have to be a vegan tree surgeon from Cornwall to get away with wearing them in public.

Lately, outdoor brands have been trawling their archives for inspiration. This has resulted in some fantastic throwback fleecy goodness from the likes of Patagonia and The North Face. Investing in one of these retro warmers is a good way to embrace fleece in style and teaming one with a pair of cuffed, loose-fitting cargos makes a great outfit for tackling chilly Sundays in style.

Add in a pair of suede hikers and a beanie, and enjoy the paradox of being cosy and cool all at the same time.

Double Denim

Denim: surely workwear’s greatest export. This hard-wearing wonder fabric was developed with the express intention of withstanding anything a day in the workshop could throw at it, and has since become one of the most popular materials in modern menswear.

Despite its practicality and good looks, there are those who will tell you that wearing denim top and bottom is a cardinal style sin. This rule is about as outdated as the idea that jeans are strictly for manual labour and wearing a pair casually is some sort of rebellious statement.

The fact of the matter is double denim can work. Not only that, but pulling it off is a surefire way to earn yourself some major style points. The best part is it’s not even that difficult to do.

The key is going for either contrasting or matching shades. Having two different shades that are too close to one another is where things start to get nasty. Keep your washes simple too. That means no distressing or complex colours. Your best bet is to stick to either dark shades or stonewash and keep the rest of your outfit simple and stripped back. Throw in a pair of chukka boots to score some additional workwear cool points.

Japanese Workaday Streetwear

If there’s one nation that really embraced the whole workwear thing, it’s Japan. Not only did Nippon adopt the look, but it made it its own, taking utilitarian style in bold new directions, with pockets, straps and baggy fits aplenty.

This uniquely Japanese fusion of workwear and streetwear is evident in the output of labels like WTAPS, Cav Empt and Visvim. Although you don’t need to pay those sorts of prices in order to get the look.

Starting from the ground up, a pair of classic canvas sneakers is a good jumping off point. Go for Converse Chuck Taylor ‘70s or a Vans Sk8 Hi for a dose of throwback goodness. Legwear-wise, choose something with plenty of pockets and a relaxed cut – camo cargos if you’re feeling brave, army fatigues if you’re not.

Up top, a baggy hoodie lays a solid foundation, especially when worn layered over an even baggier T-shirt. Then, tie it all together with a utility vest and some suitably street-friendly headwear.