For the past few years messenger bags have been skulking around the fringes of menswear, playing second fiddle to backpacks (hyper functional) and totes (hyper fashionable), all the while feeling generally unloved and neglected. The humble messenger bag may not boast the hands-free, even weight distribution of a rucksack but, to its credit, it’s far less likely to piss people off on the commute.

And, for all that rakish charm the tote has up its sleeve, the messenger bag will let you multitask much easier. Ever tried holding a tote, reading a book/your phone and gripping onto public transport for dear life at the same time?

The trouble with the messenger bag is its reputation among men who grew up with tatty versions at school. You know the ones: bursting at the seams with books, files and PE kit. But don’t shoot the messenger. Just as the backpack has been reimagined for the male population who’ve grown out of school uniforms, with a little bit of digging, you’ll find that this style of bag can score highly on practicality and menswear cred.

What To Look For In A Messenger Bag

When it comes to choosing the perfect messenger bag, size is (almost) everything. Choose one that’s too big and you’re well on your way to looking like a postman at the start of his shift. Too small, on the other hand, and you’re in prime roadman territory (if you’re too old to know what one is, trust us, it’s not a look that you want to emulate). The ideal dimensions? A couple of inches wider than a sheet of A4 paper in all directions.

If you want a messenger that’ll last, go for a black, brown or navy leather design with a full lining and swerve classic bag mistakes like bold patterns or slogans, which have the tendency to date faster than milk left in the sun. Oh, and don’t forget to check your bottom: a messenger with a reinforced base and studs offers increased durability and therefore longevity.

Convinced that cross-body is the way to go? Then look to the following brands, who make messenger bags the way we like them: quality fabrics, functional design and finishing touches that are way too cool for school.

Want Les Essentiels

When it comes to minimal luxury, American (yes, really) brand Want Les Essentiels De La Vie comes up trumps.

Proving that everything stateside isn’t necessarily bigger or brasher, the label swerves in-your-face design for a sleek and timeless approach that will never go out of style.

Buy Now: £375.00

Want Les Essentiels

Sandqvist

Nordic countries have an annoyingly persistent reputation for doing almost everything cooler, simpler and slicker than the rest of us. Lo and behold – Swedish accessories brand Sandqvist is no exception.

Hold the eye-roll though. For those who have the messenger bag down as terminally naff, the label’s collection of staggeringly tasteful designs is the messenger’s mic-drop moment.

Buy Now: £155.00

Sandqvist

John Lewis

British department store John Lewis does an excellent line in not-boring commuter accessories. Its Italian-made own-brand messenger bags are a prime example: smart enough for the office but suave enough for a 6pm bar stop.

It also stocks a series of well-respected third-party brands, including the likes of Eastpak and Barbour, and operates a price-matching policy if you find the same product cheaper elsewhere.

Buy Now: £105.00

John Lewis

Smythson

If you needed any more proof that the messenger bag isn’t just for the captain of the Year 11 debating society, look no further than British brand Smythson whose discreet luxury designs are way beyond the reach of sticky-fingered school kids.

For the man who has money to burn, but isn’t interested in broadcasting it to the world, investing in a Smythson bag is the stealth way to upgrade your arm candy.

Buy Now: £995.00

Smythson

Paul Smith

Paul Smith has long been flying the flag for (measured) British eccentricity, irrespective of whether or not it’s deemed ‘in’ at any given moment, so it’s no real shocker that alongside classic, work-safe messenger bags the label offers plenty more daring designs.

A bit of print here, some contrast piping there, a motif or two for good measure – you can go as incognito or out-there as you see fit.

Buy Now: £450.00

Paul Smith

Mulberry

Trend enthusiasts and those who love timeless classics are often considered to be of divergent tastes, but Mulberry’s high-end messengers prove that there is some common ground to be found between these warring sides.

Offering precise craftsmanship, premium construction and heritage-meets-modern design, the brand’s bags look stylish, wear well and won’t date while the rest of your wardrobe ebbs and flows.

Buy Now: £750.00

Mulberry

Herschel

Canadian brand Herschel is less than a decade old, but its technical prowess and stellar reputation give the impression of a much longer history.

Crafted from hardy woven fabrics, the label’s messengers are ideal for the man who wants to look presentable but hasn’t got the inclination to be precious about where he dumps his bag. And with most coming in at under £75, it’s hard to get precious about the price too.

Buy Now: £65.00

Herschel

Ted Baker

Ted Baker has made its name sitting in that under-occupied sweet spot between high street and high end, managing to be aspirational yet approachable.

The British brand’s messenger bag collection is proof: the style is aspirational (check out its luxurious pebbled leather options) while the price is most definitely approachable. The perfect compromise.

Buy Now: £89.00

Ted Baker

J.Crew

Mixing its signature preppy aesthetic with quality construction, J.Crew produces the type of bags you would expect to see carried by the Ivy League elite.

Featuring internal and external pockets, brass hardware and collar stud closures, the American brand’s messengers are both stylish and practical, often crafted from durable waxed cotton to ensure your valuables don’t get soaked through in the rain.

Buy Now: £100.00

J.Crew

River Island

The great thing about River Island is that no matter how many things you add to basket, your total never seems to add up to anything that would give your bank manager cause for concern. The high-street retailer’s messenger bags are no exception to this rule, and pleasingly they also punch well above their weight for the price.

Expect a range which flits between classic and trend-led, with most giving you change from £30. That, quite frankly, is an utter steal.

Buy Now: £25.00

River Island

Timberland

Not content with stamping out all competition for the title of ultimate worker boot, purveyor of outdoors apparel Timberland want to help you out with your baggage too.

Built for function first and foremost, the brand’s messenger bags are sturdy pieces of kit designed to last, but crucially they also score highly in the style stakes and are great value for money.

Buy Now: £45.00

Timberland

Eastpak

Before you get all incredulous, bear with us. Eastpak may have helped you and your peers lug round your school kit way back when, but (like you, hopefully) the brand has grown up, moved with the times and now produces a wide range of messenger bags that are suitable for adults, too.

Putting practicality front and centre (the majority are crafted from a ‘life-resistant’ fabric), you will find every colour and pattern you could wish for in this wide-ranging collection.

Buy Now: £55.00

Eastpak

Tommy Hilfiger

An appreciation of nostalgic design meets modern construction at Tommy Hilfiger, a brand whose bags riff on its glory decade (the 1990s) while adding a bang-up-to-date lick of paint.

Much like Donald Trump, these messengers are unapologetically American (often coming in a palette of red, white and blue), but unlike Trump they go heavy on good taste and low on gaudiness.

Buy Now: £63.25

Tommy Hilfiger