In the old days (ie, around the millennium), the world of men’s bags was somewhat limited. You had a backpack, certainly, a briefcase, if you were highly business-minded, and, perhaps, a messenger bag, if you were a student, or a bike courier. Imagine, then, what Homo Sapiens circa 2003 would make of today’s bag-filled world, in which, if a man isn’t clad in matching chest rig, bum bag and mini neck pouch, he is considered decidedly underdressed, and, what’s more, underprepared.

We exaggerate, of course, but on the basis of a truth: as flexible and adaptable as we are these days, in the age of smart working and digital nomadism, our lifestyle changes also necessitate the carting around of much more stuff: gadgets, chargers, changes of clothing – and don’t get us started on the grooming regimen. In light of this state of affairs, we thought it high time to round up some of the very best bags currently on the market, below, which should come in handy whether you have travel plans in your immediate future (though, ahem, we’re guessing not) or you’re simply looking to rationalise your complicated, connected life.

Some people don’t like to be weighed down. Yes, they’re probably the same kind of people that like to wear bucket hats and sandals. It’s just this kind of person that, at the moment, is having something of an unlikely fashion renaissance: blame the fact that the 1990s have, as of late, become a lightning rod for our culture’s ravenous sense of nostalgia. Or roll with it, and complete the look, bags included. Of course, such a free soul is not going to travel with a boring old black suitcase – they need something with a bit of weathered personality, such as this case from Crash Baggage. The Engineered Garments tote offers an all-natural colour palette with the benefit of sturdiness, thanks to its ripstop cotton fabrics, while the LOEWE neck pouch is the perfect size for your phone and wallet.

Wilderness adventures, even if the adventure is only travelling to a friend’s cabin in the woods, require hardy gear. Filson makes just the suitcase for such trips. It’s soft so you can shove it into the already overstuffed boot of a car, but made of abrasion-resistant, ballistic-grade 1,000-denier CORDURA, which means no ripping and tearing. Make sure you bring along a backpack for weekend hikes. This one from Indispensable will look as good on a trip into town as it will in the hills. We’ve styled each bag to match an item of clothing (Filson to fleecy sweatpants, Indispenable to fleecy vest), which, we think, adds a little intentional something to a travel day. Take note.

When travelling for business, it’s (unfortunately) not unusual to run into colleagues sleepily purchasing snacks in the airport before a 6.00am flight. Which is why we recommend putting a bit of thought into your airport outfit – smart sweatpants, a clean-cut sweater and box-fresh sneakers will do just fine. What you wear when you land is a different story, and we strongly suggest you pack smart so your clothes aren’t rumpled and creased. This unbelievably sleek aluminium and leather trimmed suitcase from Fabbrica Pelletterie Milano is nice and roomy and will keep your togs in good order. The case has brown leather straps (in the same hue as the handles) inside to encourage tidiness. Use them to your advantage.

Three bags? Yes, three bags are perfect for a trip into the city for a voyage of cultural discovery. You never know what you might need, which is why bringing plenty of bags for gifts, souvenirs and changes of clothing is a good idea. Start by packing breakable items, or things that should be kept neatly folded in this Horizn Studios polycarbonate carry-on. Soft things such as sweaters and pyjamas can go in the Porter-Yoshida & Co duffel. Finally, books, laptops, guide books, maps, etc, can all slip into a Neighborhood tote bag. Wherever this trip takes you – the museum, the gym, a cocktail party – you’ll be ready. Sometimes overpacking is underrated.

A weekend in the British countryside or on a sprawling ranch upstate calls for an elegant holdall. This one, from Bleu de Chauffe, is made from full-grain leather and tanned using natural agents to achieve a worn-in patina. A leather duffle is an adult upgrade from the nylon version of your teens and early twenties and immediately lends your travel get-up a stately appearance. It looks rather jaunty carried in the hand, but it also has a shoulder strap for when you need to purchase coffees and pastries for your fellow travellers and then run for the train.