I watched a man at a fitting room the other week argue with a bag. He loved the colour. He hated the weight. He kept opening and closing the zip like he was trying to convince it. That’s the problem with buying a bag off impulse β nobody thinks about what actually goes inside it.
A good bag is the closest thing a man has to a one-purchase-for-life item. Buy it right and it carries your laptop, your gym kit and your Tuesday-night-into-a-weekend plans for a decade. Buy it wrong and you’ve got a limp, quarter-full holdall looking sorry for itself. Here’s how I’d edit the decision, the way I’d edit a closet: function first, aesthetics second.
Size: what’s actually going inside?
Size matters more than any brand name. Ask yourself one question: what is this bag’s primary job?
- Documents and a tablet? A folio or small briefcase. Stop there.
- Gym kit by day, carry-on by night? A weekender.
- Cycling to work, hands free? A messenger.
Pick the size for the job, not for the photo. A bag stuffed full enough to scale Everest is no bag at all β it’s luggage you forgot to check.
Colour: boring is a feature
Treat a bag as a timeless purchase. For your first one, work in what you already own: darker browns and black cover both the office and the weekend without a second thought.
Once you’ve got that base, modern neutrals are where it gets interesting β tan, grey, navy, khaki, burgundy. They don’t date the way trend colours do. I don’t say ‘millennial pink’ and mean it as an insult, but a bag has to outlive the palette of the season it was bought in.
Material: the three that work
Leather
Real leather ages. That’s the whole argument for paying up: genuine hide develops a patina, gets more personal with every use, and outlives the imitation stuff in a way you can see. It’s the right call for a briefcase, and honestly for almost anything you want to keep.
Two caveats. Leather isn’t breathable, so it’s the wrong choice for sweaty gym gear β the lining will hold the smell, and it’s as bad as it sounds. And if your day-to-day is casual, canvas or nylon may serve you better than something that reads too formal.
Canvas
There are two kinds, and they’re not the same. Fabric canvas is a thick woven cotton β low cost, widely used by high-street brands, fine for a casual backpack or tote. Coated canvas is cotton with a PVC finish: hardwearing, scratch-resistant, often waterproof. That’s what the luxury houses use, from Gucci to Louis Vuitton, and the reason their bags shrug off rain.
On a budget, a classic cotton canvas bag that can take a beating is the smart buy.
Nylon
Nylon is the middle path, and it’s where a lot of modern menswear has landed. The finish gives it a premium feel, it’s durable, it’s light to carry for hours, and it works with tailoring and casualwear equally. Ballistic, ripstop, waterproof β the technical range is wide, and the modern fabrics are built to last.
Details and hardware: where quality shows
The things people skip are the things that tell you whether a bag is good. Look for sturdy metal buckles and fastenings, reinforced stitching where the handles join the body, quality zips β YKK is the name that’s widely considered the best β leather piping and protected corners, and a reinforced bottom.
Practical side: internal pockets and compartments, a padded section for a laptop, adjustable padded straps, a breathable back panel, a wipe-clean or waterproof lining, and detachable straps if you want to carry it more than one way. None of these are luxuries. They’re the difference between a bag and a chore.
The 6 styles that cover everything
1. Holdall
Sits between a suitcase and a backpack β which is why it’s also called a weekender. A staycation, an overnight flight to a European city, it handles all of it. Roomier than it looks, collapsible where it needs to be.
What to look for: a double zip, two hand straps, a detachable shoulder strap. Some have buttons on the sides β release them for more space, fasten them to keep it sleek when it’s not full.
Brands I’d shortlist: Bennett Winch, The Jacket Maker, Mulberry, Mismo, Brunello Cucinelli, Louis Vuitton, Troubadour, Carl Friedrik, Steele & Borough.
2. Tote
The tote is the smart-casual answer. In leather or nylon it’s sleek enough to replace a formal briefcase and casual enough for the gym β which makes it arguably the most versatile shape in this list.
One big compartment, open from the top. Zippered versions exist if security matters to you. And whatever you do, pick one with separate internal pockets, or you’ll be rummaging for your wallet at the worst possible moment.
Brands I’d shortlist: Want Les Essentiels, Mismo, Bennett Winch, Gucci, Porter-Yoshida & Co.
3. Backpack
The backpack is having a grown-up moment β hands-free, evenly balanced, and now coming out of serious designers rather than the school run. For a city commuter it’s the practical default.
What separates a good one: padded straps, a breathable channel against your back so you’re not sweating into it, a protected compartment for tech, and enough pockets that everything has a home.
Brands I’d shortlist: Steele & Borough, Maverick & Co., Master-Piece, Eastpak, Bennett Winch, Porter-Yoshida & Co., Herschel Supply Co., Sandqvist.
4. Briefcase
The old boxy rectangles are gone. The modern briefcase is curved, softer, streamlined β the banker connotation is mostly shed, and it’s now the cleanest way to carry a laptop into a serious room.
Look for solid but comfortable handles, a detachable shoulder strap for the days you can’t stand to carry it any longer, and a zip β with a lock, if you can get one. This is the one style where quality leather is non-negotiable.
Brands I’d shortlist: Dunhill, Aspinal of London, Carl Friedrik, Smythson, Bottega Veneta, Bennett Winch, Mismo, Maverick & Co.
5. Messenger
Smaller than a tote, worn across the body β the original commuter bag, and still the right answer for cyclists and anyone on a lot of movement. Long shoulder strap, a flap over the front (or a zip, for a more modern take).
It works best in hardwearing materials that take a beating: waxed or coated cotton, canvas, nylon. Adjustable, well-padded strap, and enough pockets to keep everyday essentials secure.
Brands I’d shortlist: Filson, Carl Friedrik, Aspinal of London, Barbour, Montblanc, Mismo, Blue de Chauffe.
6. Folio / pouch
If stealth is the goal, this is it. A well-sized portfolio or document holder fits a tablet or small laptop plus the papers for your next meeting. Zip for security, padding for the tech, and an internal divider so the device doesn’t live in the same space as the paperwork.
Leather here, without hesitation. It’s the briefcase’s quiet understudy β slip it under your arm and you’re done.
Brands I’d shortlist: Berluti, Tom Ford, Bennett Winch, Mismo, Common Projects, Comme des GarΓ§ons, Maverick & Co., Aspinal of London, Smythson.
The Edit
If you’re buying one bag this season, make it the tote or the holdall in a neutral you already wear. One shape, two jobs, zero decisions. Everything else you can earn later.
FAQ
A neutral-coloured tote or a small holdall. They cover work, weekend and travel in one purchase, and the neutral colour keeps them in rotation for years.What bag should I buy first?
Leather if the bag will see daily office use and you want it to age well. Canvas if it’s casual-first, budget-first, or going to get wet and rough. Coated canvas gives you the durability of the former at the price of the latter.Leather or canvas?
No. The list is a menu, not a shopping list. Most people need two: one for work, one for travel. Buy the work one first and make it good.Do I really need six bags?
a note from Margot
I spent ten years editing magazine racks. Now I edit your closet. And the truth about bags is the same as the truth about everything else in it: you don’t need the trend, you need the one thing that’s going to outlast it.
