The honest answer to which everyday bag holds up is that it depends on what you put in it and where you put the bag down. Nylon wins on weight and weather. It shrugs off rain, wipes clean, and a packable tote weighs almost nothing when empty, which matters when the bag itself is already a pound before you add a laptop. Leather wins on structure and age. It holds a shape, it takes a scuff and turns it into patina, and a well made leather bag is usually still in service when a nylon one has worn through at the corners. Canvas sits between the two, cheap to replace and pleasant to carry, but it stains and it sags. Before you shop, empty your current bag onto a table. If the pile includes a laptop, a water bottle and a pair of shoes, you need a structured base and a wide strap. If it is a phone, keys and a card case, almost anything works and you should buy for looks.

Straps fail first. A thin strap on a heavy bag digs in and eventually tears at the anchor point, so check how the strap attaches: stitched-and-riveted lasts, glued does not. Look at the base. Feet on the bottom keep the underside off pavement and are the single cheapest thing a maker can do to extend a bag's life. Zips are the other common failure, and a chunky metal zip pull outlives a small nylon one by years. On leather, full grain and vegetable tanned age best; corrected grain with a heavy coating looks perfect in the shop and cracks later. Check the lining too, because a shredded lining makes a good bag unusable long before the outside gives up. Finally, weigh it. Anything over about two pounds empty is a bag you will stop carrying by November, whatever it cost.

Most people need three: one small bag for evenings and errands, one structured mid-size for work, one soft large one for travel and overflow. Buy the mid-size first and buy it in a colour you will not tire of, because it does the most work. The small bag is where you can be playful, since it carries almost nothing and takes almost no abuse. For the large one, choose packable nylon rather than leather, because you will be shoving it under a seat. If you commute, keep the work bag's contents in a pouch so you can lift the whole set into the weekend bag without repacking. Clean leather twice a year with a damp cloth and a conditioner, and let a wet bag dry away from a radiator, because heat is what cracks it. Store bags upright with something soft inside so they keep their shape.

Buy fewer bags and carry them harder. The structured mid-size is the only one worth spending real money on, because it is the one that gets opened five times a day and judged in a meeting. Do not buy a heavy leather tote if you already know you carry a laptop, a lunch and a gym kit, and do not buy a delicate suede anything if you live somewhere it rains sideways. Skip the tiny bag that fits nothing unless you genuinely want the object rather than the utility. If you take one thing away: pick up the empty bag before you buy it, and if it already feels heavy in your hand, it will feel unbearable at the end of a Tuesday.