For travel I want three bags and no more: a tote that takes a laptop and goes under the seat, a crossbody small enough to wear through an airport with both hands free, and a weekender that fits two or three days without needing a wheel. Everything else is optional. The mistake I made for years was buying one large bag and expecting it to do all three jobs, which mostly meant carrying something half empty. Below, the totes, the crossbodies, and the weekenders and backpacks. The other thing I have learned is to keep the small bag inside the big one rather than carrying both. A crossbody that lives in the tote and comes out at the hotel is far more useful than one worn alongside it, which just means two straps competing for the same shoulder.

A travel tote lives or dies on whether it stands up when you put it down, and whether the opening closes. A structured base and a zip top are worth more than any amount of internal organisation. A zip top is the specification that matters most and the one most totes skip. An open tote on a train or in a queue is an invitation, and a magnetic snap is not a closure. Look for a flat base with feet, a strap long enough to clear a coat, and an internal sleeve for a laptop rather than a padded compartment, which mostly just adds weight.

Crossbody bags are the ones I care most about, because they are what I actually wear while moving. A strap you can shorten to sit at the hip and a flap that closes properly is the whole specification. This is the bag I care about most, because it is the one worn while moving. The strap should be adjustable enough to sit at the hip and wide enough not to cut, and the closure should be a zip or a proper flap rather than an open top. Anything under about two litres of volume becomes a phone and passport holder, which is a legitimate choice if the tote is doing the carrying.

Weekenders and backpacks are about volume against shape. A soft duffel packs into a case for the return leg; a structured one carries better on the shoulder. Both beat a small wheeled case for two nights. For two or three nights, a soft duffel beats a wheeled case on almost every measure except a long airport walk. Look for a strap that can be worn across the body, a base panel that is a separate piece of leather or coated canvas, and a shape that packs flat for the journey home. A backpack does the same job with better weight distribution and slightly less polish.

The Sak has been making soft, hand-woven bags for decades and they are the ones I reach for when the bag itself needs to survive being crammed under a seat. The totes and crossbodies are the strongest part of the range. The hand woven construction is the point: the bags soften rather than creasing, which suits a life spent being pushed under seats. Prices sit at a level where using a bag hard rather than protecting it is the obvious approach.

And the small things, the pouches and card holders that keep the inside of the bag from becoming a problem. The small things to finish, the pouches, card holders and wallets that stop the inside of a bag becoming the problem. One pouch for cables and one for documents is the whole system, and it removes most of the rummaging that makes travel tiring.

Pack the bag you are carrying, not the bag you own. I now check one thing before a trip: whether the shoulder strap sits comfortably with a coat on, because a strap that works over a t-shirt often does not clear a winter layer. And leave the expensive structured bag at home for travel. Airports are unkind to corners, and a bag that softens with wear ages far better than one that is meant to hold a line.