Choosing a work bag: briefcase, messenger or tote?

The right work bag depends less on style than on three practical questions: what you carry, how you travel, and how formal your days are. Answer those and the choice between a briefcase, a messenger and a tote tends to make itself.

Start with what goes inside

Measure the laptop, not the sleeve it came in. Most 13–14 inch machines need an interior of at least 33 × 23 cm; a 16 inch needs 36 × 25 cm. Add a charger, a notebook, a water bottle and, honestly, a jumper, and you have a volume. A bag that is “almost big enough” is the one you stop using.

The briefcase

Structured, flap or frame closure, carried by a top handle with a detachable shoulder strap. It protects a laptop best, keeps documents flat and reads as formal. Choose it if your week is meetings, client visits and a car or taxi between them. The trade-offs: weight (structure means more leather and a reinforced base), and it is awkward on a bicycle or a crowded train.

The messenger

Softer, worn across the body, usually with a flap and a quick-release buckle. It is the most comfortable option for walking, cycling and commuting by train, and it looks right with knitwear and a coat as well as a jacket. It is less protective of a laptop — look for a padded sleeve — and less formal; in a very traditional office it can read as casual.

The tote

Open or zipped, carried on the shoulder, with the most capacity per gram of leather. It swallows a laptop, files, gym kit and a lunch, and moves from office to evening without looking like luggage. It offers the least organisation unless it has a fitted interior, and an open top is not ideal in heavy rain or on a packed Underground.

Three details worth paying for

• Feet or a reinforced base. A work bag spends a lot of its life on floors.
• A strap that detaches and adjusts. You will carry it differently in July and in January.
• A lining you can see into. A light cotton lining makes a black bag usable; a black-on-black interior is where keys go to disappear.

Our shortlist

For a formal week, the Executive Brown Briefcase or the Pacific Leather Briefcase. For commuting, a messenger from the men’s range. For an office that is also a studio, a structured tote from the women’s range — several are cut with a full-length laptop pocket. And whichever you choose, we will press your initials into it before it leaves.