Men tend to replace a work bag only when the old one fails, which makes it both the best and the riskiest gift. Best, because the upgrade is genuinely felt every day. Riskiest, because if the size is wrong it goes in a cupboard.

Start with the laptop

Everything follows from the machine he carries. A 13 or 14 inch needs the small briefcase; a 15 or 16 inch needs the large, and the small one will not take it. If you do not know, check the box or the settings screen, or buy a duffle instead, where sizing is far more forgiving.

Briefcase, messenger or backpack

If he walks or cycles any real distance, a messenger or a backpack will get used and a briefcase will not. If he drives and walks from a car park into meetings, a briefcase is the better looking and perfectly practical choice.

The safe small gifts

A toiletry bag is the accessory men use most and buy for themselves least, which is what makes it a good gift. A watch roll if he has watches. A cable case if he travels for work. All take a monogram free.

Hardware

Brass reads traditional and warms with age. Gunmetal and black hardware read modern and stay as they are. Both are on the product pages, so you can match whatever he already wears.