Originally published in the November-December 2019 issue of Caribbean Beat.

A bag, I’ve come to believe, should have a shape that conforms to your travelling needs.

Most travel luggage is pretty straightforward. They are shells that offer varying levels of protection, a few pockets to organise the interior, but it’s just a hollow box for your stuff.

It’s also what leaves you at the checkout counter. With an decreasing amount of space available for carry-ons, I need to make the gear I can’t do without fit shrinking restrictions.

That’s led to reductions in the size of the devices I travel with, but there are things I absolutely need as a writer and photographer, and my shoulder bag remains the focus of my thinking whenever a trip gets booked.

On my first professional travel assignment for computer journalism reporting in 2005, I crammed a laptop sleeve into the backpocket of a photographer’s bag and hooked everything together with carabiners.

It was hideous, but it protected camera gear and a laptop with space for all the peripherals I’m yoked to for working remotely. It was also readily accessible for TSA searches and for disgorging equipment for separate scanning.

Business trips often require multiple transfers and sometimes jogs through an airport terminal to catch a connecting flight. Checked baggage is always more prone to tardy arrival or complete disappearance on such jaunts, so I try to keep everything with me.

A small roller and a shoulder bag work well for my personal travel profile, but everything has to fit, even on smaller aircraft. I can work without fresh underwear, but I’m helpless without my devices, so the roller can go in the hold but I need the shoulder bag, thank you.

Since then, I’ve worked with three bags seeking the best possible bit of hand luggage. The first, a hefty marriage of camera and laptop bag from Tenba, eventually fell afoul of reduced dimensions for carry-ons.

It’s successor didn’t have a properly designed computer compartment and offered too little protection for my taste, though it had the right shape.

I’m partial to shoulder bags, but there are a many backpack style bags in a range of sizes that are also suitable, so people with similar gear needs might find those appropriate.

My travels began with a small DSLR kit, a 15-inch laptop, and all the chargers and transfer cables associated with making everything work.

I’ve since scaled down to a prosumer point and shoot, the Canon G1X (currently in a Mark III edition) and the laptop is a thinner, lighter model.

The current bag is the Urban Disguise 60 (currently out of production) which ThinkTank ships with sensible pockets and a truly crazy number of separators. These are critical to keeping gear organised and accessible. The bag isn’t just for travel; it’s also a workspace once I arrive.

“…when it comes to travel, form should follow function”

Now, I should admit that I’m a bit of a bag addict when it comes to gear containers, and I haven’t stopped looking for the next great one, but when it comes to travel, form should follow function.

A carry-on shoulder bag should attach firmly to the extensible handle of your roller. There’s nothing more appalling than having to stop a desperate run for a closing flight to adjust a bag that’s swinging wildly.

Any travel bag should be anonymous, perhaps even a bit ugly. Bags that advertise expensive contents should be avoided at all costs and while a carry-on should never leave your side, it shouldn’t make you a target.

Eventually, it will have to sit on your shoulder, so confirm it has a strong, comfortable strap (same goes for backpacks).

A truly great carry-on disappears. It fits where it needs to go. Pleases checkout counter clerks and safety inspectors and most critically, keeps your gear with you, ready for action.

What’s in the photo?

Clockwise from top left: Urban Disguise 60 bag; toiletries bag; external battery and cables bag; DSLR camera and lenses (usually just the G1X); noise-cancelling over-ear headphones; foldable laptop cooling bar (must have for image and video editing sessions); iPad with one charger each for laptop and mobile devices; MacBook Pro; prescription reading glasses and my travel documents wallet.