The context

There is this great line in the movie When Harry Met Sally about classifying women (or men, for that matter). There are three types. First is the high-maintenance type and we all know who they are. Second is the low-maintenance laid-back easy-going type. The third is the trickiest. As Harry says, this is a “high-maintenance (woman) who thinks she is a low-maintenance (woman)”.

The same could be said with men and travel. You think that it is the dads who are easy-going with respect to vacations. And maybe they are. But when it comes to business travel, it is a whole new world.

Men are more finicky than women when it comes to business luggage. Or perhaps it is a toss. Perhaps because they travel more often, men have very fixed views on say, what constitutes good briefs—or for that matter, a good briefcase. It has to have two large flaps, plus enough pockets for devices, plus a pullout keyring so you ain’t fishing for house keys at midnight. Just writing down this list of requirements is enough to make a designer exhausted.

Packing for a business trip isn’t rocket science. Heck, it isn’t even as crazy as planning a menu for dinner guests who are vegan or won’t eat shellfish or want free-range beef from happy holy cows. But somehow, men get strangely finicky and inflexible when it comes to overnight business trips. Everything has to be just so. Why?

The fantasy

For a married man, however happily so, the realms of control are shrinking. The irony is that he doesn’t realize it. So he seeks areas where he has a semblance of command. Packing for a business trip is one. Nobody—not spouse, not children—can interfere, not that they’d want to. It is almost as if the poor married sod wants to tick off every quality that his wife and life lacks, and control for every variable—things that he cannot do at home. What he has ceded as erstwhile master of the universe, he recaptures with business luggage. It is like a full-blown identity crisis.

The problem begins with job title and description. Are you a leather-goods kinda guy, or are you the laid-back Silicon Valley T-shirt and backpack kinda guy? This briefcase, or more aptly, backpack, is for the latter.

The reality

Today’s trips are a one-night stand or stopover. You go for a day or two to multiple locations. The question is which luggage will work. Choosing the right piece of luggage for your business trips is like choosing a date. It depends on not just what they are like, but also what you are like (or what you think you are like).

Are you a rugged individualist who carries backpacks rigged with straps for equipment? Or are you a sleek, dapper dude? Are you someone who likes all options open? If so, Eagle Creek’s Convertabrief is for you.

The product

How many times have you gone on a business trip with an extra handbag or backpack for local forays—either to shop or visit a museum, should you be culturally inclined? How many times have you forgotten said extra backpack?

The Eagle Creek DoubleBack carry-on is, as its name indicates, a double backpack. The smaller daypack clips on to its mother—the bigger backpack with wheels— like a kangaroo cub or joey sits on its mother’s chest. Earlier designs had the daypack zipped to the mother, which was helpful for arthritic fingers, but tough on zippers.

The base is a large backpack with wheels. Lest you wonder why anyone who has a wheelie would want to carry a backpack, let me point you back to the male business traveller and the number of boxes that he wants to check in. The backpack is useful not just to sprint through terminals when you are late for a flight, but also to appear casual and cool while walking into business conferences. The “suits” carry leather briefcases. The cool dudes carry a backpack.

The backpack comes with two wheels and is not a spinner. It has one retractable handle, which seems like too little for the amount that it purports to carry. A normal two-handle model would have been sturdier.

Inside the backpack is empty space. Outside is where the drama is at. There is a “daisy chain” not to secure daisy flowers but to hook rock-climbing or trekking gear in case you decide to hit the Himalayas after your meeting in Delhi. There are compression straps to remove the air out of clothes. There are reflectors in case you decide to trek at night. This is, in other words, a adventurous person’s backpack.

The Convertabrief is beautifully designed. No two ways about it. Having explored Tumi, Samsonite, Victorinox and many other brands, I have to admit that this brief ticks off many boxes. For one thing, it has a fold in the back which means that you can slide it over rolling carry-ons. It slides awkwardly over the Doubleback.

The second is that it converts into a backpack, cross-body messenger bag, handbag and over-the-wheelie briefcase. It has two flaps: one for the computer and another for the iPad or tablet device. You unzip this compartment and can place as is through the security belt. There is a front flap for documents and all those little pockets for passports, tickets, headphones, pens and the usual accoutrements.

Fitting all this takes up space and that is the problem. The Convertabrief is big. It works for overnight travel where you want to throw in a shirt and trouser, but if you are going just for the day to Bombay or Delhi, you will find this too capacious for your needs.

The second problem is more universal. When luggage manufacturers put in so many pockets, they really need to label them. Half the time, you are staring at the pockets wondering what to put in there. Then you have to memorize what you put where. It is the opposite of a no-brainer. Labels saying “keys” or “headphones” would help.

The details

The DoubleBack Carry-On and the Convertabrief are available from Eagle Creek.

Convertabrief ($199)

DoubleBack Carry-On (299)

The verdict

If you are going on an overnight trip, the Convertabrief is a good choice. If you are travelling over a continent for a week, the Doublebag is a great choice. Neither has the style and sexiness of an Italian brand.