My travel broadly falls into three categories:
- <1 day trips. Meetings / study / shopping / eating
- Whole day trips. Work.
- 1+ day trips. Visiting my family. Vacations. Business trips.
I use a different bag for each purpose.
Small trips - Cambridge Satchel Company
I bought a Cambridge Satchel Co. Classical Satchel in the summer to replace a cheap shoulder bag which I'd been carrying since the early '00s, and was beginning to look like it'd been run over by a tank. I've loved the understated styling of the Cambridge Satchel Co. brand for years. It's smart and elegant; and I like that it transcends any social occasion. I could take it to a hipster cafe or a gig, but it doesn't look out of place at a pinstriped meeting either.
The leather is thick and a little inflexible although I expect it'll become more supple with age. Yet the bag is also relatively lightweight. I chose the 13-inch model. It's big enough for books, even my laptop in a pinch, but small enough that it forces me to be thoughtful about what I carry with me. This encourages me to empty it when I get home; processing any items I've collected throughout the day.
The satchel's discretion, plus the fact that it's not easy to open, makes me feel that I'll be less of a target for pickpockets, especially if I wear the bag across my body rather than dangling off a shoulder.
My one gripe is the strap. It's too thin and can dig into my shoulder, even through a thick coat and jumper when the bag is fully loaded. This can be addressed by buying a strap cushion which the bag a lot easier on your shoulder. It would be nice if Cambridge Satchel Co. would something like this with their bags but for a product I expect I'll be using for a decade, buying one myself is a relatively minor inconvenience.
Whole day trips
Trips which necessitate a change of clothes (like commuting to a day job with a dress code), or day-long expeditions, involve carrying more stuff. I prefer a backpack to a shoulder bag for anything this weighty.
The Berghaus Twentyfourseven 25L backpack is tough, discrete and inexpensive. As with the satchel, it works just as well when I wear shorts and a t-shirt as when I wear a suit. Most important, I find that it's comfortable with generously wide and soft straps.
>1 day trips
The inscrutably-named [Samsonite Base Hits 55cm Upright](http://www.samsonite.co.uk/base-hits-upright-55cm-20inch/59142.html?dwvar_59142_color=1598#start=3&cgid=SAMS6870) is the most effective roller bag I've tried. It feels tough, lightweight and perfectly sufficient for a week's travel (although I travel light). As with my other bags, discretion is the better part of valour. The wheels are relatively quiet even on rough pavements and the handle mechanism feels extremely robust.
The real trick to the way I organize my bags is that I keep a "pod" containing my entire suite of mobile tools. The ThisIsGround Mod has been a revelation. It's costly, but it's also something I expect to outlive me. The mod when closed has a clamshell form with a handle on one side and the kind of zipper that I'd normally expect to find on a parachute bag.
The inside front has loops for pens / stylii, and pockets for business cards, a smartphone or cables. The inside back has a large pocket for a tablet; and I manage to squeeze in my tablet's keyboard cover as well. The real trick is the insert. You can order your mod with one or more magnetically-attached inserts which are designed for different uses. I picked the Writer insert because I needed loops for extra pens, and a pocket for a pencil, eraser and sharpener. There's enough space behind the insert for a notebook as well.
The Mod has forced me to decide what I need to carry around with me at all times. Once that choice has been made, it's easy to transplant the Mod between the larger bags as needed; guaranteeing that I've always got my essentials with me.