I’ve not owned very many bags. As a guy in the US, I never was really expected to use a bag aside from the ubiquitous LLBean school backback. I always carried things in my pockets or chucked larger things in my car. When I lived in Rome in my early twenties I didn’t have a car and quickly realized I needed some kind of bag to carry all my stuff around in. Men carry bags in Italy, and there were lots of options. I bought a basic beige nylon messenger bag from Benetton. This was my first “nice” bag and I still own it. It toted my notebooks, pens, and supplies all over Rome while I took classes.
When I returned to the States and started working, I continued to carry this bag. By this point the bag was pretty dingy looking (mysteriously, the care label says only “do not wash”, with no further instructions for how to clean it). I was working as a community organizer at the time and my days often started at 8am and ended around 9pm. I ran from meeting to meeting all over the city and had a small and very messy office adjacent to a senior center. The Benetton bag easily toted my planner, notebook, address book, Nokia mobile phone, pens, and essential files. I carried keys, wallet, cigarettes, and lighter in trouser pockets.
When I changed jobs I actually went for several years without carrying any bag at all; I only needed a few things and they fit in my pockets. I eventually quit smoking which thinned down my “daily carry” necessities further. My work was largely predictable and I had very few appointments, so really had very little need of a planner
When my job suddenly became much more complicated, I started using a personal size Filofax and I realized I needed a bag again; I needed one immediately! I ordered something cheap from Amazon. It worked alright but looked and felt cheap.
I got this Jack Spade waxed canvas messenger bag for Christmas in 2012 and have carried it basically every day since. While it is not the perfect bag I must admit that it has served my needs very well indeed.
I try not to carry too much. I get around primarily on foot and so an umbrella is a necessity. This “Gust Buster” is just about the largest that will fit in this bag and is a decent brolly. I also own a full size Gust Buster and much prefer that one on a really rainy day but this red compact is good to have on hand.
I bought the navy blue pencil case from JetPens. It is really just the thing I needed to corral all the little things that get carried in my bag so they don’t all get lost in the bottom. I have various pens, replacement lead for my mechanical pencil, white rubber eraser, some decongestant tablets, chapstick, a small LED flashlight, my phone charger, a microfiber cleaning cloth for my eye glasses, and my checkbook in the main compartment. I keep some coins, bandaids, my phone headset, and a regular wooden pencil in the outer zip pocket. There is a set of Frixion highlighters in the flap pocket.
I have my BlackBerry Q10 phone in one of the bag pockets. I quite like this phone, I have a fine motor control impairment and strongly prefer the hardware keyboard; the new BlackBerry OS is modern and efficient.
I keep a Zebra F301 ballpoint pen in one of the pen slots. I find a ballpoint really practical to have on hand for checks, addressing envelopes, really anything which I want to be sure is totally waterproof.
I also keep this white Lamy Safari with an extra-fine nib. I keep this pen filled with Pilot blue ink which is quite waterproof and seems to work well on most paper. The Lamy is a decent, durable pen; I don’t worry much about losing it and it offers a very decent writing experience. I prefer a fountain pen for any extensive note-taking and for signing letters and documents but after years of angst I have given up on trying to find truly fountain-pen friendly planner paper for my Filofax.
My main complaint about this bag is that it is so unstructured that it ends up in a floppy mess whenever I take most of its contents out. It also is slightly too small to carry file folders and the lack of structure means that any documents carried need further protection to protect from bending and creasing. However, after two years of daily use it is really holding up very well for a cotton bag. It is very lightweight so is not bothersome to carry all day.