Carrying all of my stuff

Over the past month, I’ve had a few people ask me about bags. One particular person specifically remarked that it seemed like I had a different bag every single time I saw her.

In the interest of making it clear that I do not own dozens of bags, and also in a personal exercise to fully understand my own use of what bags I do own, here’s a quick rundown of the bags I’ve grown to love over the past decade.

Everyday Carry: Jack Spade Commuter Messenger

I don’t tend to take much with me when I’m out and about; depending on how long I’m leaving the house for, usually I make do with my wallet, phone, keys, and a small notebook shoved into my pockets. On days when I feel like I may need a few more things, or when I want my pockets to be less encumbered, I carry my Jack Spade messenger bag and I get incredibly happy.

The bag itself is simple and small, but it suits my needs perfectly: the padded pocket fits my 11’ MacBook Air, there are small pockets for my charging cables and lip balm, pen holders galore, enough room for my Panobook, and just enough space to cram anything else I may need in the few hours I am away.

Larger Everyday Carry: Line of Trade Briefcase

There are days when the usual everyday carry bag doesn’t quite cut it: my work-issued laptop doesn’t fit in the smaller bag, and when it’s cold, I need a place to toss a hat and gloves when I take them off. If I’m planning on doing some reading while I’m out, I carry a few books with me, too. On those days, I carry a small, hip, canvas briefcase that I got in a subscription box ages ago. I don’t subscribe to the box anymore, but the briefcase has remained part of my regular rotation.

Overnight Briefcase: Travelteq Original Briefcase

I’ll admit that I spent too much on this briefcase, but the amount of joy that it brings me—and the compliments I get on it every time I take out into public—really makes it worth the expense. The leather is soft and stunning; over the years, it has worn into a weathered, but classic, look. The interior is filled with all the pockets I need to carry a computer, cables, notebooks, and clothes for about two nights away. It’s simple, it’s elegant, it’s functional, but it still turns heads.

Workout Backpack: Aer Fit Pack

My wonderful wife often jokes that I have a Kickstarter problem; my response is that I just love supporting good people who have a dream to make great things. One of the projects I backed several years ago was the Aer Fit backpack, and it was a wonderful decision.

The backpack is perfect for days when I’m going to the gym, or heading out for outdoor activities. There’s a special pouch for my shoes and for my water bottle, an easily-accessible pouch for my change of clothes, , a bunch of dividers for my many notebooks and pens, and a padded section for the days when I need to take my laptop with me. Best of all, its incredibly comfortable to wear, and looks elegant and stylish even in an office setting.

Travel Carry-on: Jack Spade Wool Felt Duffle

This is the bag you’ll find me using in any trip that is more than a night or two. (I rarely travel with anything bigger than this, no matter what the length of the trip.) This is also the bag I get the most comments about: most people don’t see travel bags made with grey felt, and this one is impeccably made. It’s a bit of a statement bag, but it’s also extremely functional and packs a lot more than expected.

Finding it was serendipitous: I walked into the Jack Spade store in SoHo almost fifteen years ago, saw it sitting there on display, and was immediately smitten. They were out of stock, so I bought the store model off the shelf; I later found out that they had discontinued the model and wouldn’t have been able to order if I had waited instead of making an impulse purchase. It’s still one of my favorite purchases I’ve ever made.