I have a bag that I lovelovelove.

What you see above is a vintage Samsonite carry-on flight bag in blue leather. Amazing, yes?

I’ve had it for two years, and I’ve carried it across the country, on numerous plane trips, and on the subway every day. I bought it for $20 at a thrift store in Bloomington, Indiana, and it’s held up excellently—I had my tailor fix the broken zipper on it about three months ago, but besides that, it’s been my go-to for hauling all the junk I need around the city every day.

I love it because it’s stylish and chic. I love it because I’ve never had the experience of seeing someone carrying my exact identical bag. I love it because it’s got enough pockets to keep my things neat, but not too many pockets (which would encourage me to drag way too much stuff with me). I love it because it’s waterproof (remember what happened with my former favorite white leather bag in the rain? it’s not going to happen with this one…). I love it because it’s durable. I love it because it’s large enough to carry my MacBook, my journal, an extra sweater, and the heels that I’m going to wear to work (because, you know, I never commute in my good heels).

Before this bag, I’d gone through a number of unsatisfactory ones. I carried an Old Navy messenger throughout most of college, and that held up nicely, but it had no small pockets, so all my pens would get lost in my books, I impulse-bought a tote bag from my work, and while it was large enough to carry all my stuff, it didn’t close at the top, so I was always afraid of losing something on the subway. My stylish white faux-leather bag from Forever 21 last summer, which I loved, fell apart in about a month and a half and also got my stuff all wet. (Yes, I’m still bitter. Very bitter.)

Among my friends, my plight of searching for a decent bag is no new thing. Last year Katherine had a hell of a time finding a bag that was big enough to carry architectural drafting tools and large-scale drawings. Lori wanted a bag that was secure from theft for traveling in Europe. And both Daniel and Robert carry messengers that have fallen apart in the past couple of years. It seems like everyone is unsatisfied with the bags they have and use, and hence is shopping for something that they like better.

The shopping process seems like it should be obvious—you should buy what you like, right? However, it’s way too easy to start shopping casually for a bag without identifying what you actually need. Before you know it, you’ll end up bringing home four new totes—two that fall apart after two weeks’ use each, one whose strap makes your shoulder dislocate every time you hold it for more than three minutes at a time, and one that doesn’t come close to holding everything that you need before noon. So think about it. Below are some things you should ask yourself before buying a bag.

  • What kind of bag do you need? What do you carry every day? How much stress do you put on your bags? Do you prefer carrying everything in one large bag, or do you like having a small work bag, a small gym bag, a small purse, and a small laptop case? How far do you have to go with your bag—a quick trip in your car, or an hour’s commute via public transit? What’s the climate in your area, and how much exposure to the elements will your bag have?
  • Why do you need a bag? What do you love (or hate) about the bag you already have? Is there anything not working? What features could make it work better—padded straps, waterproof materials, a padded separate compartment for laptops?
  • What styles and fabrics would go with your personal style? What’s your personal clothing style, and what kinds of bags would go with it? (Or, if your doesn’t match what you might be wearing on any given day, do you care?) Do you wear leather? Do you like lots of hardware on your bags, or would it just catch on your clothing and annoy you?
  • What kind of bags does your body like (or dislike)carrying? Have you ever injured your back or shoulders? Do you get sore from lifting your bag? What kind of sustained lifting do you do every day—do you carry your bag for a few minutes at a time, or an hour or more at a time? How coordinated are you—do you trip and fall often enough that carrying something heavy could be a hazard for you?
  • How well do you care for your clothing—and will you put in the time to keep your bag looking great? Do you own (and use) leather polish? Do you know how to fix torn interior seams, broken grommets, or stuck zippers—and do you actually do it? Or, barring this, do you have a tailor or a cobbler that you can trust to do decent repair work?
  • How much can you afford? Have you been saving for a new bag? Can you afford a handful of really great quality bags, or just one (because, you know, the cost per wear is way lower when you buy better quality)?

    • Stylish readers: What kind of bag do you carry? How do you like it? What do you look for a in a great bag?

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  1. In My Bag: 10.30.08