My Hunt for a Stylish Cross-body Bag That Won’t Stress My Arthritic Joints

Don’t get me wrong — I love the look and feel of this solid fall bag in plush brown suede. It’s a well-constructed, interestingly asymmetrical beauty that feels great to the touch. It’s roomier inside than it looks, which is a great feat of engineering. If I spotted another woman wearing it, I’d admire it and want it. The problem is it’s too heavy for my arthritis-riddled joints, even with none of my belongings tucked into it. This is a bag for someone who does not tell her husband upon waking just about every morning, “My entire skeleton hurts.” It’s also slightly out of my price range, even for my big birthday present.

I liked this bag because of its handsome, grown-up-professional look, which it has in spades. It’s lighter than it looks and very roomy. But the handles are far too big for my small frame. (I’m a hair under five feet.) The bag is nice-looking and high quality, but it overwhelms me. I imagine it would look better on someone taller.

This bag is classy, stylish, and well made, and I chose it for professional outings for which it might be useful to carry something that’s part handbag, part briefcase. But as much as I like the look of this, it is entirely too much bag for my small body. It’s also heavier than I’d imagined it would be, and given my orthopedic concerns, lighter is the only way to go. I envy the more statuesque nonarthritic women who can pull this off.

After the Oleg Cassini disco bag I carried to my bat mitzvah, the next pocketbook I owned, as a high-school freshman, was a shiny brown LeSportsac. It had a weird banana shape that I didn’t love, but I wanted the label — that brand was all the rage in my school in 1979 — so when I found one on clearance at Bloomingdale’s, I dropped all my babysitting money on it. I find LeSportsac to be enduringly chic, but what I like most about its bags is how light they are. This one is like a feather. I thought it might be good for when I fly and try to carry on both personal items and work things — reading material, my iPad mini, etc. But this bag is maybe too big and unstructured to look good on me.

Through this exercise, I might be discovering that the classic business-lady handbag-briefcase mash-up is not really my bag, so to speak. I mean, why do I need handles if I’m going to carry the bag across my body and not in my hands? But if I’m going to carry a handbag-briefcase mash-up to someplace where I need to look polished and professional, it will probably be this iteration. It’s much lighter than the others I’ve tried and not overwhelmingly large for my size, and the leather feels nice and soft. I also really love this color — I’m a freak for all shades of green.

[Editor’s note: This bag is currently out of stock.]

This is one of the smaller bags I chose for going out at night — the kind of evening when you need little more than your phone-wallet combo, a lipstick, and your keys. I love the classic look of this bag, its simple geometry, the feel of the matte black leather, and how deceivingly light it is. However, I didn’t realize just how slim a profile it has. It’s a tight squeeze fitting in just those three essential items. If only there were a little more space between the front and back.

[Editor’s note: This bag is currently out of stock.]

I aspire to be the kind of woman who can carry off a classic, sturdily constructed pocketbook with serious hardware like this one. But carrying it reminds me a bit of playing dress-up, like I’m trying to look more mature than I feel. Maybe I’d wear it on a more formal occasion. But it’s also on the heavy side, so I wouldn’t want to have it slung across my body for too long.

The leather on this bag is so incredibly soft and buttery. And the whole thing is so lightweight despite being roomy on the inside. I love the simple, straightforward style; the natural color; and the “broken-in” leather look and feel advertised in its name. It reminds me of the Il Bisonte bags some of the rich girls in college carried and I longed for. (I have an additional soft spot for Il Bisonte after the hit-and-run because that afternoon, before medics treated me, the woman behind the counter at the Il Bisonte store in Soho tended to me, giving me a bottle of water, cleaning up my scraped hands, dabbing my tears and streams of mascara off my cheeks.) But there’s something slightly awkward about the way the strap only attaches to the back of the bag and isn’t centered between the front and back. It makes the bag hang in an unbalanced way on me. It’s also on the pricey side for my budget.

Another big, slouchy black nylon bag. But this superlight quilted one feels more structured and cuter than the other. I can see bringing this on a plane as my carry-on bag and also tooling around whatever city I’ve landed in with it draped across me. Its weight is negligible, and it’s spacious enough that I can fill it with whatever I might need while I’m away from home. It’s also so affordable that, birthday or not, I can justify grabbing one in addition to a higher-ticket bag.

A bucket bag is a little dangerous for me. It’s so easy to just keep piling things in, eventually having little awareness of what’s at the bottom. In the late ’80s, one of my prized possessions was a chunky red Coach bucket bag with no compartments that an ex had bought me. Once when we were traveling, he offered to carry it for me because he saw I was struggling to lug it around. “What the hell do you have in here?” he asked. I dumped out its contents on the bed in our hotel room. In addition to a whole lot of other junk I didn’t need to be toting, there was a heavy stainless-steel set of lobster crackers from when we’d had a clambake months before. Am I now more capable of responsibly owning and operating this kind of bag? Of not turning into an overloaded catchall (for more than just prescription bottles of meloxicam)? I hope so because this suede one from Quince — with two small compartments — is lovely and light, and this is such a great fall color. I’d wear it on trips to the city, lately a mix of business and pleasure, for which I need to carry a bit more.

Speaking of Coach bags, this takes me to the opposite extreme from the heavy red bucket style I owned (and overloaded) in the late ’80s. This bag is the perfect size and weight for a going-out-at-night bag — roomier on the inside than it looks (but fortunately not big enough for me to accidentally stow metal kitchenware and tote it around for months on end). And the leather is lighter than on my earlier bag. It’s classic and classy without being fussy or too fancy, especially in this amber tone. And even though I don’t generally like visible labels, for some reason I’m not bothered by the tiny gilt insignia on the front. (I suppose I could also just turn it around.)

Early in my career I was a reporter–editor on the accessories beat at WWD. I remember receiving a sample of one of Bottega Veneta’s signature woven bags to write about and fell in love. Some day, I thought. At a fraction of the cost, this Madewell bag scratches that old itch. The leather is nice and soft and light in weight. This color is rich. And it’s a good size — a bit bigger than the average going-out-at-night bag and a bit more compact than your average everyday bag, meaning I won’t be tempted to pack it to the gills.

I’ve had my eye on so many Shinola bags (and watches and small leather goods) for a long time, so I’m glad I finally got the chance to try one. This is the perfect everyday saddle bag for me. It’s shaped a bit like a fanny pack but with a cross-body strap instead of an around-the-waist band. The back is flat, so it lies comfortably against your body. The leather is not heavy, and the size is just right. I’m really into this natural color, but I also like it in black.

The algorithm on just about every social-media platform has been showing me Portland Leather bags for years — especially this one. I have contemplated getting it, and for some reason, until now, I never did. I hate to admit it, but the algorithm was right. This is a perfect everyday bag for me. It’s the right size for carrying everything I need. Its shape is simple and neat. I love the color. And it’s not heavy at all. What’s more, the price is right— affordable enough that I’d consider getting it in one or more of the other nice shades, like cobalt or a green the brand calls bacalar.

It figures that I’d fall head over heels for the most expensive bag of the lot. After admiring friends’ bags from Lindquist Object — it’s kind of the “It”brand among some of my crowd — I was eager to try one out. They’re made of beautiful, sturdy leather but not too heavy. The styling is simple and classic. And this particular style has compartments for days — so many more than any of the other bags I’ve sampled. It’s a bit surprising to open a bag with this kind of fairly slim side profile and find that not only does it have three main compartments but also several smaller compartments and pockets inside the central one. That means having to carry fewer additional baglets inside my bag, thus lightening my load.