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There’s prevailing wisdom in NYC that when someone tries to mug you that you should freely and without hesitation give your handbag over to your assailant. I’m pleased to report that in over a decade of living in the city, no one ever tried to mug me, thankfully because I do not subscribe to this belief. I would have eagerly given over my wallet or whatever other valuables they desired, but I would have fought to the death for any handbag in my collection.

My bags aren’t simply designer investments to me or the physical manifestation of an important milestone. They are also carefully acquired pieces that work well my body (size 26/28) and stature (I’m 6’2″). Not to mention that some sizes or colors were limited edition and are no longer available without relinquishing my retirement accounts and a kidney. Sure, we can order interchangeable straps on eBay, but it never has quite the same shine as the items that didn’t need to be modified.

It’s easy to believe that because handbags aren’t sized they should be able to be carried by everyone, but a crossbody style carried as a shoulder bag doesn’t have quite the same flair. When micrototes were au courant, I was afraid to carry one for fear of dwarfing it with my proportions.

The following list is in no way meant to be exhaustive. It’s merely based on my own experiences. If there’s a bag’s fit that surprised you or that you swear by, I’d love to hear about it the comments below.

2. Cambridge Satchel North South Tote

When I started working on this post, my beloved North South Tote was still on the Cambridge Satchel website, but as I write this, it’s seemingly no longer available. I hate to create any sense of FOMO, but you can still find previously loved versions on Poshmark & Depop.

My love for this bag, particularly because of my height, surprises me sometimes. It is made with Cambridge Satchel’s signature stuff leather, which works extremely well to keep this bag’s inverted wedge shape, even after years of rigorous use. The bottom of the bag is much stiffer than the top, making contents feels secure even though there is nothing to hold the bag closed.

The lack of top closure is one of the main selling points, in my opinion, as it is extremely easy to slide a tablet, notebook, or computer in and out quickly, making it ideal for hectic workdays, meetings, and conferences. The crossbody strap is long enough for me to wear with the puffiest of coats, and the shape keeps the bag close to the body, so I never felt exposed to theft on the NYC subway.

That being said, I wouldn’t recommend it for urban travel where you aren’t familiar with your surroundings. It’s fantastic for running errands, work, or road trips.

Cambridge Satchel North South Tote