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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.


1. 3.1 Phillip Lim Pashli in Medium

From the moment I saw the fuchsia color of the Phillip Lim Pashli arrive on Shopbop, I knew that it had to be mine. At the time, Shopbop was paying me in gift cards to run a widget in my blog sidebar, so I saved them month after month and patiently waited for a sale, anxious that the color might sell out.  Once I had enough banked, I ordered it shipped overnight and immediately tore open the box with my bare hands when it arrived. I was excited, to say the least.

I never anticipated the Pashli to be my most worn bag, but because of its versatility, I find myself reaching for it for both fashion & utility. My Surface Pro fits into it perfectly and the zippers in the front allow it to expand while still maintaining the shape and stability. The leather it’s crafted from is thick and substantial, so I haven’t had to worry about scratches, dirt, or rain.

Like most designer handbags, the price has increased over the years, but I would still highly recommend the Pashli for anyone who has even a passing interest in owning it after all this time. Fortunately, this color and size are still available from Phillip Lim if you want to be bag twins with me and Miss Whoever You Are.

Phillip Lim Pashli Crossbody