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The Search for the Perfect Bag

Writer's picture: Danielle DavisRoeDanielle DavisRoe

Previously, I shared my favorite carry-on bag. This week, I want to share my struggles with finding the perfect laptop bag (also known to airlines as a "personal item"). I typically travel with both my 14” laptop and a 12.9” iPad Pro. I want to get to the point where I only need my iPad on the road, but right now, that’s just not feasible. Along with my larger electronics, I carry my laptop’s power brick, a 4-port USB wall charger, 4 USB charging cables, USB-C to USB-A converters, USB-A to USB-C converters, a mouse, a pointer, USB thumbsticks, and a few other converters.


The trick is keeping all of this organized in a professional-looking bag that offers the flexibility to throw in the occasional airport impulse purchase (I suffer from guilty mom syndrome), a sweater, or even my winter coat while I’m in transit. My desire to stuff a sweater or winter coat in my bag rules out a traditional laptop bag - they don't include a large enough compartment. My desire to look professional rules out more practical backpacks that look like they are designed for the trail. (I have those; I love them; I keep them for use in the great outdoors.)

Right now, the best solution I have is a large leather tote bag, the Women's Lifetime Leather Tote Bag from the Duluth Trading company. I love how it doesn’t look like a traditional laptop bag. With its thick, full-grain leather, it has developed a beautiful patina from all of its bumps and scratches. It has one large interior compartment that zips closed so that I don’t have to worry about anything falling out. It has two smaller compartments about the size of a water bottle. These are great for throwing my phone in while I’m on the go - providing easy access when needed. These compartments are slim enough that I don’t worry about my phone falling out as long as the bag is more-or-less upright.


My only struggle with it is organization. Inside the main zippered compartment, there are two smaller compartments, just big enough for a container of mints, a lipstick, and some business cards. There are no cord organizers or convenient ways to organize thumb drive and converters. That’s where cord organizers come in. Sometimes, I feel like I’ve tried them all, even though I know I’ve barely scratched the surface of the thousands (if not millions) of options out there.


Most of the organizers are padded, which adds a decent amount of bulk if you aren’t storing anything that needs protection. Many of them are too compact to hold everything. The ones that fit everything are thick. My bag is large, but it doesn’t have a lot of space for anything thick. I'm continually searching for better organizers, but right now, a small bag that holds my converters and flash drives and band-covered board that holds the cords and bulkier items are doing the trick.


Do you have a bag or organizer that you love? I’d love to hear from you. Please share in the comments below, connect with me on LinkedIn, or Contact Me.

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