Finding a bag that can pass for your personal item on the plane while holding a laptop, notebooks, files and all of the modern traveler’s accessories is a real pain. That pain is amplified when said bag needs to also pass for a business bag at whatever event or meeting you’re traveling to.

My personal struggle looked something like this:

Backpacks are great, and my company even provided me with a branded Ogio backpack. But I couldn’t bring myself to rock a techy backpack with my chic sheath dresses, tailored blazers and heels. Plus, it is HUGE, so my overpacking ways led to it barely fitting under the seat in front of me. Double fail. I have a fabulous Coach messenger bag that serves me well day-to-day, but it wasn’t a great travel bag. Once I loaded in my laptop, notebook and files for the trip, there was barely any room for the extras that I usually travel with (iPad, noise canceling headphones, pens, camera, chargers for all of my electronics, etc).

Short of lugging a small duffel/backpack and PACKING my business bag (which I have resorted to in the past), I was out of options and needed to find something that could be my all-in-one personal item/business bag.

It was a chance encounter in the Grand Rapids, MI airport that led me to discover the first real contender. A lady with good style sat down across from me at the gate. My eyes immediately went to the big (but not too big) black tote sitting at her feet.

The bag looked perfect, so I tried to indiscreetly look for the brand name so I could search for it online, but I couldn’t find one. Not wanting the moment to pass me by, I pinged her with 20 questions about her bag. It was a Lole Lily Tote Bag.

She was in LOVE with her tote and gushed about it. I wasn’t completely sold after our conversation (the material was a little flimsy), but I knew it was better than most of what I had found so far. So as soon as we got above 10K feet, I popped open my laptop and ordered one online.

While I waited for that one to be delivered, I found one other contender at Nordstrom’s: the Marc Jacobs Pretty Nylon Eliz-A-Baby Diaper Bag. (Sidenote: some of my best bags have been baby bags; I own three, despite not having an actual baby.) The Eliz-A-Baby was huge, had lots of pockets, and at least two ways to carry it.

I bought it and waited for my Lole to be delivered. These two bags then battled it out for my ultimate love.

Stop by tomorrow to find out which one won it’s rightful place by my side. (pun intended)