Ladies... carry-on that doubles as hand bag... any suggestions

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My OMG has arrived, trying it out as my everyday bag just at the moment.
2 things come to mind - the top opening is not very wide, and if you use the "shoe" compartment, you to loose a fair amount of space inside the main compartment. But my Ipad Pro 12.5 fits beautifully, will see how my laptop goes later today.

I have a love/hate relationship with this bag. I am currently in hate stage for what you stated, the opening is not very big. BUT I love that it has a solid pocket for my laptop. But after 3 years of hard travel, the corners are starting to wear, so I am "shopping" for the elusive perfect bag. I need something just a bit bigger but with the same functionality
 
Not sure I will keep OMG as an everyday bag for following reasons:
Pics below - I will have to cut off the hanging tag, it keeps falling into the zipper compartment. Can't remove and put on other side.
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Just found out my Ipad and laptop are the same size.... so both fit very nicely.

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Another issue is when you use the "shoes" compartment, it becomes difficult to find your loose items in the main compartment.

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Being a "short ase" 5'4" I feel the bag is just too close to the ground when being held by the handles. (wish they were adjustable).
I do think this bag will be fine as a "holiday/carry-on hand bag, only because I would use the outside zip section more than anything else for my travel wallet, phone, passport etc, with the main compartment for camera/books, and Missy can travel safe & secure in she shoe compartment, without having my bag open.

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So in my opinion, the OMG will be fine to take on holidays, think I will go back to my old everyday work bag.
 
So... I've ripped a hole in my OG. I realized this as I was heading out for 2 week trip. No problem, I had an older Tumi that was in service before. And as I am at the the airport, I remembered why it went out of service.

I need something big enough for laptop, and junk that I "must" have on planes. The ideal bag would have any opening big enough to stuff my actually purse inside as well. I know I am looking for a bag for my bag. Which has lead me my next problem, finding a new travel purse. Smaller bag for traveling, but big enough for an umbrella, wallet, water bottle.

I think I just to find someone to design the perfect bag for me. Anyone what to have some fun????

P.S. From my previous post, I did end up buying a ladybug umbrella
 
I posed this question to MrsQS:

“Why do you need a handbag plus a carry on on such a short flight?. “

I never got an verbal answer. Just a “look”
 
I sometimes look at people, walking around the terminal with nothing but a boarding pass and wonder how freeing it would be, to travel so simply.

But then Im reminded I have my husband with me, who packs the kitchen sink.
 
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