Honestly, although it will be most likely allowed, it really is not a "personal" item and it is inconsiderate to your other passengers. Why don't you just check one of the bags?
How is it inconsiderate?
You are adding stress to yourself; you said it in your very first post.
Everyone who has posted to date is in agreement here.
I am so sorry bavaria, I'm disagreeing.
First, to me, losing luggage (even though it only happens relatively rarely!) is far more stressful than carrying two bags on. I get to the airport early as a rule (which has been broke once or twice) and can easily juggle stuff between bags if needed, and have the time to check the size-checkers if I feel I am getting too close.
When on a carrier that allows two items, I use something official carry-on size or smaller, and then my personal item MUST be smaller than that. That's my rule.
Since ALL of our luggage is USA (and Europe last I checked) carryon size or smaller, that's easy to do!
I have NEVER had a problem fitting something under a seat, never.
On hubby's business trips, except for the Jazz plane in Canada and a puddle jumper in New Zealand (where our big, but still official carryon size, are too big for carrying on, same as Australia's rules), he carries a "Ful" brand multipocketed backpack stuffed with electronics, and he can fit those under seats no problem.
Now it's the handle that's worrisome. Do you have the exact, manufacturer-given, dimensions? Is it smaller than the official carryon size, when including the handle (I mean a closed handle of course)? You want to make sure it's small enough, and that the extras on the backpack aren't going to make it too big.
Since your stuff will fit into a tote, you could make it easier (In My Opinion...others I'm quite sure will disagree) on yourself and if the tote would be difficult in the airport, stick the tote in the backpack, and as you're at the gate waiting for the flight, move things from the backpack to the tote so that it's obviously a "purse".
I mean seriously, has anyone SEEN the enormous size of purses for the last 5 or so years? Those things are enormous! If an enormous Vera Bradley purse is allowed, a backpack that is small enough and carries the same items should be allowed, but if you're worried, just move them around from bag to bag. Stow the backpack in your overhead carryon, then once at the destination airport take a few moments to move it back to the more ergonomic bag.
Now all of this is contingent on you being OK to do it all...since you're taking drugs to deal with anxiety, you might not want to do any of this. Or you might want to get to the airport extra extra early, 3 hours or so, get yourself to the gate, do what you need, then take your pills. That's assuming you're traveling alone. I just know I wouldn't want to go through TSA while on something that might alter my brain and reactions.
that's a lot of talking, sorry!
Do you have any friends or family who travel often? Show them the backpack, get their opinion. See if they think it will stick out. The nice thing about DH's "Ful" backpack is that it's not *tall*, so it doesn't stick out. He does have a different backpack made by Targus that is tall (very ergonomic on the back) and can't go under the seats (we can tell just by looking).
And just a last tidbit! When I carry two things on, I make sure I'm *carrying* them. I pull nothing. I have to make SURE I can lift it. So I carry the items, one in front, one in back (if one thing has a strap I wear it crossbody and put the item either on the front or back of me, depending on where I need to carry the other thing). I get to my seat, pop in (helps to be 5'3"), put the smaller item on the seat with the bigger item in hand. I'm entirely out of the way of the aisle. As soon as there's a break in people coming through, I pop my upper body out, put my item in the overhead, and pop back in. Sit in my seat and get situated if I'm at the window, or just sit with other bag on my lap if there will be others coming by me. Once I can get situated fully, I take out whatever I might need, put it in the seatback pocket, then stuff my bag under the seat, put my seatbelt on, and I'm good to go with as little annoyance to others (unless they get annoyed that I'm makin' them look bad, my ego says in a funny voice, LOL) as is humanly possible!
Good luck!!!!
