Leggings are pretty much essential for me when flying, they are comfortable and warm and you can easily remove them once you arrive at your destination. In fact this entire outfit can be changed around for a super cute look when you get off the plane. Remove the cardigan and leggings, change out the flats for some gladiators and add some great jewelry and you have yourself a completely new look!
I splurged a little with the Cole Haan bag option, it's pricey but it's a timeless piece that will last for years. I also really like the other bag which is aptly named, the "voyage flight bag". Lucky for me, you can have two carry ons!