They always fit :)
I also am a big bag kind of girl. I carry around a lot of stuff (useless or not), AND I have a theory...the bigger the bag, the skinnier you look!
I love the below two....classic, sporty, and never going out of style.
#1 lust....Barbour Bedale Business Bag. LOVE. 50% off at Aaron's of Eastham, a GREAT Barbour destination.
#2 Filson Carry All - I saw this bag at an industry event when it was not made yet. It is fabulous. Classic filson color and leather, updated style. It is big...a tote for some, a purse for me....we have them coming to the store in just a week or two. Stay tuned for pics. (admittedly, I love Filson. I have the open topped tote, shown below, and use it all the time)