There are days in life when you just need to be comfortable, but your elastic-waist college sweatpants (sadly) just won't do: long flights, running errands during daylight hours, or watching college football in public. This tee and jeans are so soft but polished enough that you won't be embarrassed to be seen by others. Bonus points for a pretty cross-body (code for hands-free) bag, comfortable rubber-soled flats, a sturdy watch, and a cozy scarf.
J. Crew Cece leather flats, $138.
Coach Legacy Colorblock Leather Patricia, $398 (a splurge -- but hey, if you take care of it, perhaps it'll end up your granddaughter's one day! I have a Coach bag of my grandma's that makes me happy every time I use it).