Nothing says winter in Chicago quite like brightly colored polos and seersucker… OK maybe not, but hear me out. It’s actually not as crazy-over-the-top-preppy as I imagined it would be. For instance, on a day like today, who wouldn’t want to be home lounging in something like this?
Or I’m pretty sure I already own a version of this outfit:
Now sure, some items are over the top. For instance, I can’t imagine rocking this to the Christmas party (TBOX maybe!):
But I would absolutely done this little number under the mistletoe (too soon?):
I’ve never been to the Cape or the Hamptons or Martha’s Vineyard (that’s not to say I didn’t think twice about applying for this job), but I’m sure I’d love it. This is what I’d pack to go out there:
Because, you know, I’d be rich enough that whatever wouldn’t fit in this Weekender, I’d just buy there, duh : )