BUT I'm happy to say that with careful planning, I managed to squeeze several mix-and-match outfits in my little suitcase and duffle. These aren't the exact clothes I packed, but they're very close approximations.
I packed a bunch of neutrals that can be mixed and matched to create about 11 outfits. It's good to mix in some patterns to spice it up a little, but if they're neutral patterns, you still have a lot to work with. For shoes, I went with a couple pairs of flats, Sperrys and boots.
The key to making all that fit is to roll each item up, and put some of the most essential basics in your carry-on so you aren't totally lost if your luggage never makes it. The boots I packed can fold down, and I put my other shoes in the front storage compartment on my suitcase. I like to look nice on vacay, partially because it's one of the only times in life you're ever really focused on taking lots of pictures, and also because I'm old school and I like dressing up for travel. Just once, I want to look like this when I get off the plane or train: