I’m going out of town soon, and while I eventually may be more concerned about how I look without clothes, figuring out what to pack is always a challenge—particularly when you’re leaving someplace frigid for someplace with (hopefully) more temperate weather. And of course there’s the issue of designing an outfit around easy-to-remove footwear for the flights. And making sure sure everything fits into a carry-on.

The key, of course, is to have everything work together. For me, that means going classic—a lot of neutrals, with color and personal style provided by accessories—because if you’re going all Lady Gaga, you better make sure you have the entourage to carry your luggage for you.