One of the biggest challenges I have when traveling to a new destination is packing appropriately for daytime exploring. For better or worse, I'm not big on thinking in terms of being comfortable. For instance, I will only wear workout clothes and sneakers if I am truly working out, so that rules that look out!
After buying every flat known to man and in the process failing miserably in the comfort department, my prayers were finally answered by the fashion gods when I put my foot in a pair of Tod's loafers. These are literally the most comfortable flats ever and almost feel like I am wearing my favorite Restoration Hardware slippers (which I live in at home). While their price certainly make them an investment, these loafers are a classic wardrobe staple and will never go out of style. Even better yet, they come in so many fun colors! (I own white and orange, so far...)
Another good way to add chic to a comfortable outfit is through your accessories; for me, that's a headscarf, oversized sunglasses, big jewelry, and a red glossy lip.
You don't have to sacrifice fashion when being a tourist; you just need to think outside of the shoe box!
Red Headscarf: Similar
Sunglasses: Teggy French x Victory Optical
White Tassel Earrings: Lisi Lerch
Lipstick (Lady Danger)