Going bold is always something we should all strive to do. Pushing out of your comfort zone, even just when it comes to getting dressed, almost always pays off. If you’re squeamish about getting a little too adventurous with your outfit, look to an out-there bag with brash graphics. Wearing a standout bag is much easier for more timid snobs to handle, since there’s more of a physical disconnect (read: you’re not say, zipped into it).