I’m planning a trip to Florence, and since shoes are the hardest things to pack, I’m already strategizing a game plan (sounds silly until you have even one bad experience – you don’t want to end up suffering in silence or complaining the ears off your travel companions). You need the right shoe for every occasion but you also must consider comfort, packability, and site-seeing ready – it’s a lot to consider! Here are my travel essentials:

Jimmy Choo Frosting Suede Slingbacks: Nothing beats Choo wedges when it comes to comfort. I have this exact pair in plenty of iterations (snake, suede, espadrilles), but for travel this nude offers the ultimate in versatility – suede means no blisters and the gold trim will still get you to cocktail parties with pizzazz. On Net-a-Porter for $775.

Play Comme de Garçons for Converse: I can tell you that wedges are comfortable, and for a shoe with some height, they are. But nothing beats a sneaker! At J. Crew for $100.

Lanvin Wedge Ankle Boot: Tried and true, these are like sneakers in boot form. Wear them with any pant and if done right, even with dresses. I really love these – they won’t wow the crowd, but you won’t care when you’re having a good time, instead of cringing with every step. At Barneys New York for $850.

Bloch Two-Tone Canvas Ballet Flats: You need a pair of the ever-ubiquitous ballet flats in your bag at all times. These are small enough to fit in your mid-size clutch for when the party reveling gets out of hand (last year in Florence I fell on the cobblestone street and woke up with a swollen ankle, so I’ll be getting these as insurance). On Net-a-Porter for $130.

Tabitha Simmons Flossie Printed Silk Sandal: I really don’t believe in packing more than 4 pairs of shoes, but since you’ll be wearing one your feet and the ballet flats are like nothing at all, I can consider a 5th pair! If you’re planning on doing something festive where you’re going, you’ll need some fun, flirty shoes. These are done in multiple hues, ensuring that they’ll go with whatever you pick up shopping. At Bergdorf Goodman for $547 (from $1,095).