The fastest way to ruin a week in Rome, Lisbon or Prague is the wrong shoes. Old European cities are built on cobblestones, hills and stairs, and most visitors walk far more than they do at home. The good news is that the shoes that work best also happen to look the most at home in those cities.

What Makes a Good City Shoe

• A cushioned, flexible sole that absorbs uneven stone.
• A low, stable heel, or none at all. Narrow heels catch between cobbles.
• Leather or suede uppers that look polished at dinner.
• A secure fit at the heel so your foot does not slide.

The Shoes to Pack

Loafers with a rubber or cushioned sole go from museum to restaurant. Leather sneakers in white, cream or black are accepted almost everywhere in the day. Low ankle boots with a block heel or lug sole are the autumn workhorse, warm and rain-proof enough for most weather. For evening, a block-heel or a sleek flat is more practical than a stiletto.

Break Them In

Never take new shoes on a walking trip. Wear them for at least a week of normal days before you leave, and pack blister bandages anyway.

Lisbon and Other Slippery Cities

Some cities are paved with polished limestone that becomes slick when wet; Lisbon is the classic example. Choose a sole with real grip, and save smooth leather soles for dry days.

The Two-Pair Rule

Bring two pairs you can walk in all day and alternate them. Shoes last longer and feet suffer less when neither pair is worn two days running.

Shop the Edit

• Tod’s Gommino Suede Loafer in Tabacco, Saks Fifth Avenue
• Common Projects Achilles Low Sneaker, FWRD
• Aquatalia Natta Suede Ankle Boot, Aquatalia
• Repetto Cendrillon Ballet Flat in Black, SSENSE
• Compeed Advanced Blister Care Cushions, Walgreens