Think about how your feet adjust to different types of shoes and materials. This will give you an idea of what type of flats may give with time. Leather, for example, tends to soften and stretch over time. “I love a shoe that is comfortable, durable, and chic, so I am always looking for materials that look soft and breathable," Hofstrom said. "I really love the look of patent leather, but they can be a bit stiff, so I gravitate towards softer leather materials, suede, or something with lining. Those softer materials are more comfortable from the get-go and continue to get more comfortable over time with each wear.”