14. Leather Loafers

Classic leather loafers are a hallmark of durability and refined style. Crafted using high-quality leathers and traditional construction methods—such as hand-stitching or Goodyear welting—these shoes are designed to last for years. Unlike inexpensive slip-ons, quality loafers can be resoled, extending their lifespan dramatically. Brands like G.H. Bass and Allen Edmonds are known for loafers that become more comfortable and attractive with age, making them a wise, long-term investment.