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Having established a successful legacy, the Jackie O has been reimagined for 2025

Pros Made with rich leather, which will last a long time Sole reduces bulk for added flexibility Durable stitching throughout the silhouette Has a removable leather-covered insole for more comfort Cons Only comes in two colors Ecco landed the top spot on the list because the Citytray Cap Toe does an excellent job of concealing all the comfortable upgrades and keeping the appearance of an old school dress shoe

With proper care, a pair of Goodyear-welted shoe can last decades before they need to be replaced

Perfect for minimalists and super modern couples alike