Jessie Quinn and Courtney Leiva are contributing writers for PEOPLE who reviewed testers’ insights to learn more about their experiences with each style selected and how well the Chelsea boots held up during the two-week testing period. They also spoke with fashion stylists to gauge how to choose a pair of Chelsea boots and what standout features to look for.

Chelsea boots are the ideal shoe style for transitional weather.

The shoe, named after the posh neighborhood in London, originated in the early 1800s but shot to fame when popularized by the Beatles in the late '50s and '60s. The style has since evolved to include boots with chunky soles, tall heels and shafts, and some Western details , while keeping the traditional elements like stretchy gore side panels alive.

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