A Chelsea boot is a close-fitting, ankle-high boot with an elastic side panel that allows for easy pulling on and off. They often have a loop or tab of fabric on the back of the boot, enabling the boot to be pulled on. The boot dates back to the Victorian era, when it was worn by both men and women. The term "Chelsea boot" emerged a few years before the beginning of the Victorian era, becoming a name used by London cobbler Thomas Cotton by 1831. Charles Goodyears development of vulcanized rubber enabled the invention of the elastic gusset boot, which meant they could be easily removed and put on again. By the late 1840s, the fashion began to catch on, and Chelsea boots became a prominent style in the West until the onset of World War I.

In the 1950s and 1960s, Chelsea boots became popular in the UK, and their association with the Kings Road (a street in Chelsea and Fulham in inner western London) set of Swinging London is believed to explain how the name Chelsea became attached to the boot. Chelsea boots were worn by everyone from the Rolling Stones to Jean Shrimpton. Theatrical and ballet shoe maker Anello & Davide created a variant of the Chelsea boot in 1961 with Cuban heels and pointed toes for the Beatles, after John Lennon and Paul McCartney saw some Chelsea boots in its shop window and commissioned four pairs with higher, Cuban heels – this style became known as Beatle boots. Beatle boots, as were Chelsea boots, were frequently adopted by mods and worn with tailored suits.

Today, Chelsea boots are popular for their versatility and can be worn as part of formal or casual attire. They are available in a variety of styles, including patent and suede variations, and are designed for both men and women. Timberland is renowned for continuing the Victorian trend of high-quality Chelsea boots, designing them for all occasions, no matter how casual or formal. The classic Chelsea boot hits just a little above the ankle, dipping slightly at its elastic side panels, and sits on a low-to-almost-nonexistent heel, probably taking a cue from men’s footwear. Designers have often reimagined the style, and sky-high shafts and thick platform soles abound now.