This pair of men’s mules features high flared heels in keeping with turn of the 18th century fashion. The red leather covering the high heels was meant to bring attention to them and also a conveyed a sense of continental sophistication as red heels were famously worn in the court of French King XIV.

The 1970s saw many fashionable men reintroducing heels into their wardrobes. Celebrities like Elton John strutted on stage in outrageous outfits and high glittering heels such as this pair but more conservative men also paired higher heeled shoes with their suits.

Ever since the introduction of the heel in Western dress in the late 16th century, heels on riding boots have been a matter of both fashion and function. This sturdy boot from the turn of the 18th century features a high stacked leather heel.

The Toronto shoemaker Master John made these men’s platform boots complete with five and a half inch heels, appliquéd stars, and veritable landscape in leather. In the 1970s, some men followed the lead of rock stars in adopting lavish personal adornment and elevating shoes cultivating a persona at once dandyish and hyper-masculine.

Cowboy boots are icons of rugged individualism and masculinity, qualities that they are able to convey even though they feature heels of significant height. The cowboy emerged in the West after the Civil War pushing cattle to railheads in the 1860s to 1880s. Their time on the open range was short lived and their numbers were few but their image and the boots are seared in our imaginations.