The first shoes worn in the civilized world were probably flats—sandals, to be more precise, similar to the 5,000-year-old antiquities from ancient Egypt. Heels came into vogue sometime in the Middle Ages, reaching the height of their popularity in the 17th- and 18th-century courts of Europe. They might have remained so had Marie Antoinette not worn a pair of high-heel shoes to the guillotine, which soured the public on what was suddenly considered a showy and unseemly shoe.

Flats ruled until the late 1800s, when heels once again came into fashion. But flats never really went away. Two especially ubiquitous types of flats that had a renaissance of sorts at the beginning of the 20th century were the slipper and the espadrille.

In those days, slippers were not just for padding around the house. During the Belle Époque, for example, the practice of sipping champagne from a lady’s slipper was a testament to the quality of the footwear. Some were made of satin, richly embroidered, and trimmed with pleated ribbon. Others were printed in honeycomb or other cheerful patterns, which brought the shoe to the masses.

Contemporary designers who have explored the limits of the slipper include Philippe Model, whose red slippers from the 1980s boasted gold soles and bouquets of satin ribbon. Willy van Rooy also made stylish slippers during the 1980s, using colorful upholstery-like fabrics on the uppers with golden sash-like belts on the vamp.

Andrea Pfister riffed on her own basketweave sandal when she created a spun gold and costume-jewel-studded slipper that resembled a flat mule with an upturned Turkish toe. And in the 1990s, Emma Hope took a men’s black-velvet evening slipper, added a rounded and pointed toe, and applied shimmering hearts and stars to the shoe’s brooding surface.

The espadrille, originally known as the alpargata, was a centuries-old creation of Spanish farmers, who made the soles of these inexpensive, disposable shoes from woven esparto grass, with uppers of cheap canvas. The casual-chic look caught on at Riviera resorts in the early 20th century, when they were renamed espadrilles.

Today inexpensive espadrilles can still be purchased, though most are made in Bangladesh, where plentiful supplies of jute are used for the soles. Despite the shoe’s peasant root...

Another precursor to the flat is the Native American moccasin, which was usually made of deerskin and decorated with beads. These shoes have also been re-imagined, most notably by Italian designer Diego Della Valle, whose Gommino shoe’s sold at his Tod’s stores are a hybrid of the moccasin and the loafer, with knobby non-skid soles and brightly colored suede uppers.

Loafers, of course, are one of the most classic flats. In particular, Belgian loafers have become something of a cult shoe thanks to their restricted supply—if you want a pair you pretty much have to visit one store in New York run by Henri Bendel. Anne Klein and Gucci are two other prominent names in loafers, as is Bass, whose Weejuns from the 1930s set the standard for this archetypal form of footwear.

Even designers best known for their stilettos do flats. Christian Louboutin’s are dyed in purple, red, or yellow, after which they are covered with spikes. And Manolo Blahnik’s slippers often drip with costume jewels until they resemble a Miriam Haskell or Trifari confection from the 1930s, ’40s, or ’50s.

Of course, designers like Louboutin and Blahnik are best known today for supplying high-heeled creations to pop and movie stars, but there was a time when Hollywood was infatuated with flats. In fact, the year can be precisely dated to 1957, when Audrey Hepburn starred in “Funny Face,” which paired the actress’s tapered Capri slacks with Capezio ballet flats.

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