On March 9, 1876, George H. Bass began making shoes in Wilton, Maine. The brand's own timeline puts the beginning there, before the Weejun had a name or a penny keeper. In 1936, Bass introduced Weejuns, inspired by and named after a Norwegian farmer's slip-on, and that is the thread I want to follow: a shoe built to move between a working origin and a college wardrobe.

An Esquire team spotted Norwegian slip-ons in Palm Beach in 1935, and Bass was commissioned to recreate the style. On campuses, students put coins into the strap's diamond cutout, and the penny loafer got a name of its own. By the late 1950s the penny loafer was a collegiate standard; the Ivy look carried Weejuns beyond American campuses in the 1950s and early 1960s. I like the two-step history: a local Maine shoemaker, then a shoe that traveled without laces.

Start with the black Whitney Weejuns: hand-sewn moccasin seams and beefroll detailing give the plain penny strap enough detail to read clearly with navy trousers and a white shirt. The wine version would bring a warmer note under a gray suit, while the light-brown and cream Whitneys have softer contrast with dark denim or wool tights and a skirt. I would keep the black and white pair for a graphic outfit and olive for a more muted one. Before choosing a color, I would compare its vamp against the hem I plan to wear most; the toe and keeper are the focal point, so the trouser should stop without swallowing them.

A thicker sole changes the line of a loafer before it changes the outfit. The black Whitney Superlug keeps the penny strap and moc toe shape, with a chunky sponge rubber sole; the wine version gives the same outline a deeper red-brown note. I would put either under straight jeans or a long skirt so the heavier base has some room.

The black Rosamund adds vintage-inspired monogram hardware and a raised heel, and antique brown softens that detail while keeping the sponge rubber outsole. For a more open front, the off-white Fisherman Mary Jane has a woven vamp and buckle strap; the medium-brown version warms up the same texture. The black Fisherman Mary Jane keeps the weave but makes a stronger contrast with dark tights. With a plain crewneck and cropped trousers, I would let the shoe do the talking; with a skirt, sheer tights keep the strap visible.

The penny keeper makes these feel related to the classic Whitney, but the sole and strap placement change the silhouette. Before buying, I would check that the buckle sits comfortably across the instep and that the heel does not lift as I walk around the fitting room. What I would skip: the off-white woven Mary Jane if the rest of the outfit already has a busy knit or print; the strap and vamp have plenty going on without competition.

A 1980 style guide reported that preppy Americans were buying Weejuns as quickly as the company could make them; the tassel versions are a more decorated branch of that campus story. The black Esther keeps the hand-sewn moccasin seams, beefroll edge, and twin tassels under a kiltie; wine and dark-chocolate Esther versions repeat that front in warmer shades.

The black Anita is quieter at the toe, with small gathered accents and a memory-foam insole. Medium brown keeps the same glove-soft upper, and the antique-brown suede option lets texture do the talking. Margot in black and light brown wears tassels with a sponge rubber outsole, so I would pair it with ankle-length trousers, a chunky knit, or a clean denim skirt rather than add another ornament.

Tassels can tip formal fast. I would check that they sit evenly and that the kiltie lies flat before choosing an Esther. What I would skip: the kiltie front if I want a very spare, uninterrupted line under a narrow trouser. The Anita or Margot is the calmer choice for that outfit, while the wine Esther can hold its own with a plain skirt and tights.

Color is easier to judge next to the clothes I actually reach for, not in isolation. The taupe suede Wallabee, made with suede from English tannery Charles F. Stead, reads softer beside camel or brown tights; the black box-leather version looks sharper with gray flannel. Both use the Clarks Originals last and a natural crepe outsole.

The natural leather Mary Jane has a buckled T-strap, while the dark-chocolate Rose adds a gathered toe and branded coin detail. Antique brown Rose gives the same gathered front a worn-in color. For a more straightforward penny shape, the Bordo Blythe has a whale-tail keeper and flexible rubber outsole; light-brown Grace brings two-tone burnished leather; wine Rumi trades a classic heel for a scrunch back and softer upper.

This is where I would decide whether I want the heritage reference to be obvious or only suggested. I would check the suede in daylight, look at the grain and color across both shoes, then try the strap with the hem I plan to wear. I would skip the wine Rumi if I wanted a crisp, tailored finish; its gathered heel and soft upper suit a looser outfit better.

By 1980, one Toledo style guide had penny loafers in its list of women's prep clothes, alongside blazers, sweaters, oxford shirts, and slacks. I like that the shoe was not only a men's campus shorthand; these options make the same coin-slot idea easy to take in a different direction.

The black Temara from Dr. Martens has polished leather, a broad strap, apron toe, and grooved rubber sole; cherry red gives it a brighter edge. Sam Edelman's Lizbeth comes in bamboo-brown or black suede, with a gathered moc toe and low heel, so I would set it against dark denim or a gray skirt. Cole Haan's black croc-print Treena brings a chunky lug sole and a raised profile; Steve Madden's Madison keeps a one-inch heel with a more understated apron toe in black leather or red suede. Tory Burch's cocoa Classic Penny Loafer ends on a lower profile, with a logo coin keeper.

I would compare the upper across all pairs at eye level, then check the vamp against my instep and the sole against the day I am dressing for. A dressier shoe can still feel relaxed with straight-leg pants; a lug sole asks for a longer hem or a deliberately heavier sock.

I would choose in this order: a black or wine Whitney if I want the original penny-strap outline; a Superlug or Fisherman Mary Jane if I want the sole to announce itself; then a tassel, suede, or color if I want the front to do more work. The coin-slot story stays useful not because I need to carry change there, but because one small cutout turned a practical-looking shoe into a shorthand for how people dress.

If I could keep one reference in mind, it would be Wilton in 1876: a town and a shoemaker before the shoe became everybody's campus shorthand. I would pick the pair that makes tomorrow's outfit simpler and let the rest of the story travel with it. If you want to keep browsing, I also put together Black Loafers and YSL Loafers Dupe.