The products and services mentioned below were selected independent of sales and advertising. However, Simplemost may receive a small commission from the purchase of any products or services through an affiliate link to the retailer's website.
Ah, penny loafers. Like tweed jackets and Oxford button-down shirts, they are a classic fall staple of the preppy set.
Recently, though? Loafers are showing up in places far beyond the country club. Even during the hot summer, they’ve become the shoe of choice for fashion-forward types like Hailey Bieber, Dakota Johnson and Sophie Turner. And Vogue is calling the sturdy shoes a “fashion-girl favorite.”
MORE: The Best Shoe Storage
“Some classic items have always been geared toward people who dress in a classic way, who can keep the same things in their wardrobes for years and years,” New York City-based wardrobe stylist Diane Pollack of Stylempower tells Simplemost. “But sometimes a designer will put that item on a runway, and suddenly it’s everywhere. It gets regenerated. Definitely, loafers are newly trendy.”
And how are fashion insiders wearing loafers these days? Hallie Abrams, a Cleveland, Ohio-based stylist and founder of The Wardrobe Consultant, says you’ll be seeing a lot of loafers paired with socks this season — though she also adds that “a loafer with no socks will always be a timeless choice.”
MORE: The Best Chunky Loafers
Here are some great loafer options for the fall, plus some expert tips on how to incorporate them into stylish outfits.
“I love the look of loafers and socks,” says Abrams. “It gives the feel of a bootie. And it’s fun and flirty. Red is also a big color for fall 2023, so this is a nice way to bring red in without having a full red outfit.”
In the photo above, the chic model has an all-white, light and airy look — which you typically wouldn’t pair with dark, heavy-looking loafers. Pollack points out that while “effortlessly stylish celebs and models are all about breaking the rules to be stylish,” you don’t have to. To balance out the light colors with this very dark shoe, she suggests adding jeans to the mix.
Buy Bibi Lou Jaya Loafers in black, silver or gold at Anthropologie for $180.
The photo above is a perfect example of designers finding new ways to make a classic loafer more modern.
“Metallic leathers are really trendy right now,” Pollack says. “I’ve definitely been sending my customers a lot of those. Also, note the chunkier heel and the oversized hardware in a contrasting metal.”
While Abrams says that “mesh or fishnet socks with loafers or even sandals are very fashion-forward,” she notes that it’s just one way to style these. Another option?
“I would wear these with no socks,” Pollack says. “And they would look cute with jeans or with a skirt.”
Buy Caverley Star Loafers at Anthropologie for $210.
In the photo above, the model is wearing “a twist on a classic,” Pollack says. An Oxford button-down and tweed jacket are updated with shorts and socks with loafers. Pollack adds that another way to refresh the classic loafer look is to wear them with modern, oversized trousers.
“If the idea of socks with loafers scares you a little bit, try something monochromatic like this,” Abrams says. “It feels a little more accessible because it looks more like a boot as opposed to a sock with a shoe.”
Buy Winona lug-sole penny loafers in suede at J.Crew for $228.
“While loafers are traditionally more of a flat shoe option, we are seeing lots of different iterations, like this chunky heel loafer,” Abrams says. “It looks great with slacks or jeans. And ladies that love wearing heels looove these.”
One of the appealing aspects of these shoes is the many ways you can style them.
“You could wear these with jeans and trousers or cute skirts,” Pollack says. “Play with a classic pleated skirt or an A-line plaid skirt — take that classic style and make it modern.”
Buy Dream Pairs Women’s Dressy Chunky Loafers on Amazon for $25.99 (was $36.99).
This may be a more classic-shaped loafer, but it’s miles from boring! Abrams says that the style reminds her of “old-school Bass loafers,” but has gotten a great update with the sunshine yellow color and patent leather look.
“What a fun way to add a pop of color to an outfit,” she says.
And these affordable patent leather loafers (currently on sale for 22% off) come in a range of colors — including a shiny purple.
Buy Caradise Women’s Patent Leather Loafers at Amazon for $34.99 (was $44.99).
You can spot Doc Martens a mile away with those yellow-stitched rubber soles. While the British company is most famous for clunky boots, it’s right in the midst of the current loafer trend. The version above adds a classic floral jacquard fabric to the grungy cool of this brand — a twist on a classic in more ways than one!
Buy Dr. Martens Penton Floral Jacquard Loafer at Urban Outfitters for $150.