The 16 Best Loafers to Round Out Your Winter Wardrobe

They're all fashion insiders want to wear—now and always.

A collage of three women at fashion week wearing loafers
(Image credit: Getty Images)

Lofty words like "timeless" and "classic" fall short of capturing the very best loafers’ appeal. More than a seasonal shoe trend, the academia-inspired silhouette comes with a lifestyle attached, one you can wholly lean into or subvert on your own terms when you style your favorite option into a cute loafers-centric look. This winter, the best loafers are a foundational option in my footwear collection. I wear them even more often than my favorite pair of white sneakers, especially when I team them with a pair of socks.

The best loafers stick with you. There’s a reason they tend to pop up in discussions around “cores” and aesthetics: While they have a distinct look, they’re a piece that knows no season or trend. Instead, they grow with you as you develop your sense of personal style.

Laurel Pantin, a longtime loafer fan, author, and writer behind the Earl Earl newsletter, knows the style’s enduring charm well. “When I was in high school, I bought a pair of gold loafers at a thrift store in my hometown. This was in 2002—metallic shoes were not a thing,” she tells Marie Claire. "They were honestly kind of orthopedic and granny, but I loved them and wore them nonstop. I became kind of known for them at my school—so much so that my AIM screen name was GoldenLoafers." After a few years’ hiatus, Pantin fell back in love with the style—she now counts subtler options like The Row’s best-selling Soft Loafers as a constant standby.

The moral of this shoe story: Even if you outgrow the metallic loafers of your youth, they will always have a home in your closet in one form or another. Ahead, Caroline Maguire, Senior Fashion Director at Shopbop, also offers her take on the top trending pairs (and brands to keep an eye on) for the year, alongside plenty of styling tips to keep in mind as you incorporate them into your routine. Consider this the time to find your One True Pair.

The Best Loafers at a Glance

Marie Claire's Favorite Loafers

Shop the Best Loafers

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What to Look for in the Best Loafers

  • Quality: Loafers have the potential to be the foundation of your footwear wardrobe, so invest in a pair that will truly last. Some brands have a rich history of creating high-quality loafers, like Gucci, which first released its leather horse-bit loafer in 1953. All those decades of experience—and an emphasis on handmade designs—mean the label's pairs will endure from season to season. Capital-D Designer brands aren't the only ones who've mastered quality. G.H. Bass's loafers are often under $200—and they're credited as the first-ever penny loafer in fashion, released in 1936. More affordable brands like Sam Edelman and Vagabond Shoemakers are also careful to craft each pair with long-lasting details like padded footbeds and supportive soles.
  • Silhouette: As Pantin notes, the best loafer silhouette is the one you'll actually wear (and in more than one way). If you're ready to branch out from the typical penny loafer silhouette, there are other styles to play with. Celebrities like Taylor Swift have endorsed heeled loafers for extra height, and designers like Tory Burch have dreamed up silhouettes that combine the ease of a ballet flat with the structure of a loafer. Maguire also says that designers like Jamie Haller (which makes our best overall option) makes the cool-girl approved loafers you should know about.
  • Comfort: All and all, Pantin's number-one priority with loafers is true for every style of shoe: She's looking for comfort first. "They're everyday shoes, so they need to be able to be worn every day without killing your feet," she explains. Consider the amount of arch support, the thickness of the sole, the heel height, and the materials used to determine if a pair of loafers will deliver a wear-all-day feel for you.

How to Style Loafers

Because loafers are endlessly versatile, you don't have to overthink styling them. Celebrities like Kendall Jenner and Alexa Chung have mastered the art of the off-duty loafer, for instance, so look to either new-age style icon for outfit inspiration.

Jenner owns several pairs of black loafers, and styles each pair differently. She teamed a patent pair with a Reformation mini skirt and a sweater vest for the perfect high-low preppy look, and teamed a pair of The Row's Soft Loafers with an equally-luxurious jacket from the Olsen-twin-founded brand once the weather had changed. Chung, however, opted for a classic trench-coat-and-jeans combination, which is one I fall back on when I don't know what to wear.

Taylor Swift also put her spin on the loafers trend in late 2023, wearing a heeled pair while out to dinner with Gracie Abrams (also in a pair loafers) in New York City. Swift styled them with sheer black tights, a white skirt, and a navy blue blazer—the perfect way to transition your loafers from winter to spring. It's a look she's copied since, marking it as a signature aspect of her current wardrobe era.

Kendall Jenner, Alexa Chung, and Taylor Swift and Gracie Abrams all style loafers.

Taylor Swift and Gracie Abrams coordinated in old-fashioned loafers on a fall outing in New York City.

(Image credit: Getty Images; Backgrid)

If you've mastered the classic look and want to branch out, Maguire recommends thinking outside of the box with your styling techniques. Socks are a go-to accessory, she says, but she also loves to wear them with trendier clothing pieces. "Try pairing them with a bubble or a-line circle skirt for a more preppy or dressed-up look," she says.

Meet the Style Experts

Laurel Pantin
Laurel Pantin

Laurel Pantin is the Los Angeles-based author of style newsletter Earl Earl, a branding and creative consultant, and personal stylist. She is a former fashion editor who previously held roles at InStyle, CoveteurLucky, and Teen Vogue. 

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Julia Marzovilla
Fashion E-Commerce Editor

Julia Marzovilla is the Fashion E-Commerce Editor at Marie Claire, where she reviews the latest launches from fashion and beauty brands, finds the best on-sale items around the internet, and interviews experts to find the best products in any category to share with her readers. She also creates shopping guides that span every vertical on the site as an expert in everything from the best laptop bags to the best laser hair removal devices.

In her near decade of experience, Julia has both written for several top outlets in the E-Commerce space and worked at major fashion labels. Prior to joining the Marie Claire team, she contributed similar shopping stories to sites such as Bustle, InStyle, The Zoe Report, Who What Wear, and worked as the Trending Fashion and News Writer STYLECASTER. You can find her across the internet at @JuliaMarzovilla. In real life, you can find her creating shopping guides for her friends, cooking or baking in her too-small kitchen, or buying tickets for the next time Harry Styles is in town.

Julia has a Bachelor’s degree in English with a minor in Journalism from Loyola Marymount University in Los Angeles, California. She lives in New York City, her hometown.

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