We Asked These Styling Experts For Their Go-To Loafer Outfits

The precise moment loafers become fashion's must-have shoe depends on who you ask. For some, it may be when the heavy-buckled pairs appeared on the Prada Spring/Summer 2020 runway. For others, it was when Ganni presented its charming take, zhuzhed up with crystals lsat year. What’s not so difficult to determine is why the loafer silhouette's stuck around for as long as it has. Those reasons are more obvious: comfort, a (typically) low heel, a streamlined silhouette. Loafers first rose to popularity in the mid-20th Century with Bass Weejun launching its first men's loafer in 1936. But, over the decades, while the silhouette has remained the same, how to style an outfit around loafers has changed.

While the shoes were a preppy staple of college students and royals like Princess Diana during the '80s and '90s, they’re now known as a go-to design for stylists whose work appears in Vanity Fair or on tour with Beyoncé. But, not only do creatives vouch for the footwear's timelessness, the five stylists below confirm that the shoe is a mainstay of their own closets. What’s more, a sleek loafer — with or without any modern embellishments — is the basis of many modern outfit equations. Ahead, peruse the expert advice on how to wear loafers in 2020 with outfits you'll still love in 2030, 2040, and beyond.

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How To Style Loafers: Layer With A Long Trench

For freelance stylist, creative director, and consultant Slyvie Mus, loafers deserve an uncomplicated approach, with a small dose of quirkiness for good measure. "I like the combination of classic black loafers paired with a long beige trench coat. To give the look more detail, you can add in some colorful socks to bring attention to the space between the loafers and coat,” says the Helsinki, Finland and Paris-based (by way of Rwanda) Mus. “Deep colors like burgundy or navy blue are great for adding detail."

How To Style Loafers: Recreate An Iconic Suit Ensemble

“As a stylist based in New York City, I thrive on assigning classic silhouettes according to every season,” says stylist and photographer Rebecca Alaniz, who takes a nostalgic Hollywood approach. “When it comes to styling loafers, especially during the fall, I know exactly where to find my styling recipe ... please see: Sally Albright, the New York muse herself, from the romantic comedy hit classic, When Harry Met Sally. This film is a cinema encyclopedia for fall wardrobe in New York, an invitation to quintessential styling ideas.”

For fall, Alaniz says she’s all about Albright’s neutral-based, strong-silhouetted, ‘80s looks. “I immediately gravitate towards semi-dark khaki oversized suiting, most likely vintage, layered over a cream toned cashmere turtleneck. This look would not be complete without the pairing of my chocolate brown vintage Gucci loafers and my favorite Frances Austen cashmere cream socks,” she says, outlining her ensemble as well as a coordinated activity. “Fully dressed and comfortably in my loafers, I’m ready to take on Harry and Sally’s weekend tour through New York’s finest spots. Meet you at the Met Museum for a stroll, and Kat’s Deli for lunch.”

How To Style Loafers: Pair With Luxe, Relaxed Silhouettes

“A classic loafer will always be on-trend, so my favorite way to style them this season is the way I’ve always worn them,” explains Courtney Madison, an L.A.-based stylist who’s notably worked alongside Beyoncé, Rihanna, and Mindy Kaling. “My dream fall outfit would be an oversize cashmere turtleneck with a wide leg cropped trouser paired with a timeless loafer.”

While Madison stands behind this relaxed and luxe combination, she also stresses the importance of thoughtful purchasing and care with forever wardrobe staples, like loafers. “When it comes to shoes, I always try to buy better where possible. Your back will thank you and if they are made from quality leather you will have them for years to come with the help of a cobbler.”

How To Style Loafers: Polish Up A Jeans-And-Tee Look

With a resume that includes work at Vanity Fair, Aritzia, and Everlane, Patricia Lagmay is an L.A.-based stylist who shares that she’s practically a lifetime loafer wearer. “I don't think I've ever not owned loafers, childhood aside,” she says. With a wardrobe that relies heavily on tailored silhouettes and minimalism, Lagmay pulls a bit of ‘90s inspiration in her approach to styling the practical and polished shoe. “I'm partial to a classic black or dark mahogany pair in shiny (but not quite patent!) leather, with a white tee, vintage jeans, and an oversized men's blazer. It's easy and casual but still put together,” says the stylist and thrifting aficionado. “I'll add in white socks if it's especially brisk out to just really nail in the ‘90s dictum.”

How To Style Loafers: Swap In For Sneakers

For celebrity and editorial stylist Britt Theodora — her clients include Shira Haas, Perry Mattfeld, Sofia Bryant, and Paige Hurd — loafers make for a chic replacement where you might normally choose sneakers. "Loafers are the perfect shoe this fall because they are comfortable and I am a huge fan of menswear-inspired looks," she says, specifically calling out Brother Vellies who makes a silhouette to pair with her fall uniform. "My favorite way to style these are with a fun poncho layered with a more form fitting knit underneath and leggings," she explains. "Ponchos are a fantastic accessory for all of the outdoor excursions this season. They can fit over a coat and provide added warmth!"