“My loafers resemble a classic men’s penny loafer, but they really fit and feel like a slipper,” Haller says. Each insider-favorite pair is crafted at an Italian atelier using a Sacchetto construction, the key to a glovelike fit and buttery feel. “They mold to your foot with wear—the shape of the leather becomes your foot which offers comfort and support.” Comfort-first adjustments Haller has made include removing the toe box interlining and heel box, which contributes to the slipperlike vibe, and finishing each shoe with a lightly padded insole.
It’s hard to choose just one style to highlight, but I have to shout out the vintage-feeling colorblock pairs. I can envision them with so many great fall outfits, from neutral sweater sets and denim to printed autumn midi dresses and tights.
Sizes: 36–41
Colors: Brown/bone, black/bone
The Classic Black Loafer
G.H. Bass 1936 Willa Flat Weejun Loafer
The Classic Black Loafer
G.H. Bass 1936 Willa Flat Weejun Loafer
G.H. Bass’s Weejun loafer has been a staple for decades. Fashion insiders and everyday shoppers come back to it time and time again for its classic, flat-strap design and easy-to-break-in construction.
Sizes: 5–11
Colors: Black, burgundy, cognac
Heel height: 0.87"
What reviewers are saying: “This was my first pair of Weejuns in ages, and I’m so happy I came back to wearing them. They’re lovely and very well-made, and the color is perfect. As usual with good leather shoes there’s a short break-in period. That passed quickly, and now they’re my daily shoe (outside of inclement weather).”
The Lug-Sole Loafer
Madewell x G.H. Bass Larson Weejuns Loafers
The Lug-Sole Loafer
Madewell x G.H. Bass Larson Weejuns Loafers
Credit: Madewell
Madewell updated its footwear lineup for fall with a special G.H. Bass collaboration. This fresh pair has the same flexible upper that Weejuns fans will recognize, plus a supportive, treaded lug sole that’s up for striding through the city. More than 200 other shoppers have added them to their cart in the past week—so it’s safe to say they’ll become a collector’s item soon.
Sizes: 7–13
Colors: Black, green
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The Slip-On Loafer
Franco Sarto Bocca Slip-On Loafer
The Slip-On Loafer
Franco Sarto Bocca Slip-On Loafer
Credit: Franco Sarto
Ultimately, the most comfortable loafers are shoes you don’t have to overthink. This pair by Franco Sarto is a prime example. Its inky midnight blue leather is an alluring twist on the usual neutrals, and the low heel adds just enough lift. Slip them on and go.
Sizes: 5–13
What reviewers are saying: “Most comfortable dress shoe I have ever worn! Love the classic style. Fit perfectly.”
The Color Trend Loafer
Tory Burch Perry Loafer Flats
The Color Trend Loafer
Tory Burch Perry Loafer Flats
Credit: Bloomingdale's
I think fall 2023’s biggest color trend is best embraced with an accessory: either a red designer bag to pop against a neutral coat or a pair of bright loafers like this Tory Burch pair. These have a low, walkable heel, a flexible upper, and a tiny logo embellishment that shines against the cherry red leather.
Sizes: 6–11
What reviewers are saying: “They are soft, comfortable and the quality met my expectations. The color is beautiful the leather is soft but the sole is sturdy, yet the inner cushion is comfortable…well worth the cost.”
The Croc Embossed Loafer
Emme Parsons Danielle Loafer
The Croc Embossed Loafer
Emme Parsons Danielle Loafer
Credit: Emme Parsons
Emme Parsons is one of my favorite designers for shoes that I can wear on almost any occasion while still feeling more elevated than I do in a regular-old “classic.” I have these loafers on my fall wish list after wearing the brand’s Susan sandals all summer.
If “going-out loafer” isn’t a shoe category yet, I’m making it one with this pair. The croc embossed leather feels dressy enough to wear out to a candlelit dinner with a silk LBD and little ankle socks, yet it can also spruce up my T-shirt and trouser outfits for work.
Sizes: 35–42 IT
Colors: Espresso croc, black croc
Heel height: 1"
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The Chunky Square-Toe Loafers
Me+Em Square-Toe Loafer
The Chunky Square-Toe Loafers
Me+Em Square-Toe Loafer
Credit: Me+Em
While the shape of a square-toe loafer naturally gives our feet more space to stretch out, Me+Em’s pair goes the extra distance to deliver on comfort in addition to its cool, modern design. The height of the tongue is precisely cut to keep from digging into any ankles, and there’s a non-slip insole for easy walking (or power-walking when the day gets busy).
Sizes: 37–41
Colors: White, snake print
The Luxe Black Loafer
Saint Laurent Le Loafer Moc Toe Penny Loafers
The Luxe Black Loafer
Saint Laurent Le Loafer Moc Toe Penny Loafers
Credit: Bloomingdale's
Saint Laurent’s take on the penny loafer hits all the classic notes the best styles include. It differs in two key areas: a special decal along the back heel and several reviews from other shoppers praising its comfort level.
Sizes: 5–11
Colors: Shiny black leather, matte black leather
What reviewers are saying: “Perfect. I recommend to anyone looking for a timeless classic that is beautifully made and comfortable. I wear a size 9 and it was nice and snug. Which is how I love to get penny loafers because they stretch as you break them in!”
The Tassel Loafer
Celine Luco Loafer With Triomphe Tassels
The Tassel Loafer
Celine Luco Loafer With Triomphe Tassels
Credit: Celine
I see Celine’s loafers almost daily–they’re a particular favorite of the Bazaar accessories team. It’s in part because the low-heeled, buttery leather design feels like a slipper, and in part because the tassels on top are just plain charming.
Sizes: 34–42
Heel height: 15mm
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The Velvet Loafer Slipper
Vibi Venezia Velvet Slippers
The Velvet Loafer Slipper
Vibi Venezia Velvet Slippers
Credit: Net-a-Porter
Slipping into Vibi Venezia’s velvet slipper feels like a staycation at the Plaza. Okay, that’s a slight exaggeration—but the lush velvet and grosgrain trim feel so luxuriously soft. There’s a rubberized sole, too, so you can take the elevated pajama dressing vibes out of the house. (P.S. Bazaar editors are also fans of the label’s velvet Mary Janes.)
Sizes: 35–41 IT
Colors: Blue, burgundy, emerald, and more
The Suede Pointed Loafer
Margaux The Penny
The Suede Pointed Loafer
Margaux The Penny
Now 20% Off
Credit: Margaux
Margaux’s shoes have never let me down where comfort is concerned. From the label’s signature ballet flats to these ideal-for-fall suede loafers, every pair has a flexible, non-irritating outer and five millimeters of cushioning throughout the sole. Put simply, they’re the sort of loafers you can wear for hours on end as soon as they arrive.
Sizes: 3–14
Colors: Caramel, black, navy, and more
What reviewers are saying: “I was debating between these and another brand that offered a similar color/style. I’m glad I chose these! They’re so comfortable and they fit my life and style perfectly.”
The Elevated Horsebit Loafer
Gucci Jordaan Loafer
The Elevated Horsebit Loafer
Gucci Jordaan Loafer
Credit: Gucci
I’ll always have a soft spot for my pair of black Gucci Jordaan loafers. They were the first designer shoe I ever invested in. A few years have passed since my big purchase, and they’re still as soft and refined as the day I bought them—they’re a luxury investment that lasts. For a slight update, I have my eye on this updated version for fall 2023. It has the same house signature hardware and low heel, plus an on-trend metallic leather and glitzy crystal embellishments on the horsebit.
Sizes: 4–12
Colors: Gold, pale pink, white, black
Heel height: 0.6"
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The Loafer Kitten Heel
Aera Grace Heel
The Loafer Kitten Heel
Aera Grace Heel
Credit: Aera New York
At a recent appointment to preview Aera’s fall and spring shoes, it took about 0.5 seconds for me to become smitten with these loafer kitten heels. First, because the quilted insole is springy, soft, and comfortable enough to wear for a full day at work (even with that slight pitch from the heel). Second, because the Grace Kelly–inspired slingback design is so sharp—I know I’d feel instantly more confident wearing these to the office.
Sizes: 5–12
Colors: Black, cuoio, orange
Heel height: 45mm
The Split-Toe Loafer
Maison Margiela Green Tabi Loafers
The Split-Toe Loafer
Maison Margiela Green Tabi Loafers
Credit: SSENSE
I know Tabis aren’t for everyone. But if the cult-favorite split-toe has already won you over in flat form, a loafer rendition also belongs in your closet. The design is as ergonomic as it is avant-garde, with plenty of space for your toes.
Sizes: 35–41 IT
Heel height: 1"
The Embellished Loafer
Nomasei Nono Loafer
The Embellished Loafer
Nomasei Nono Loafer
Credit: Nomasei
Nomasei’s design is so distinct, a supermodel paused me while I was interviewing her to ask where they were from. (She then made a note of it on her phone.) The square-toe shape creates extra wiggle room in the toe box; the leather is also a breeze to break in with thick socks. (Not that it takes much work!) For me, the detail that makes these comfortable loafers a win is the brass embellishment on the upper band. Its raised-hand logo is kind of like a benediction, blessing anyone who wears these loafers with a complete look.
Sizes: 35–42
Heel height: 3cm
What reviewers are saying: “Just received these beautiful shoes! The fit is perfect! They are so elegant.”
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Why trust Harper’s Bazaar?
For more than 150 years, Harper’s Bazaar has been the preeminent fashion, beauty, and lifestyle resource for women at every age. We cover what’s new and what’s next in fashion by working with the world’s leading authorities in ready-to-wear, footwear, accessories, and more. Every story we publish has been thoroughly researched and vetted by our team of editors and industry experts.
Halie LeSavage is the fashion commerce editor at Harper's BAZAAR. Her style reporting covers everything from reviewing the best designer products to profiling emerging brands and designers. Previously, she was the founding retail writer at Morning Brew and a fashion associate at Glamour.
Are lofar shoes formal?
You can wear loafers for formal and casual wear, as they come in many different materials; when made out of leather, loafers serve as a good pair of dress shoes, and those made of fabric can be for smart casual wear. Loafers are versatile, comfortable, and easy to take on and off.
Are chunky loafers fashionable?
A trusty chunky penny loafer is a true closet staple. It's a trusty loafer style that can be worn through all seasons and complete just about any outfit.
How do you wear elegant loafers?
Loafers combined with a skirt make a wonderful classy look. For a chic look, an A-line skirt, flared skirt, or pleated skirt will look brilliant, especially when combined with a blouse or a sweater. A long flowy skirt combined with loafers also makes an effortless and stylish outfit.