The Colorblock Loafer

Jamie Haller Two Tone Penny Loafer in Brown and Bone

The Colorblock Loafer

Jamie Haller Two Tone Penny Loafer in Brown and Bone

“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 Elevated Horsebit Loafer

Gucci Jordaan Loafer

The Elevated Horsebit Loafer

Gucci Jordaan Loafer

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 Chunky Square-Toe Loafers

Me+Em Square-Toe Loafer

The Chunky Square-Toe Loafers

Me+Em Square-Toe Loafer

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 Color Trend Loafer

Tory Burch Perry Loafer Flats

The Color Trend Loafer

Tory Burch Perry Loafer Flats

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 Loafer Kitten Heel

Aera Grace Heel

The Loafer Kitten Heel

Aera Grace Heel

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

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The Croc Embossed Loafer

Emme Parsons Danielle Loafer

The Croc Embossed Loafer

Emme Parsons Danielle Loafer

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"

The Velvet Loafer Slipper

Vibi Venezia Velvet Slippers

The Velvet Loafer Slipper

Vibi Venezia Velvet Slippers

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

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.”

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The Split-Toe Loafer

Maison Margiela Green Tabi Loafers

The Split-Toe Loafer

Maison Margiela Green Tabi Loafers

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 Tassel Loafer

Celine Luco Loafer With Triomphe Tassels

The Tassel Loafer

Celine Luco Loafer With Triomphe Tassels

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

The Luxe Black Loafer

Saint Laurent Le Loafer Moc Toe Penny Loafers

The Luxe Black Loafer

Saint Laurent Le Loafer Moc Toe Penny Loafers

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!”

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The Lug-Sole Loafer

Madewell x G.H. Bass Larson Weejuns Loafers

The Lug-Sole Loafer

Madewell x G.H. Bass Larson Weejuns Loafers

Now 27% Off

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

The Embellished Loafer

Nomasei Nono Loafer

The Embellished Loafer

Nomasei Nono Loafer

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.”

The Slip-On Loafer

Franco Sarto Bocca Slip-On Loafer

The Slip-On Loafer

Franco Sarto Bocca Slip-On Loafer

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.”

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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.

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