This preppy staple is a ’90s revival that's here to stay.
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Synonymous with academia, loafers are often overlooked as the preppy grandma shoe you want to steer clear from. It’s time to cast those thoughts aside because the standard penny loafer you wore in elementary school has endured a total makeover. These days, chunky loafers are the unofficial supermodel off-duty look — just ask Kendall Jenner and Hailey Bieber. Plus, the loafer resurgence brought with it a truly massive variety of styles and design details, like thick, exaggerated straps, spunky metal hardware, trendy cutouts, and just about every finish you could want. But the best news? There's really no wrong way to do it. The only true tragedy here would be to only choose one style.
What We Love: These celebrity-loved shoes are both extremely durable and comfortable.
What We Don’t Love: They aren’t offered in half-size options.
We often turn to celebrities to find the latest and greatest brands, and when it comes to shoes, they all seem to be a magnet for this Vagabond style. Emma Chamberlain, and Naomi Watts are just a few who have been spotted traipsing around in the label’s creations. To finally see what the hype was about, InStyle commerce writer Tamim Alnuweiri tested the 2.0 Platform Tassel Loafer, a style that Jenner has been wearing non-stop.
As a self-proclaimed Dr. Martens loyalist, Alnuweiri didn’t think this pair could compare to her chunky-soled favorite. But after taking the time to break these leather babies in, they’ve become her most worn — and new favorite — pair of shoes. When it comes to style, she finds that the shiny black leather goes with almost everything in her wardrobe and the thick 1.75-inch lug-sole makes them look cool and definitely less matronly than traditional loafers. Plus, the tassel adornment is fun.
The shoes really shine when it comes to functionality and durability. Alnuweiri appreciates how they support her heavy gait and that they feel much lighter than they look. Over several months they have maintained their shape and kept her feet feeling comfortable, even after 16-hour days. However, the crowning detail may be the fact that they can withstand the wear and tear of the New York City streets, which are known to devour even the toughest soles in record time.
The one thing that would make these shoes better is the sizing: They’re currently offered in whole sizes, so it makes finding the perfect fit a bit of a trial and error process.
Price at time of publish: $105–$200
Size: 6–11 | Materials: Leather upper, rubber sole | Colors: 2 | Heel: 1.75 inches
What We Love: Despite the chunky heel, these shoes don’t feel weighty.
What We Don’t Love: They are a bit big, so you’ll need to size down.
While many high-quality loafers clock in at well over $200, the Crown Vintage Sage Penny Loafer will cost you less than $100 (and they don’t skimp on construction or style). With a traditional penny loafer design on top of a 2.5-inch heel, we consider these to be an edgy remix of the timeless preppy style.
InStyle’s former commerce editor, Mary Honkus, counts herself as one of the loafer’s biggest fans. “Despite being, well, chunky, these are surprisingly lightweight and painless to wear,” she shares. “I love that the block heel adds a bit of height without making me feel like I’m towering over everyone, and the padded footbed keeps my feet comfortable as I run around New York City.”
Swapping true leather for a synthetic option — a detail which not only slashes the price, but also makes them a cinch to care for, a crucial detail if you opt for the lighter toned option. To boot, Honkus adds that the shoes have held up extremely well over the course of a year. “They're also super easy to style,” she says. “I've really been leaning into the trendy Gossip Girl school girl look and have paired them with a plaid skirt, cashmere sweater, and blazer. But really, the styling options are endless.”
Price at time of publish: $60 (originally $80)
Size: 6–11 | Materials: Synthetic leather upper, rubber sole | Colors: 4 | Heel: 2.5 inches
What We Love: If you’re going to invest in a designer loafer, make it this iconic pair with the flashy, instantly recognizable horsebit hardware.
What We Don’t Love: The shoes run slightly small.
We don’t take our investment purchases lightly; they must be worth every penny to be considered. And no one makes loafers as well as Gucci when it comes to quality, craftsmanship and longevity.
Constructed from 100 percent Italian leather, these contemporary kicks were modeled after the brand's original loafers from the 1950s, but feature a few new twists, namely, the 1.5-inch rubber lug-sole. This seemingly minor detail revamps the entire silhouette for an easy, slip-on style that adds an edge to any outfit. A gold toned embroidered bee on the heel is a glamorous, yet subtle, update and we just can’t get enough of Gucci’s celebrated horsebit.
Unsurprisingly, these were built to last. Once you find the right size (they’re European sizes and run small — size up), they will be a mainstay in your wardrobe for decades.
Price at time of publish: $1,150
Size: 4–12 | Materials: Leather upper, rubber sole | Colors: 1 | Heel: 1.5 inches
What We Love: These shoes were made for walking: After breaking them in, we logged thousands of steps without any issues.
What We Don’t Love: The need for breaking them in cannot be overstated.
We love loafers for their timeless appeal. But that doesn’t mean we don’t also adore the latest iterations with punchy details, which is why this pair from Sam Edelman has our hearts — it offers a bit of both, as it offers the structure of a traditional loafer, but with contrasting stitching and golden hardware.
We’re happy to report that the loafers offer much more than just looks. InStyle writer Irene Richardson says these are one of her finest adult purchases. “When I went searching down the online loafer rabbit hole, I sought something affordable and versatile, and it needed to transition seamlessly between seasons. I’m happy to report this pair checks all those boxes,” she says. “They go with everything in my closet, but I’m mostly in love with how their chunky platform provides a bit of heft that deviates from preppy styles.”
If you walk to work, Richardson says these have got you covered once they’re broken in (which does take a few wears). “They’ve turned out to be quite the commuter shoe,” she says. The shoes don’t squish my feet even after trekking through a few thousand subway stops, and they're easy to clean.”
Price at time of publish: $150
Size: 5–14 | Materials: Leather, synthetic leather, fabric | Colors: 6 | Heel: 1.75 inches
What We Love: Along with a conventional black hue, Reformation makes these loafers in a variety of spunky colors and patterns.
What We Don’t Love: The style runs large.
Reformation may be best known for their celebrity-loved breezy dresses, but their shoes shouldn’t be slept on, especially the Agathea Chunky Loafer. While the brand offers them in standard black, it’s the sleek, fun-loving patterns that make them extra special. What’s more, true to the brand's sustainable ethos, the loafers are constructed from recouro-regenerated leather — a mix of natural leather fibers, natural latex, and plant materials.
In fact, associate fashion commerce editor, Ruby McAuliffe, applauded the surprising versatility of these edgy shoes after seeing Gigi Hadid sporting them all summer. Comfort is also something you needn’t worry about with this pair because the platform isn’t all that high at 1.4 inches. Plus, the interior cushy padding is the sustainable iteration of EVA foam, meaning your feet won’t be aching after a full day’s wear. For the best fit, opt for a half-size down, as they can be a bit spacious.
Price at time of publish: $268
Size: 5–11 | Materials: Leather welt, rubber, recycled tire rubber chips, sustainable EVA foam, printed hair on cowhide | Colors: 8 | Heel: 1.4 inches
What We Love: The tassel adds a bit of playful flair.
What We Don’t Love: There aren’t options for wide feet.
Known for their craftsmanship and great price tags, Franco Sarto prides themselves on creating elevated classics. In our eyes, the Ballina Tassel Loafer is the star of the loafer show. Available in two unique colorways, slate gray patent leather as well as biscuit brown with a cream upper, along with black, atop a chunky platform and heavily lugged sole, these loafers are a standout. The tassel embellishment also differentiates this pair from others, making for a fun adornment.
Aside from the aesthetic features, these shoes are made of leather and recycled materials, and feature a soft sole for optimal comfort. One downside is that they do require some break in time before they’re fully comfortable to wear — but once broken in, it feels like you’re walking on clouds. We recommend wearing them with a thick sock for short intervals to make the break in process a bit easier.
Price at time of publish: $100
Size: 5–11 | Materials: Leather, fabric, synthetic leather | Colors: 3 | Heel: 1.75 inches
What We Love: Although the heel is pretty high, the robust platform levels out your feet to make walking much more enjoyable.
What We Don’t Love: These can trigger gnarly blisters until they’re properly worn in.
We know what you’re thinking — there’s no way a shoe with such a high heel (4.3 inches to be exact) could possibly be pleasant to wear. Well, being the forward-thinking brand we know and love, Reformation already thought about that and found a solution to a potentially painful problem.
The secret lies in the heightened design: The two-inch platform elevates the balls of your feet so you aren’t standing at such a harsh angle. That, paired with the broad square toe and pillowy soles, make them much more enjoyable to walk in. Keep in mind that the box calf leather upper can feel a bit rigid at first (and may cause friction), but the leather will soften with wear — patience is a virtue here. We advise wearing black tights or socks as a buffer to prevent blisters.
Price at time of publish: $348
Size: 5–11 | Materials: Box calf leather | Colors: 1 | Heel: 4.3 inches
What We Love: Yes, these shoes are incredibly cute, but it’s a bonus that they ship out quickly. (We received ours in just two days.)
What We Don’t Love: The shoes don’t come in half-size options.
InStyle commerce writer Bianca Kratky always relies on & Other Stories to deliver quality, stylish shoes. So, when she decided to dive head first into the chunky loafer trend, ordering from the brand was a no-brainer — and they arrived in two days, to boot. “I love the sleek and shiny finish, and the sturdy body of the shoe,” she says. Emphasis on sturdy: The body and uppers are shaped with staunch leather, and the thick rubber soles can endure heavy stomping.
The sizing, on the other hand, can be a bit iffy. “They don’t offer the shoes in half-size options,” says Kratky. “Because of this, the shoes hurt my feet the first few times I wore them. But after a few weeks, the leather softened and expanded. Now they fit like a glove!”
Price at time of publish: $129
Size: 5–11 | Materials: Leather upper, rubber sole | Colors: 1 | Heel: 2.1 inches
What We Love: Patent leather feels fancier than other materials, but the casual details on these loafers allow you to dress them up or down.
What We Don’t Love: They aren’t as lightweight as other options.
Craving a low-key style with a high gloss finish? Patent leather is the way to go. The shiny, grain-free material looks inherently more elevated than standard leather, yet it’s versatile enough to be worn nearly anywhere, depending on what you wear it with.
When it comes to patent leather loafers, this pair from Proenza Schouler strikes a perfect middle ground between casual and dressy: The easy slip-on style combined with chunky lug platforms and contrast stitching make these ideal for chill coffee dates and in-office days alike. As with many loafers, wearing socks will help break them in. That’s especially the case with this pair as the jagged upper outline can rub against the top of your feet. Once they mold to your shape, it will be smooth sailing.
Price at time of publish: $895
Size: 6–11 | Materials: Leather upper, rubber sole | Colors: 2 | Heel: 1 inch
What We Love: The interior is designed with Madewell’s Cloudlift padding, which really does feel as though you’re walking on a bouncy cloud.
What We Don’t Love: These run slightly large.
Shoe shopping becomes exponentially more frustrating when you have wider feet. On top of ensuring you select the right size (especially if you’re an online shopper), you need to search for designs that aren’t too confined or better yet, flexible — two features that are rather uncommon for loafers. However, Madewell’s Bradley Lug-Sole Loafers are the solution to your cramped-shoe woes. There's ample room in the toe box to comfortably fit wider feet, and with such an abundance of half-size options, you’re sure to find the perfect fit. They do tend to run about a half-size too big, so to be on the safe side, it may be best to choose a half-size down.
Looks wise, they’re thick enough to be on trend, but these are remarkably lightweight, as if there was no chunky sole at all. And with the brand's signature Cloudlift padding, your feet will be cushioned in pure comfort.
Price at time of publish: $158
Size: 5–12 | Materials: Leather upper, recycled rubber sole | Colors: 4 | Heel: 1.75 inches
What We Love: Given their tough indestructible appearance, they're neither weighty nor uncomfortable.
What We Don’t Love: They don’t come in half-size options.
Dr. Martens chunky combat boots are classic in their own right, and these platform loafers are a perfectly balanced hybrid of a contemporary and timeless feel. Marrying the brand’s ’80s grippy rubber outsole style and bright yellow stitching with modern touches, like the double tassel and kiltie fringe, these loafers pay respectful homage to the brand’s alternative heritage.
Even with the 1.5-inch platform, these are unexpectedly lightweight, so it doesn’t feel like your feet are dragging as you down as you buzz around town. Plus, they’re long-lasting: Aside from the Nappa luxe leather (a softer leather that morphs to your feet quicker than other types), these shoes are also weather-repellent, so they’ll withstand rain, mud, and slush. And don’t worry, a quick wipe off with a damp cloth will keep them looking good as new.
Price at time of publish: $170
Size: 5–12 | Materials: Nappa lux leather, PVC, EVA foam, yellow welt fabric | Colors: 1 | Heel: 2 inches
What We Love: The lug-sole does more than just boost traction — it also adds some height and cushioning.
What We Don’t Love: They run a bit big.
A truly modern spin on the classic penny loafer, this time-honored preppy shoe will be on rotation in your year-round wardrobe. The penny loafer style includes traditional elements, including hand-sewn beef roll stitching, which gives the aesthetic slightly more heft, constructed with genuine leather, making it look just as cool with tailored high-waisted chinos as it does with cargo pants. We love to lean into the amazingly preppy vibe and styling them with white, delicate-looking, fold-down socks and a tennis skirt.
Available in three colors — standard black, wine, and trendy, color-blocked black and white — this loafer retains its clean aesthetic, but the thick, toothy sole is a thoroughly modern detail. Despite the bulky underside, these remain featherlight (half a pound to be exact). This virtually guarantees that you won’t feel weighed down after hours of walking.
Price at time of publish: $175
Size: 5–11 | Materials: Leather, EVA foam | Colors: 3 | Heel: 1.1 inches
What We Love: These shoes are produced by hand at the brand’s family-owned factory in Spain.
What We Don’t Love: The fit is very roomy, so those with narrow feet will need to size down.
Purchasing a pair of these embossed Freda Salvador loafers will get you one-of-a-kind, handmade footwear, created in small batch collections. Each shoe is handmade by local artisans at the co-founder’s family-owned factory in Spain, where skilled shoemakers sew and stamp the sustainably-sourced leather elements together.
Part of the brand ethos is ethical production, and to ensure that the leather is both high quality and responsibly sourced, the co-founders have partnered with the Leather Working Group, meaning that each leather shipment came from a certified tannery committed to improving their environmental impact. The result? Truly unique loafers that are made with love.
The Hana loafers blend classic penny loafer with contemporary features for a sensibility that is edgy, elevated, and functional all at once. Constructed from 100 percent Italian leather in black embossed croc with a glossy sheen brings a rich texture to the time-tested penny loafer to create a distinct look that is unexpected in the best way. With a square toe and just the right amount of a chunky rubber sole, the loafer will instantly level up any outfit. For an even more striking look, go for the black and white dotted snake embossed iteration.
“Croc is a neutral in my book, and I’m not embarrassed to admit I wear these loafers with pretty much everything because not only do they go with everything, but they also make my entire outfit look polished and expensive without any of usual penny loafer preppiness,” says Kaitlin Clark, senior beauty commerce editor. “Plus I’m still a total sucker for shiny things."
The brand clearly states that these shoes are spacious, which makes choosing the correct size easier for those with wide feet, but those with slender soles may need to go smaller.
Price at time of publish: $395
Size: 5–11 | Materials: Leather, rubber EVA lug-sole | Colors: 4 | Heel: 1.5 inches
What We Love: You rarely find suede in such a gorgeous light taupe color.
What We Don’t Love: The toe is quite narrow.
If images of plaid skirts, black tights, and cozy knit sweaters immediately flood your mind when you think of loafers, let this style from Bernardo Selma prove that they can be worn year round. Yep, even in warmer weather. This loafer boasts a rainbow of caramel tones, starting from the lighter lug-sole, up to the camel-colored mid-sole, ending at the smooth suede body. These calming hues are a welcome change from the typical black leather loafer, and together, they exude a fresh and lighthearted energy that is right for every season.
Although the chunky stacked heel is higher than most others on our list, they’re a cinch to walk in. However those with wide feet should proceed with caution: You may find it challenging to shimmy into the extra slim shoe.
Price at time of publish: $228
Size: 6–11 | Materials: Suede, leather, rubber | Colors: 5 | Heel: 1.75 inches
What We Love: Because of the open back design, these have a shorter break in period.
What We Don’t Love: They run somewhat small, try going up a half-size.
Mules are everywhere right now and this trendy, fashion-forward chunky iteration is a must-have for every shoe collection. These are similar to the Sam Edelman Laurs Lug-Sole Loafer with one obvious difference: They don’t have a back. It has an open back for easy slip-on and off access, a cushioned insole for comfort, gold-tone metal embellishment on the upper, and a super durable block heel and platform sole.This carefree and casual style is a great option if you’re after that ’90s-inspired vibe.
We know what you’re thinking: A slip-on shoe open heel design must make the shoes less secure. The opposite is in fact true, though. These mules feel sturdy and feet won’t slide around while wearing them (even in humid weather). Swap your sandals for these mules, which are an especially terrific choice to wear between seasons, and pair them with study denim or layered dresses for a moody vibe.
Price at time of publish: $100 (originally $150)
Size: 5–12 | Materials: Leather, synthetic leather | Colors: 3 | Heel: 1.5 inches
What We Love: The traditional penny loafer design gets a major upgrade with the fun color selections.
What We Don’t Love: Like many loafers, they run large.
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. Sure, there may be endless penny loafers to choose from, but this pair from Free People stands out from the rest — and not just because of the color variety, which we must say, is excellent. The true value all comes down to the high quality design of the shoe. They’re made with smooth, buttery leather that quickly morphs to the shape of your foot, and just-chunky-enough lug rubber platforms with thick, dramatic teeth on the sole.
Unlike most of the other options on this list, this traditional penny loafer is available in several spunky colors, like bright turquoise, a more subdued olive, purple-tinged mulberry, and a mauve-blush pink hybrid. So if you’re looking to turn a classic on its head, this is one way to do it.
The one downside is they run a little big (which you’ve probably realized by now is relatively common for this shoe style). Try going down a half-size for the ideal fit.
Price at time of publish: $148
Size: 36–41 | Materials: Leather, rubber | Colors: 7 | Heel: 1.75 inches
Uppers on chunky loafers are commonly made from three different materials: Leather, suede, or synthetic fibers. When it comes to durability, comfort, and lasting appeal, all of our experts endorse purchasing leather loafers. “Real leather forms to the foot over time, making them more comfortable,” explains New York City-based personal stylist Nejla Renee. (Think about your best pair of leather sneakers or boots, for example.)
Similar to leather, suede will also mold to your feet and is relatively dependable. That said, it requires more frequent upkeep and consistent cleaning to maintain, as it’s basically a magnet for picking up both city grime and country dirt. However, with regular brushing and spot treatments with white vinegar when needed, your suede will look fresh. If you fall in love with a stylish pair of suede loafers that are truly excellent for transitioning into fall, like the Bernardo Selma Suede Lug Loafer, the additional care is well worth the effort.
As for synthetic leather, our experts say that aside from being water-resistant, they don’t compare in quality to real leather, and typically, they’re not as comfortable. “Sometimes people opt for synthetic leather thinking it’s more eco-friendly since no animals are harmed in production,” says Renee. “Do your research because a lot of synthetic leather options are made from plastic which end up being worse in the long run.” Still, if you’re on a budget and can’t afford real leather, the Crown Vintage Sage Penny Loafer is an exceptional choice that has a minimal break in time.
Black and brown may be the most popular loafer colors, but some brands offer vibrant shades and patterned iterations. Take the Reformation Agathea Chunky Loafer, for example. The leopard pattern really makes a statement, especially with the upper made of silky printed hair on cowhide, but we’re also swooning over the other variations too, like the patent tortoise, as well as the color-blocked options in nutmeg and white and the more alternative-looking black and white.
Of course, the color you select really comes down to personal preference. If you’re looking for a versatile shoe, stick with a muted hue, like black or brown. “Black goes with everything, while brown can be a nice touch and easily transitions with different looks,” says New York-based image and wardrobe consultant Beverly Osemwenkhae, while Renee adds that metallics (including silver and gold) fall into the neutral category.
On the flip side, professional wardrobe stylist Nicole Muteku suggests going bold with your shoes to “add personality to your look.” For a surprising pop of color, try the Free People Lyra Lug-Sole Loafer in serpent green or bright turquoise.
While all chunky loafers inherently boost height with their thick soles, some have chunky heels to lengthen your legs. According to Osemwenkhae, loafer heels are usually around 1.5 to two inches. That’s not to say they can’t go higher: The heel on the Reformation Lolita Platform Loafer is 4.3 inches tall (although it doesn’t feel it).
When selecting a heel height, consider how much you’ll be walking around in the shoes. The higher the heel, the more risk you take for aching arches. That is, unless you opt for a taller platform to keep your foot balanced at a comfortable angle.
Regardless of your personal style — preppy, goth, edgy, trendy, you name it — chunky loafers can go with pretty much any look. “There are so many ways to play,” says Osemwenkhae. “I love chunky loafers with a slip dress or a micro skirt and oversized sweater, and they also pair well with a relaxed suit.”
To lean into the preppy trend, Muteku recommends pairing loafers with a chic sock for a fun flare. And if you want to keep things casual, Renee suggests styling the shoes with straight-leg jeans and a white T-shirt.
For busier styles, like leopard or color-blocked options, all our experts say to keep the rest of your outfit simple (try a solid colored dress or jeans and a button down) and really let the shoes take center stage. Osemwenkhae also says a monochrome look will highlight an attention-grabbing loafer.
This depends on the material, but for the most part, you can wipe down leather shoes with a damp cloth to buff out scuffs and remove dirt. If your loafers have seen better days and need some extra TLC, take them to a leather repair shop. These experts have tools that will restore the shoes to their glory days.
For suede, we suggest investing in a suede brush to regularly wipe away dirt and grime. The material can also benefit from periodic leather shop visits.
Amanda Rosenthal is a commerce writer for InStyle. With help from InStyle’s commerce editor Mary Honkus, they compiled this list of the best chunky loafers, making selections based on style, quality construction, and versatility. Many of the picks were also tested by members of InStyle’s commerce team. They also interviewed three style experts, New York City-based personal stylist Nejla Renee, New York-based image and wardrobe consultant Beverly Osemwenkhae, and Atlanta-based professional wardrobe stylist Nicole Muteku to learn how to style the best chunky loafers.
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