8 Most Comfortable Loafers for Men – Relaxing Style For 2023

The OG lounging shoe, the loafer is an integral part of any successful footwear collection. Smarter than a slipper yet equally as kind to your trotters, it’s the perfect choice for office days, date nights, weddings, and more.

But with so many brands offering up their own version, finding the perfect pair can be easier said than done. To help, I’ve pulled together the most comfortable loafers for men. These are the options that not only ensure you look your best, but help keep your feet happier than a pig in shit.

What are you waiting for? Keep reading for my rundown of the loveliest loafers around.

Key Takeaways

If you’re looking for a more comfortable (yet equally stylish) alternative to your dress shoes, investing in a pair of loafers is the shrewdest sartorial move you could make.

From tasseled versions to summer essentials, I’ve curated a list of the most comfortable loafers for men by poring over dozens and dozens of sites and reviews. You’re going to find a range of options, including my favorite from G.H. Bass & Co and Vostey’s wallet-friendly version.

Why it’s great: This is G.H. Bass & Co’s iconic penny loafer with a twist. Updated with a chunky EVA outsole, it’s a modern and lightweight shoe that provides all-day comfort whether you’re in the city or sipping beers at your go-to spot. The soft yet sturdy leather will get softer with time and mold to the shape of your foot for ultimate satisfaction.

How to wear it: The world is your oyster, my friend. You can show these off just about anywhere (and I’m sure you’ll want to). Dress them up with a jacket, plain tee, and slacks, or keep it chill with your favorite denim and flannel shirt.

Flaws but not dealbreakers: Customers say the Weejun 90 Larson runs slightly large. If you’re in-between sizes, they recommend choosing half a size smaller.

Material: 100% Leather | Sizes Available: 6-13 | Colors: 1 | Style: Penny Loafers

Why it’s great: Whether you’re dining al fresco or spending your summer in the city, these Vostey loafers will ensure you look the part. But they’re not just a pretty face. Thanks to the latex cushioned footbed and foam cushion insole, you never have to worry about sore feet.

How to wear it: You can wear them with a range of pants, but I think they look best with shorts or khakis. Complete the outfit with a fine knit sweater and roll up the sleeves slightly for a touch of nonchalant style.

Flaws but not dealbreakers: I’m marking them down for the synthetic material, but this does make them considerably cheaper than the other versions on this list.

Material: 100% Synthetic | Sizes Available: 7-13 | Colors: 3 | Style: Driving Shoes

Why it’s great: Presented in elegant grain leather, these beauties will bring a luxurious touch to formal and smart-casual outfits alike. But why are they one of the most comfortable loafers for men? They’ve been skilfully hand-welted to make them lighter, more flexible, and softer on the feet.

How to wear it: You can wear them with the usual suspects (slacks, shirts, suits) but I think they look particularly great when they’re given a preppy twist. Achieve an Ivy League-inspired fit with an Oxford shirt and khakis, complete with a tied sweater worn on your shoulders.

Flaws but not dealbreakers: Sizes sell out quick but you can still make an order. You may just need to wait a few more weeks for delivery.

Material: 100% Leather | Sizes Available: 8-13 | Colors: 1 | Style: Penny Loafers

Why it’s great: Lined in smooth leather and featuring durable anti-slip rubber soles, these loafers are the perfect everyday companion. They’ll make sure your feet are happy, while offering unbeatable style that looks as good with tailoring as it does with your favorite smart-casual separates.

How to wear it: Thanks to their semi-smart style, you can wear Aurelien’s loafers with just about anything. My go-to combination is a pair of slim-fitting slacks, a plain crew neck T-shirt, and a suede bomber jacket.

Flaws but not dealbreakers: Seeing as they’re suede, you’ll need to make sure they’re generously protected if you want to wear them during the fall or winter.

Material: 100% Suede | Sizes Available: 6-14 | Colors: 16 | Style: Slip-on Loafers

Why it’s great: When it comes to dressing smartly, you naturally turn to dress shoes. However, these Myrqvist loafers are a far more comfortable alternative. The full leather construction gets softer as time passes, while the sleek silhouette makes them perfect for formal events such as weddings and work conferences.

How to wear it: For ultimate smartness, team yours with tailoring. For something a little more relaxed, choose a pair of slim-fitting jeans and pair them with a casual shirt.

Flaws but not dealbreakers: They’re not the softest option I found, but as far as formal footwear goes, they’re pretty damn comfortable.

Material: 100% Leather | Sizes Available: 5.5-13 | Colors: 2 | Style: Penny Loafers

Why it’s great: Tassel loafers, like this pair from Velasca, have always been a consistently cool shoe, and perhaps one of the most versatile items you can own. Made from suede calf leather, the Beltramm is comfortable, hardwearing, and seriously stylish. A must-have for every collection.

How to wear it: The opportunities are aplenty. Dress these up with a navy suit and crisp white shirt, or keep it casual with a button-down shirt and khakis. Wearing socks is optional, but I’d suggest an invisible pair if that’s the look you’re after.

Flaws but not dealbreakers: The calf leather lining may feel a little stiff at first, but they’ll get more comfortable after every wear.

Material: 100% Suede | Sizes Available: 5-14 | Colors: 2 | Style: Tassel Loafers

Why it’s great: Since first gaining popularity in the 1930s—when it was introduced by shoemaker George Bass—the penny loafer has become a mainstay in any well-dressed guy’s wardrobe. This version from Oliver Cabell is an excellent summer option, providing all-day comfort (thanks to the micro foam footbed) and timeless style that’ll take you from city vacations to weekend drinks with friends.

How to wear it: Keep your pants slim (potentially rolled) and find your favorite button-down Oxford (I find a subtle stripe works best). For an extra layer, you may want to consider a classic Harrington or denim jacket.

Flaws but not dealbreakers: The suede construction restricts them somewhat (beware of the rain), unless you have some spray protector to hand.

Material: 100% Suede | Sizes Available: 6-15 | Colors: 1 | Style: Penny Loafers

Why it’s great: Cole Haan has done everything in its power to make these loafers as comfortable as they are stylish. And it’s worked. There’s leather sock lining and responsive cushioning for softness, plus a perforated footbed to allow your feet to breathe. The low stacked heel ensures ultimate stability.

How to wear it: The penny loafer style is a versatile option that can be dressed up or down. For a smarter ensemble, try them with slacks and a knitted polo shirt. If you’re going down the smart-casual route, I suggest slim jeans and an Oxford shirt.

Flaws but not dealbreakers: Although they are available in a wider fit, they do tend to feel a bit more narrow than your average loafer. Bear this in mind if you usually have issues squeezing your feet into shoes.

Material: 100% Leather | Sizes Available: 6-16 | Colors: 2 | Style: Penny Loafers

Buying Considerations for The Most Comfortable Loafers 

Fit

As with any type of shoe, the fit of your loafers is crucial for comfort. Make sure the loafers are the right size for your feet. They should neither be too tight nor too loose, whether you’re wearing socks or not. Ensure that there is enough room for your toes to move comfortably, and the heel doesn’t slip out while walking.

Cushioning

Look for loafers with adequate cushioning and arch support (if required). Padded insoles, memory foam, or gel inserts can provide extra comfort. Arch support is essential for proper alignment and to prevent discomfort during prolonged wear.

Material

High-quality materials like leather or suede can offer both comfort and durability. You’ll also want to check the stitching and overall construction to ensure the loafers are well-made. A flexible outsole that allows natural movement is also important for comfort during walking.

Why You Should Trust Us

As an experienced fashion writer, it’s my passion to find the best of the best. On top of that, if my love for loafers isn’t enough, would it put your mind at ease if I told you I spent days hunting down the very best pairs? Not settling for mediocre, I’ve made my way through endless options (plus heaps of reviews) to ensure I only share the most comfortable loafers for men.

Final Verdict 

Turns out there are some pretty awesome options out there when it comes to the most comfortable loafers for men. By carefully considering factors such as fit, cushioning, support, material quality, and construction, I’ve found a range of seriously comfy shoes that will soon become a mainstay in your footwear rotation.

G.H. Bass & Co’s Weejun 90 Larson loafers are the ultimate all-rounder. Not too smart or casual, they’re the perfect addition to your everyday wardrobe. Modern, lightweight, and comfortable, you can wear yours at the weekend or show them off at work. Better yet, they’ll get softer with time—so the best is yet to come.