The 29 Best Loafers to Wear With Everything, All the Time (2024)

Table of Contents
Best Overall Loafers Best Horse-Bit Loafers Best Western-Inspired Loafers Best Affordable Tassel Loafers Best Penny Loafers Best Unique Loafers best comfortable loafers Best Designer Penny Loafers Best Everyday Loafers best subtle loafers G.H. Bass Logan Flat Strap Weejuns G.H. Bass Logan Flat Strap Weejuns Gucci Jordaan Leather Loafer Gucci Jordaan Leather Loafer Tecovas The Monterrey Loafer Tecovas The Monterrey Loafer Cole Haan Pinch Tassel Loafer Cole Haan Pinch Tassel Loafer To Boot New York Berle Leather Penny Loafers To Boot New York Berle Leather Penny Loafers Taft Fitz Loafers Taft Fitz Loafers Camper Walden Loafers Camper Walden Loafers Polo Ralph Lauren Edric Leather Penny Loafer Polo Ralph Lauren Edric Leather Penny Loafer Dr Martens Adrian Snaffle Smooth Leather Kiltie Loafers Dr Martens Adrian Snaffle Smooth Leather Kiltie Loafers Paraboot Coraux Loafer Paraboot Coraux Loafer J.M. Weston 180 Penny Loafer J.M. Weston 180 Penny Loafer Blackstock & Weber The Ellis Penny Loafer Blackstock & Weber The Ellis Penny Loafer Ferragamo Penny Loafer Ferragamo Penny Loafer Astorflex Patnoflex Astorflex Patnoflex Dockers Colleague Dress Penny Loafer Dockers Colleague Dress Penny Loafer Banana Republic Amir Penny Loafer Banana Republic Amir Penny Loafer Clarks Tilden Free Loafer Clarks Tilden Free Loafer Bottega Veneta Lug Loafer Bottega Veneta Lug Loafer Brunello Cucinelli Leather Tassel Loafers Brunello Cucinelli Leather Tassel Loafers Magnanni Rafa II Apron Toe Bit Loafer Magnanni Rafa II Apron Toe Bit Loafer FAQs References

Not toot our own horn or anything, but when it comes to loafers, Esquire has a pretty decent reputation. The modern iteration that we know and love (not to be confused with the moccasin, which Native Americans originated) was first popularized by our editors back in the ’30s. So when it comes to the best loafers, rest assured that we know what we’re talking about.

The most important thing to consider is the variety. The ubiquitous loafer takes on many forms and names: penny, dinner slipper, driver, and Venetian are just a few. What ties them all together is that they are slip-on, no-fuss shoes intended for easy living and, well, loafing around in style. co*cktail party on the horizon? The classic Gucci horse-bit is right up your alley. Looking to cruise down Big Sur or the Amalfi Coast? The dependable Ferragamos are best for that. Want to channel the vibe of a ’30s Esquire editor? The OG loafer, the G.H. Bass Weejun, is what you need.

Now that we're tumbling into autumn, the tried-and-true loafer is more than ready to alternate wears with your winter boots. More than a few Esquire editors have been rocking loafers all season around the office. If you want to do the same, take a gander at the selection below. Buy two, three—hell, get one for every day of the week. Look for something classy and stylish, something that'll go with your wardrobe, whether that consists more of blazers or biker jackets. The loafer has been riding strong for nearly a century and will never go out style. And we here at Esquire called it from the very beginning.

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Best Overall Loafers

G.H. Bass Logan Flat Strap Weejuns

The 29 Best Loafers to Wear With Everything, All the Time (11)

Best Overall Loafers

G.H. Bass Logan Flat Strap Weejuns

The OG of loafer manufacturers is still going strong. These are timeless and infallible, with a traditional look that, quite frankly, never goes out of style.

Best Horse-Bit Loafers

Gucci Jordaan Leather Loafer

The 29 Best Loafers to Wear With Everything, All the Time (12)

Best Horse-Bit Loafers

Gucci Jordaan Leather Loafer

Horse-bit loafers are now a dime a dozen, but it all started with this guy right here. Gucci's quality craftsmanship, burnished look, and chic elegance make this pair stand out from the crowd.

Best Western-Inspired Loafers

Tecovas The Monterrey Loafer

The 29 Best Loafers to Wear With Everything, All the Time (13)

Best Western-Inspired Loafers

Tecovas The Monterrey Loafer

Tecovas, purveyor of some of the best Western-inspired styles, also has a nifty loafer that takes after one of our favorite cowboy boots on the market.

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Best Affordable Tassel Loafers

Cole Haan Pinch Tassel Loafer

The 29 Best Loafers to Wear With Everything, All the Time (14)

The 29 Best Loafers to Wear With Everything, All the Time (15)

Best Affordable Tassel Loafers

Cole Haan Pinch Tassel Loafer

Now 49% Off

Tasseled-up and hassle-free: a win-win. Cole Haan does comfort and affordability with everyday ease.

Best Penny Loafers

To Boot New York Berle Leather Penny Loafers

The 29 Best Loafers to Wear With Everything, All the Time (16)

Best Penny Loafers

To Boot New York Berle Leather Penny Loafers

Now 30% Off

From James Dean to Pharrell Williams, the timeless black penny loafer has graced the feet of the best of the best. To Boot's option is sturdy and versatile, whether you want to dress it up for the office or down for the weekend.

Best Unique Loafers

Taft Fitz Loafers

The 29 Best Loafers to Wear With Everything, All the Time (17)

Best Unique Loafers

Taft Fitz Loafers

If you want to look classy without conforming, opt for a fun, bold loafer. Taft has a wide variety of designs, like this dragonfly jacquard weave that puts a little extra something in your step.

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best comfortable loafers

Camper Walden Loafers

The 29 Best Loafers to Wear With Everything, All the Time (18)

best comfortable loafers

Camper Walden Loafers

Camper keeps it classy, cool, and comfy. With a lightweight sole and cushioned footbed, this is a loafer you don't have to be afraid of walking around all day in. Plus, with its contemporary look, you can pair it with just about anything, from jeans to dress pants.

Best Designer Penny Loafers

Polo Ralph Lauren Edric Leather Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (19)

Best Designer Penny Loafers

Polo Ralph Lauren Edric Leather Penny Loafer

These are a bit simple, a bit rugged, a bit classic. With contrast stitching and a sleek, simple silhouette, the minimalist chicness PRL is known for hits the bullseye with these.

Best Everyday Loafers

Dr Martens Adrian Snaffle Smooth Leather Kiltie Loafers

The 29 Best Loafers to Wear With Everything, All the Time (20)

Best Everyday Loafers

Dr Martens Adrian Snaffle Smooth Leather Kiltie Loafers

Dr Martens are perhaps one of the most versatile loafers out there; wear with jeans, work trousers, anything. They'll last you forever, too.

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best subtle loafers

Paraboot Coraux Loafer

The 29 Best Loafers to Wear With Everything, All the Time (21)

best subtle loafers

Paraboot Coraux Loafer

With sewn-through stitching and a simple saddle strap, these elegant loafers are the epitome of understated luxury.

Best Iconic Penny Loafers

J.M. Weston 180 Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (22)

Best Iconic Penny Loafers

J.M. Weston 180 Penny Loafer

Ever wonder who started white socks with loafers? It was J.M. Weston, with this iconic shoe. Safe to say: a white sock will look best with these.

Best Animal-Print Loafers

Blackstock & Weber The Ellis Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (23)

Best Animal-Print Loafers

Blackstock & Weber The Ellis Penny Loafer

Talk a walk on the wild side. (Yeah, I said it.)

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best high-end comfort loafers

Ferragamo Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (24)

best high-end comfort loafers

Ferragamo Penny Loafer

Take it from me (or, rather, my father, who has been wearing high-end loafers for decades; hi, dad!)—in the world of luxury designers, Ferragamo is the most comfortable shoe you’ll come across. It’s pretty chic, too.

Best Versatile Loafers

Astorflex Patnoflex

The 29 Best Loafers to Wear With Everything, All the Time (25)

Best Versatile Loafers

Astorflex Patnoflex

A style so beloved by one Esquire staffer, that he wrote a whole damn review on it.

best affordable everyday loafers

Dockers Colleague Dress Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (26)

The 29 Best Loafers to Wear With Everything, All the Time (27)

best affordable everyday loafers

Dockers Colleague Dress Penny Loafer

Now 29% Off

For affordable—yet classy—loafers, Dockers has you covered. These are under 50 bucks, but they look like they cost five times that much.

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best simple loafers

Banana Republic Amir Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (28)

best simple loafers

Banana Republic Amir Penny Loafer

A solid, classic, infallible penny loafer that looks smart as hell with some white socks.

best affordable comfort loafers

Clarks Tilden Free Loafer

The 29 Best Loafers to Wear With Everything, All the Time (29)

The 29 Best Loafers to Wear With Everything, All the Time (30)

best affordable comfort loafers

Clarks Tilden Free Loafer

Now 52% Off

Clarks are known for their comfort, and these loafers are no different. It'll feel like you're wearing your favorite sneaker, but you'll look like a million bucks.

best chunky loafers

Bottega Veneta Lug Loafer

The 29 Best Loafers to Wear With Everything, All the Time (31)

best chunky loafers

Bottega Veneta Lug Loafer

Why not make a statement? Bottega's chunky, lug-sole loafers are classy and cool, whether you pair 'em with jeans or dress pants.

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best luxury loafers

Brunello Cucinelli Leather Tassel Loafers

The 29 Best Loafers to Wear With Everything, All the Time (32)

best luxury loafers

Brunello Cucinelli Leather Tassel Loafers

Now 40% Off

Crafted from fine leather with Brunello Cucinelli's expert hand, these rich brown loafers are elegant AF.

best elevated loafers

Magnanni Rafa II Apron Toe Bit Loafer

The 29 Best Loafers to Wear With Everything, All the Time (33)

best elevated loafers

Magnanni Rafa II Apron Toe Bit Loafer

For a classic, black loafer that dresses up any look, Magnanni has a comfortable and chic option that makes even jeans look suave.

The 29 Best Loafers to Wear With Everything, All the Time (2024)

FAQs

What color of loafers go with everything? ›

As we know black is a classic and neutral color that can complement a variety of outfits. That is why black penny loafers are suitable for both formal and casual occasions. The sleek and sophisticated design of penny loafers adds a touch of elegance to your overall look.

What are the most versatile loafers? ›

You can see how well a penny loafer mixes with casual clothing such as jeans or a polo shirt, as well as business casual outfits that include odd pants and jackets. Really, the penny loafer is one of the most versatile loafer styles you can own.

Are loafers still in style in 2024? ›

The Elvie Loafers are the epitome of understated elegance, perfect for those who appreciate timeless style and comfortable footwear. We have seen that stylish loafers for women are here to stay in 2024 and beyond. They offer endless styling possibilities and are paired with everything from trousers to skirts.

What is the most versatile color for suede loafers? ›

Which is the Most Versatile Loafer Color? Brown is your best bet if versatility is what you're aiming for. A medium shade of brown specifically can transition smoothly from day to night, from casual outings to business meetings. Pair them with jeans, chinos, or even suits - brown loafers seldom disappoint.

What are three shoe colors everyone must have? ›

The Basics: Black, Beige, and Grey

Let's start with these neutrals. Black, beige, and grey shoes go with anything. Since they are all neutrals, you can wear these colors to offset a more vibrant outfit. Of course, with these neutrals, you can either mix and match or keep them in a similar tonal family.

What color shoe is most versatile? ›

Black shoes are the ultimate wardrobe staple. Known for their versatility, they seamlessly transition from formal events to casual outings. They have the unique ability to elevate an outfit, adding a touch of sophistication and elegance. Moreover, black shoes are the go-to for creating a sleek, polished look.

Which brand has the best loafers? ›

  • G.H. Bass. ...
  • Gucci. From the coveted handbags to those logo-tastic belts, there are so many reasons to love Gucci. ...
  • Tod's. Here's a brand who's history goes back to the early 1920s. ...
  • Church's. There aren't many brands that can say that their origin story begins in the 1600s, except for Church's. ...
  • Grenson. ...
  • Hereu. ...
  • Aeyde. ...
  • Loro Piana.
Feb 7, 2024

Should you wear socks with loafers? ›

Regardless of the climate and temperature, it is always more comfortable to wear a pair of socks with your loafers to avoid sweat and discomfort. This protection between your skin and the leather of the shoe allows you to be comfortable all day long.

Can I wear loafers with everything? ›

Force Them into Every Outfit: While loafers are versatile, they might not suit every ensemble. For example, they may not always pair well with very formal gowns or certain types of sportswear. Wear Ill-fitted Pants: Avoid wearing trousers that are too long or too baggy, which can hide or overshadow the loafers.

What jeans go with loafers? ›

Choose the Right Fit: Ensure your jeans fit well – not too loose or too tight. A slim or straight-leg cut often works best with loafers, creating a clean, streamlined look.

Are loafers good walking shoes? ›

Loafers and Flats

Loafers and flats have to be the second most comfy shoe for walking all day. Loafers offer just enough support in the heel, are light as a feather and give you a breathable, flexible top in the ankle region if you so desire.

Are loafers classy? ›

Despite its simple style, the loafer is a classy item, perfect for dressing up an outfit. Moreover, loafers can be worn for both casual and formal occasions, which makes them extremely versatile .

What to pair with loafers? ›

Loafers are versatile dress shoes that you can dress up or down. They pair well with jeans, chinos, shorts, and shirts or T-shirts for everyday outings.

Should you put shoe trees in suede loafers? ›

If you have a thin, suede driving loafer you don't want to stretch it out at all with an improperly sized shoe tree. Using the correct size will ensure your shoes won't stretch and will be at their best.

How do you wear elegant loafers? ›

For a casual look, pair your shoes with denim shorts and a cotton t-shirt. For a dressier silhouette, wear them with a chino and a linen shirt. Beige, white, light blue... Opt for fresh shades that will blend elegantly with all your summer outfits.

Which color loafers are best for all dress? ›

Purchase a brown, black, or beige pair, and you'll find you can essentially wear them with any ensemble, no matter the cut of your hem, the color scheme of your overall look, or the level of formality.

Are white loafers versatile? ›

Without a doubt, loafers in timeless colours like black and white take the top spot in terms of wearability and versatility. They are failsafe colours that will match effortlessly with any outfit and are perfect for any occasion.

Is it better to wear brown loafers with socks or without? ›

Wear Dress Socks for Style & Comfort

If you want to wear brown loafers without socks, go for them. But if you're looking for a way to keep your feet from sweating or want to give them an extra layer of protection against the elements, there are other options. Ankle socks come in all kinds of styles.

References

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