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How to Wear Mens Leather Loafers

April 02, 2023

Leather loafers for men are a versatile type of mens formal shoes that have become a staple in mens smart casual shoes collection. They are typically slip-on shoes that lack laces or any other fastening mechanism. This makes them easy to put on and take off, which has contributed to their popularity among men of all ages. I often say that they’re basically slippers that I’m allowed to wear outside, and even wear with a suit or a tuxedo!

Loafers are basically the perfect shoe; they can be used in such a range of formalities whilst remaining one of the single most comfortable shoes you can put on your feet. This makes them an absolute must for the modern mans wardrobe, from the beach to the boardroom, loafers are a mans true best friend. Today we are going to get into the weeds on exactly what a loafer is, where they’ve come from, what styles exist, and of course, how they’re made.

HISTORY OF THE LOAFER

The history of loafer’s dates to the early 20th century, when Norwegian farmers wore a similar style of slip-on shoe called the Aurland moccasin. This shoe was designed for practicality and comfort, with a durable leather construction and a simple, functional design.

History of loafers worn by Norwegian farmers in 1900s

Loafer type worn in the 1900s. Picture: fratelliborgioli.com

In the 1930s, American tourists began visiting Norway and bringing back the Aurland moccasin as a souvenir. The shoe soon caught on in the United States, where it was marketed as a fashionable, casual shoe for men. This led to the development of a variety of different styles of loafers, each with their own unique features and characteristics.

During this time, the penny loafer became especially popular among college students. This type of loafer featured a small, diamond-shaped slit on the top of the shoe, which was often used to hold a penny for good luck. This trend caught on quickly, and soon penny loafers were a staple of Ivy League style.

In the 1950s and 1960s, loafers became associated with the "preppy" style that was popular among young men. Celebrities like James Dean and Elvis Presley helped to popularize this look, which often included loafers paired with khakis, blazers, and other classic clothing items. Over time, loafers have remained a popular choice for men's footwear. They have been worn by everyone from business professionals to punk rockers, and they continue to be a versatile and stylish choice for any occasion.

TYPES OF LEATHER LOAFERS

PENNY LOAFERS

The penny loafers is a type of loafer that features a distinctive diamond-shaped apron on the vamp, which is often used to hold a penny for good luck. This type of loafer became popular among Ivy League college students in the 1930s and has remained a staple of classic men's fashion ever since.

Sparrods & Co Martin Penny Loafer in dark brown calf leather

What makes the penny loafer special is its timeless style and versatility. It can be dressed up or down, and it pairs well with everything from khakis and a blazer to jeans and a t-shirt. The slip-on design of the penny loafer also makes it easy to put on and take off, which is a convenient feature for men on the go.

Black loafers for men. Comfortable slip-on shoes

Sparrods & Co - Martin Black Penny Loafers in Calf leather

One of the most famous wearers of the penny loafer was John F. Kennedy. He was often seen wearing a pair of penny loafers with his signature khakis and button-down shirts, which helped to popularize the style even further.

Today, penny loafers are still a popular choice for men leather shoes, especially among those who appreciate classic and timeless style. They can be found in a variety of leather materials and colors, ranging from traditional brown leather loafers to more modern shades like navy blue or tan loafers.

Mens loafers shoes in brown leather worn with suitSparrods & Co Martin Espresso Penny Loafers

Some penny loafers even feature decorative details like contrast stitching or tassels, which add a touch of personality to this already iconic shoe. Whether you're a fan of classic Ivy League style or simply appreciate the timeless elegance of the penny loafer, this type of slip-on shoe is sure to remain a beloved part of men's fashion for years to come.

HOW TO WEAR PENNY LOAFERS

One classic style suggestion for penny loafers is to pair them with khakis or chinos and a button-down shirt for a preppy, Ivy League-inspired look. This outfit is perfect for a casual day at the office, a weekend brunch with friends, or even a dinner date.

For a more modern take on the penny loafer, you can try pairing them with slim-fit jeans and a fitted t-shirt or sweater. This look is both casual and stylish, and it's a great way to show off your love of classic menswear while also staying on-trend.

Mens tan loafers worn with dress pantsSparrods & Co Martin Penny Loafers in Cognac Calf

Finally, for a dressier occasion, you can pair burgundy penny loafers with a suit or blazer. This is a great way to add a touch of personality to an otherwise traditional outfit, and it's sure to make you stand out in a sea of plain black dress shoes.

Mens slip on shoes in burgundy paired with dress pantsSparrods & Co Martin Penny Loafers in Burgundy

Just make sure to choose a pair of penny loafers in a classic, neutral color like brown or black, so that they complement your suit rather than competing with it.

TASSEL LOAFERS

Similar to the penny loafer, a tassel loafers is a slip-on shoe without laces or buckles. However, what sets tassel loafers apart from other loafers is the decorative tassel on the front of the shoe. This style of loafer originated in the 1940s and quickly became popular among Ivy League college students, just like the penny loafer.

Sparrods & Co Tassel Loafer in Black Calf

What makes the tassel loafer special is its sophisticated yet relaxed style. It's a mens leather loafers that can be dressed up or down, making it a versatile choice for any occasion. The tassels on the front add a touch of personality and whimsy, while the overall design is sleek and understated.

Tassel loafers are often associated with traditional and classic menswear. They're a favorite among professionals who work in more conservative industries, like law or finance. However, they're also a popular choice for men who appreciate timeless style and quality craftsmanship.

Mens tassel loafers in tan worn tailored with wedding suit

Sparrods & Co Albert Tassel Loafer in Cognac

Some famous wearers of tassel loafers include style icons like Cary Grant and Paul Newman. These men were known for their impeccable taste and classic sense of style, and the tassel loafer was a natural choice for them. Whether you're a fan of classic menswear or simply appreciate the timeless style of the tassel loafer, this type of shoe is sure to remain a beloved part of men's fashion for years to come.

HOW TO WEAR TASSEL LOAFERS

One classic style suggestion for tassel loafers is to pair them with dress pants and a blazer for a sophisticated, business-casual look. This outfit is perfect for a day at the office or a formal event. For a more casual look, you can pair tassel loafers with slim-fit jeans or khakis and a button-down shirt. This look is both comfortable and stylish, and it's a great way to dress up your casual outfits.

Sparrods & Co Albert Suede Espresso Tassel Loafers

Another fun way to wear tassel loafers is to pair them with no-show socks and shorts for a summery, preppy look. This is a great option for a weekend barbecue or a day out with friends.

Black loafers for men worn without socksSparrods & Co Albert Black Tassel Loafers

Finally, for a dressier occasion, you can pair tassel loafers with a suit or a tuxedo. This is a great way to add a touch of personality to your formal outfit, and it's sure to make you stand out in a sea of plain black dress shoes.

Mens slip on shoes in burgundy worn with socks for the officeSparrods & Co Albert Burgundy Tassel Loafers

Just make sure to choose a pair of tassel loafers in a classic, neutral color like brown or black, so that they complement your suit rather than competing with it.

BIT LOAFER

The bit loafer also known as Gucci Loafer, is another type of loafer that is characterized by a decorative metal bit or strap on the front of the shoe. This distinctive detail was inspired by the equestrian world, where riders would often use metal bits to control their horses. Bit loafers first gained popularity in the 1950s and 1960s and have since become a staple of mens casual leather shoes.

What makes the bit loafer special is its sophisticated and elegant appearance. The metal bit or strap adds a touch of luxury to the shoe, making it a great choice for dressier occasions. However, like the penny loafer, the bit loafer is also versatile and can be dressed up or down depending on the occasion.

The bit loafer is often worn by men who appreciate classic style and elegance. It is a popular choice for business professionals who want to add a touch of personality to their work wardrobe, as well as for grooms and wedding guests who want to look their best on the big day. Celebrities such as Ryan Gosling, Bradley Cooper, and Justin Timberlake have been spotted wearing bit loafers on the red carpet, further cementing their status as a fashionable and sophisticated choice for mens designer loafers.

HOW TO WEAR BIT LOAFER

For bit loafers, a classic style suggestion is to pair them with dress pants and a blazer for a polished and sophisticated look. This combination is perfect for formal events, business meetings, or any occasion that calls for a more dressed-up attire.

Another style suggestion for bit loafers is to pair them with shorts and a casual shirt for a relaxed yet stylish outfit. This look is perfect for a weekend getaway or a day out with friends.

DRIVING SHOE

A driving loafer, also known as moccassins, is a type of loafer that was originally designed for the specific purpose of driving. It features a low profile, slip-on design with a rubberized sole that provides excellent grip on the pedals of a car. Driving loafers typically have a moccasin-style construction with a separate piece of leather or suede that wraps around the heel of the shoe, providing additional support and structure.

Driving Shoes also known as moccassinsSparrods & Co Moccassins in navy blue calf leather

What makes driving loafers special is their combination of form and function. They were designed to be practical and comfortable for driving, but they also have a sleek, stylish appearance that makes them a popular choice for everyday wear. Many driving loafers feature decorative elements such as tassels, contrast stitching, or metal bits, which add a touch of personality and elegance to the shoe.

Driving shoes in burgundy. Best moccasins for men.Sparrods & Co driving shoes in burgundy leather

Driving loafers are worn by a wide range of people, from car enthusiasts and racing drivers to fashion-conscious men and women. They are especially popular among those who appreciate the classic, timeless style of the shoe and the comfort and practicality it provides.

Overall, driving loafers are a unique and practical shoe that combines form and function with style and elegance. Whether you're a car enthusiast or simply appreciate the classic look of a well-made loafer, a pair of driving loafers is sure to make a stylish and practical addition to your shoe collection.

HOW TO WEAR DRIVING LOAFERS

To style driving loafers, you can take inspiration from their sporty and casual nature. They are great for a laid-back weekend look or a casual day at the office. Pair them with tailored shorts and a polo shirt or a linen button-down shirt for a relaxed yet refined outfit. They also pair well with chinos or slim-fit jeans and a lightweight sweater or a casual shirt.

For a more dressed-up look, you can wear them with a blazer or sport coat and tailored pants. Keep in mind that driving loafers are typically designed with a more rounded toe and a shorter vamp, so it's best to avoid wearing them with formal suits or dress pants.

BOAT SHOE

A boat shoe, also known as a deck shoe, is a type of loafer originally designed for sailors and boaters. They were first introduced by the Sperry Top-Sider company in 1935 and have since become a popular style for both men and women. Boat shoes are typically made from leather or canvas and feature a non-slip rubber sole with grooves or sipping that helps to provide traction on wet surfaces. One of the most distinctive features of boat shoes is their lace-up design with leather laces that run through metal eyelets, allowing the shoes to be adjusted for a comfortable, snug fit.

Boat shoes are designed to be worn without socks, and their breathable construction helps to keep the feet cool and comfortable in warm weather. They are also often treated with water-resistant coatings, making them ideal for wearing on boats or around water.

Boat shoes are popular among people of all ages, but they are particularly favored by those who appreciate classic, preppy styles. They are often associated with coastal living and outdoor activities, but can be worn by anyone looking for a comfortable and stylish shoe that can be worn in a variety of settings.

HOW TO WEAR BOAT SHOES

To style boat shoes, a classic look is to pair them with shorts or rolled-up chinos and a polo shirt. This look is perfect for a casual day out or a summer barbecue. Boat shoes can also be worn with jeans and a casual shirt for a relaxed yet stylish outfit.

For a preppy twist, you can wear boat shoes with a pair of colored chinos or shorts and a button-down shirt with a sweater tied around your shoulders. This outfit is perfect for a day out on a boat or a weekend brunch with friends.

To dress up boat shoes, you can wear them with a blazer or a sports jacket, a crisp dress shirt, and a pair of slim-fit trousers. This look is perfect for a semi-formal event or a business casual setting. Make sure to choose a pair of boat shoes in a classic color like navy or tan, and avoid wearing them with formal suits.

Jessup Says

Loafers have become an essential part of men's footwear due to their versatility, comfort, and ease of use. With their slip-on design and lack of laces, they offer a unique combination of practicality and style, making them suitable for a wide range of occasions, from casual outings to formal events. Whether you prefer a classic penny loafer, a modern driving loafer, or any other style, loafers are sure to add a touch of sophistication and comfort to your wardrobe.


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