Slip-On Shoes Guide

June 04, 2020

Slip on and go. 

Aka the beautiful ease and speed that slip-on shoes afford to head out the door. 

While typically thought of as a spring/summer style, with working from home more than ever, they offer us a more professional alternative to slippers and thus help get us in the right state to be more productive year round.

But what slip-on style is right for you?

Below we’ve compiled a comprehensive guide to some of the most popular slip-on styles:



Loafers are the King of slip-on style, offering the casualness of a house slipper with the swag of a dress shoe. In fact, the first loafers were designed for King George VI as a casual house shoe.

While traditionally worn without socks, if you are wearing socks, aim for monochromatic. Match the color of your socks to your jeans or trouser color. It distracts less and allows your loafers to shine more.

• • •


Penny Loafers

Penny loafer takes their name from the 1950’s when college kids would stuff coins/pennies into the visible slit on the strap at the front. While first associated with college prep style, Penny loafers work from laid back looks of athleisure or shorts to dressier looks paired with trousers or suits.

Penny Loafer Sneakers

Horse-Bit Loafers

The Horsebit loafer made its debut in 1953, thanks to Aldo Gucci, the innovative son of company founder, Guccio Gucci. Taking the penny loafer shape and inspired by English racing, Gucci added the horse-bit, the piece of metal that typically fits in a horse's mouth. These loafers became a prominent staple in the 70s and 80s amongst Wall Street. 

We love horse-bit loafers because they look more dapper than your more casual penny loafer. They are more easily dressed up and nicely pair with a well fitted suit.

Horse-Bit Loafer Sneakers


Belgian Loafers

In the 1940s Henri Bendel (the first guy to bring Chanel to the states) designed an understatedly elegant loafer with a small, but unmistakable bow on the front. The slip-ons became a favorite, seen from Madison Avenue to Palm Beach in the ’60s, as comfort and class were the themes of the day. 

We love Belgian loafers for their retro feel. They have just enough flash without distracting from other parts of your outfit.

Belgian Loafer Sneakers

Boat Shoes

Playing off the Penny Loafer and Inspired by Moccasin construction, as their name implies, boat shoes are designed for use on a boat to be water resistant and non-slipping. In 1935, Paul A. Sperry of New Haven, Connecticut noticed his dog's ability to run easily over ice without slipping. The grooves on the paws of his cocker spaniel, Prince, inspired him to try cutting grooved patterns (siping) into a natural rubber sole.

We reserve our boat shoes for the summer, but they work well for a year-round prep style too. Think polos, button ups, trousers, and light colored pants.

Boat Shoe Sneakers


Slip-On Sneakers

Evolving from their loafer predecessors, Slip-on sneakers rose to prominence in the late 70s with the introduction of Vans checkerboard. 

Steve Van Doren, son of Vans founder Paul Van Doren, noticed that teenage skaters were coloring the rubber midsole of their shoe with black pens to create a checkerboard look. Steve then took this pattern in 1977 to the canvas upper of Vans to create the unmistakable look. 

Today that classic silhouette has become the starting point for most slip-on sneaker styles you see today with its rubber sole and elastic inserts.

Slip-On Shoes


Conclusion: What should I buy?

As we love the hybrid shoe/sneaker space, most of the loafer styles above we’ve adapted into sneakers. We find this way you get the timeless dressy look of the loafer with the all day comfort of a sneaker.

Want something dressier? Aim for a Horse-Bit Loafer
→ Recommended: Chancellor Collection Horse-Bit Loafers 

Want a mix between dressy and casual? Aim for a Penny Loafer
→ Recommended: Abe Cognac Plaid Penny Loafers 

Want something casual? Aim for a slip-on sneaker
→ Recommended: Ellison Hand-Painted Cognac Sneakers


View all our slip-on shoes →

Leave a comment

Comments will be approved before showing up.