How to Buy Loafers

Patrick S.
advo
Published in
6 min readJul 2, 2017
Loaf-ers.

This is a guide for the frugal among us. I am by no means an expert on buying high quality bespoke leather shoes, although with time and better money management (we are named after avocado toast after all…) I will hopefully break into that.

What follows is — I hope — a simple guide for buying loafers for the casual beginner.

Loafers are excellent shoes because they are extremely versatile. They can be dressed-up or dressed-down, and easily integrate into whatever style that you fancy. Their comfortable ride, breathability, and ability to be resoled make them a great choice for whatever style/look you’re going for.

Everything from the ubiquitous hipster look:

To the preppy:

To the formal:

To the downright casual:

Whatever your need, loafers are a great shoe for just about any occasion.

Personally, I like to use loafers as my casual on-the-town shoes since they are so versatile and so durable. My favorite shop for reasonably priced loafers is G.H. Bass. G.H. Bass has been making “Weejuns”, the true original penny loafer, since time immemorial, and their quality is an excellent steal for their price. They have something for all budgets with options from their Factory Store to some more premium items in the main site store; personally, I prefer the Factory. Whereever you decide to utlimately buy your shoes make sure to check whether they have factory options, they’re usually cheaper and not that far-off in terms of quality.

Now to get into the shoes, I’ve provided two below that I personally own and can vouch for, and a couple that I’m hoping to pick up soon. These are both in the standard penny loafer style, with a diamond-slit where children used to store actual pennies.

Wilton Weejuns, standard penny loafer style. Note the slit on the top of the shoe — this is where people would store pennies. Hence the name, penny loafer.

The Wilton’s are an excellent casual shoe that have a thin sole for a low-riding profile akin to that of Sperry’s. The tradeoff with the lower sole profile is that although they break in much easier, they do wear out faster. These are great for doing just about anything, and pair wonderfully with a casual blazer look.

Next up, we have The Larson’s. The Larson’s have a thicker sole and are a bit stiffer than the Wiltons. They strike a more formal pose and can be dressed up. Depending on your work place’s dress code rules they’re an excellent every day shoe and have long range in business-casual environments. Depending on the color, you can even wear them with a suit.

Even though G.H. Bass offers great shoes at a reasonable price, there are sometimes situations where you need something a bit nicer. Very formal occasions, or formal offices, may necessitate a step-up. If you’re farther ahead in life, you may want to take a look at the offerings from Allen Edmonds. A&E are classic shoe crafters, and their quality is among the highest. They have an extremely long shelf-life, and more often than not a single pair can run you for life. If you’re looking to spend a bit more, there is no better option.

There are other types of penny loafers as well, including drivers and tassel-loafer iterations.

Jack Erwin makes some really great and long-lasting driver loafers, the Parker’s are my go-to for most things, including driving. The term “driver” came from the fact that the little feet on the bottom of the shoe coupled with its sometimes-vulcanized rubber heel was designed to give the user maximum control over driving a car — whilst allowing their “real” shoes to rest elsewhere in the car. These days there is no longer a delineation between shoes-for-the-car and shoes-for-everything-else.

Jack Erwin driver loafers. Note the little “feet”.

Cole Haan has a very formal tassel style loafer for sale. It’s a bit pricey so check back regularly to see when it comes on-sale. You can also use the Honey Chrome Plug-in to automatically find a better coupon code to add to your cart to discount your purchase!

Cole Haan tassel-loafers. Note the tassels.

The beauty of all the loafers mentioned above is that they can be *re-soled*. They all have leather bottoms except for the drivers. What that essentially means is that as the shoes wear out, holes may appear as time goes on. You can take any of these shoes to a cobbler who will repair the shoes for you, and extend their lifespan. This is an especially great practice because it spreads the dollar cost of your shoe’s life over time — one of the many key strengths of penny loafers.

When to buy?

As for when to buy loafers, no time is more perfect than the present. However, as with all brands, buying off-season is your best bet for finding great deals. Since the Christmas Season is the high point for most retail, look to buy in the post-Christmas doldrums of January to get the clearance level prices as retailers look to clear their inventory and restock for the new season. The second best time is at the end of summer, before the fall items come rolling in — as that is another window when most purchases are made. To really save money, buy winter related items during the summer, and vice versa. Buy one season behind as well (so if it’s the 2018 catalog, look for the 2017 offerings). Compare prices across major vendors, and look at the other sellers on Amazon as well. Between these shopping strategies, you’ll be able to find the perfect loafer for your needs — at the perfect price.

Are you a fan of penny loafers? How do you like to style your shoes? Let us know in the comments section below! If you have any other brands to recommend let me know as well, as I’m always looking for deals, because let’s face it, adulting is hard and things are expensive.

That’s why we created Advo, our new publication focused around everything our parents were supposed to teach us but never did. For more articles like this, and to learn how to even better budget, click the 💚 and link below!

Need to earn some bread for some loafers? See our guide to saving:

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