Wearing Loafers

A lot of men don’t even consider wearing loafers. They can easily look like frumpy old man shoes, finance bro shoes, dainty slippers or sometimes, somehow, all three at once.

If you’re just trying to get dressed like a regular person in the morning, and you don’t want to stand out too much, then you likely stick to more conventional sneakers, or a comfortable dress shoe if your style leans that way. 

We wanted to talk about loafers because they can be incredibly useful in your wardrobe. In terms of formality, they sit somewhere between casual and formal. They are more formal than a sneaker, and less than the typical oxford or derby shoe that you would wear to work or a wedding. By holding this middle ground, they can be paired with a wide range of outfits. You can use them to subtly dress up an otherwise casual outfit and instantly you’re better dressed than 90 percent of the guys in the room. By choosing the right shape, material and design you can avoid the undesirable associations. 

I own two pairs of loafers and I wear them both regularly. In this post, I’ll outline what I like and how I wear each of them. Standard disclaimer applies: this is not a prescription for how you should wear loafers. As you read the remainder of this post, consider if any of the elements discussed apply to your style and wardrobe. If you wear loafers in a different way feel free to share in the comments. 

John Varvatos penny loafers

These were the first pair of loafers I ever wore, and I bought them on Ebay for 25 dollars. At the time, I was looking for a way to try out the style without investing a lot of money. A great way to do this is to buy used or vintage. There is actually quite a lot to say about buying vintage as a way to try things and learn about your style, but we’ll save that deep dive for another post. 

The loafers are mid/dark brown suede penny loafers, with a round versus pointed toe, modest heel and a flat apron. Vertically, the toe is square instead of sloped like more formal loafers.

All of these characteristics combine to make this a more casual pair of shoes. They each represent a move toward the casual end of the spectrum. 

The blunt, square shape does a lot to avoid the appearance of daintiness and formality. 

The suede is also a casual material. Think of leather bomber or biker jackets. They tend to be quite striking and can easily look like costume because of the distinctive design and cultural associations. In suede however, these jackets lose quite a bit of their edge, and look much less dated. It’s the same thing with the loafers. It takes a shoe with a lot of baggage and makes it easier to wear. 

Finally, this is a penny loafer. It doesn’t include the obvious decorative elements of a tassel or snaffle loafer which I find a bit silly, and can definitely carry old man associations. 

These shoes have worked out incredibly well, a pleasant surprise given that I didn’t know anything about loafers when I bought them. I almost always wear jeans. When I’m not wearing jeans, it’s either corduroy or chinos in a casual style. These shoes are therefore more formal than my pants, but only slightly. 

This is perfect for me. I like to dress up my casual outfit with a slightly more formal shoe. But the only way this works is if the difference in formality is not too great. If the loafers were more formal, with a slimmer silhouette or more polished leather, they would stand out and look out of place. These blend in and subtly give the impression of a more considered and smart outfit.

G.H. Bass Weejun 

These loafers share many design elements with the Varvatos pair, including the square shape and matte leather. They are not suede, but with a suede-like finish on the apron and a textured matte leather on the rest of the shoe, the effect is similar.

In contrast to the Varvatos, they have a larger, chunkier lug sole. This is more of a fashion element that I’ve seen people wearing in the last year. I like that it adds a little bit of volume to the shoe, making them easier to wear with slightly wider leg or cropped pants. The risk with choosing more of a fashion element is that you get tired of the look, or that it quickly becomes dated. We’ll see if that effects their longevity and versatility but so far they’ve been fun to wear and it hasn’t been a problem.

I like black because I think the starkness and minimalism of the colour fits into my smart casual style. It can be challenging to incorporate black into a wardrobe because it’s such a stark colour and can be hard to pair with the rest of an outfit, but it is easier with shoes (and perhaps a belt) as they take up less visual realestate than a shirt or jacket. 

The Weejuns stand out a bit more than the Varvatos pair. It’s more likely that someone comments on them. This is neither a good nor bad thing. I tend to wear the Weejuns when I want my look to be just a little bit more striking.

If you haven’t tried on a pair of loafers recently, give them a shot. They’ll make you feel good, a little bit fancy without looking out of place or overly dressed up. Just make sure to pay attention to the details.