Oak Street Loafer Review | My Most Worn Summer Shoes 

The idea of wearing loafers might seem far too stodgy for a high schooler, but as you get older and appreciate the craftsmanship and legacy of fine leather footwear, well… you want something nice you can wear with shorts. 

That was my journey from sneakers to boots to loafers: I found that the instant the weather warmed up, all my sartorial know-how went out the window, and I would just spend summer in t-shirts and Chuck Taylors. But loafers satisfy that urge to wear quality even when it’s warm, and Oak Street Bootmakers’ Beefroll Loafer is the model that shepherded me to this point of enlightenment.

I own a lot of different types of loafers now. Horsebit for business casual, tassel for smart casual, chiseled for suits, but the model I find myself slipping on time and time again is Oak Street’s. Why? Three big reasons: it’s unlined (so it breathes well), it’s Blake stitched (so it’s lightweight yet resoleable), and the beefroll element makes them casual enough for t-shirts. 

That casual element might put some guys off, but beefroll loafers are a hidden gem of a casual shoe that, like a moc toe boot, is casual, but it makes a casual outfit look well put together.

Let’s talk a little more about it.

Who Should Buy Oak Street’s Beefroll Loafer

• Guys who appreciate American-made goods.
• People looking for a summer loafer: the leather sole and lack of lining make it breathe well.
• Men who prefer the lightness and flexibility of Blake stitches.
• Anyone curious about the rare shoemaking practice of handsewn moccasins.
• Guys who want a loafer that dresses down easily.

Who Shouldn’t Buy Oak Street’s Beefroll Loafer

• Guys who want the sturdy feel of a Goodyear welt.
• People who want a versatile loafer that can be worn with a suit.
• Folks who prefer the structure of lined loafers.
• Men with wide feet.
• Anyone who wants a wide range of colors to choose from.

Why Oak Street’s Loafers Are Different

As signaled by the name, the Chicago-based Oak Street started out making boots and eventually branched into other casual-but-well-made footwear like derbies, boat shoes, and the loafer. 

Something you might not know is that most moc toes are fake. Whether they’re moc toe boots or moc toe loafers, that horseshoe of stitches on top of the toe is typically decorative. Sometimes, it’s sewn into one piece of leather, sometimes, it’s holding two pieces of leather together, but what it’s mimicking is genuine handsewn moccasin construction. 

What does that mean? Long story short: instead of the leather folding over the top of the foot and getting stitched to the sole, picture standing on the leather and the leather folding up around your foot and getting stitched to the top of the shoe. (That bit is called the plug.) 

It’s a little like making a shoe upside down, and it means there’s one piece of leather that’s both under and to the sides of your foot. This means there are fewer seams to potentially irritate the foot, and it also means the shoe will better mold to the shape of your foot with time. Because of these two elements — or the one element of that one piece of leather where normally there are several seams — many find this to be more comfortable.

Very, very few companies still do genuine handsewn construction, but Oak Street recruited the folks at Maine’s Rancourt & Co to make their loafers the old-fashioned way — and to do it in the United States. I visited that factory, and you can get a nice, close look at the process here.

The Downsides of Genuine Moc Construction

The upsides are the comfort and the fact that you’re helping to perpetuate this vanishing art form in shoemaking. The downsides, if you consider them downsides, are that the more pronounced moc stitching dresses the loafer down a tad, and these kinds of loafers aren’t made with Goodyear welts, which are more durable and can endure more resoles. 

The Best Summer Loafer? 

But these downsides create a much more flexible and lightweight loafer than Goodyear welted options (like Grant Stone’s loafers). And these are unlined with leather soles, so you’ve got the perfect summer shoe: light, breathable, and, dare I say it, a fine option for going sockless. 

There are upsides to leather lining, sure: lining helps a boot or shoe keep its structure and stops it from collapsing on the toes like Oak Street’s probably will with years of wear. But most pros have cons and most cons have pros, and in this case, I’ll take the less structured look over the better breathability, especially because this is a pretty casual loafer. 

The Skinny on Beefrolls

The rolls of leather on the sides of the penny strap are called “beefrolls” because they look a bit like beef roast wrapped up in twine. 

When we sat down with shoemaker Justin FitzPatrick to talk about how to wear loafers with a suit, he agreed. “No suits.” 

But for guys who worry that loafers are too formal — or even too business casual — to wear with shorts and a t-shirt, erring on the side of beefroll loafers is a good way to go.

I’ve worn my Oak Street loafers with everything from linen trousers and button-ups to shorts and a t-shirt, and as long as there are no graphics or patterns on the t-shirt — a good rule of thumb for any guy wearing a t-shirt over 25, to be honest — Oak Street’s loafer is dynamite.

Sizing Oak Street’s Loafers

With their boots, Oak Street stands out for suggesting you order your true size or your Brannock size — that’s the number you get when you measure your foot on a Brannock device in a shoe store.

For their loafers, however, they suggest sizing down one whole size. I’m usually 11.5 and I ordered a 10.5 in these. My toes sometimes hit the end of the toe box, but that’s loafers for you: you want them to be fairly snug. 

Note these loafers run from size 6 to 16, but there are no wide widths. If that’s you, consider Grant Stone’s loafer.

The Price: Are Oak Street’s Loafers Worth It?

Right now, these loafers cost $348.

When you remember that they’re made in the USA — with leather tanned in Chicago, no less — it’s a justifiable price. It’s not a great deal, but when it comes to American-made loafers, your options are typically Alden (Goodyear welted, $680+) or Allen Edmonds (same handsewn construction, $395). Allen Edmonds has a Goodyear welted loafer you can pick instead, but that’s more expensive at $425.

Indeed, while the handsewn element is very cool and very rare, it’s actually cheaper to make loafers like Oak Street’s than to make a Goodyear welted one like Grant Stone. 

In any case, Oak Street’s loafers are fairly priced. The closest competitors — as in, loafers made in the US with this construction — are Quoddy, which is pricier, and Rancourt, which are cheaper but usually takes months to be made for you. 

Personally, I’m thrilled with Oak Street’s Beefroll Loafers. They could use more leathers and more widths, yes, but if you’re looking for a regular loafer for a regular foot, these are my ideal casual summer loafers, and there’s much more to them than meets the eye.