Men's Black Penny Loafers

Men's black penny loafers in full grain calf, Goodyear welted on a leather sole and made to order in your size and width. If you own one loafer, this is the one, and the rest of this page is about why a welted pair costs what it does and when it is not worth it.

"Why pay this when a loafer costs a fraction elsewhere?"

Fair question, and the answer is not craftsmanship in the abstract. It is that a cheap loafer and a welted one are different objects with different lifespans, and which one is right depends on how often you will actually wear it.

The honest framing is cost per wear rather than price. A welted pair worn twice a week for fifteen years, resoled three times, works out cheaper per wear than replacing a glued pair every two years. A welted pair worn six times a year does not, and you would be better off spending less.

So the question to ask yourself is not whether these are worth it, it is how often you will wear black loafers.

What makes a penny loafer a penny loafer

A saddle strap runs across the vamp with a slot cut through the middle of it. The slot is the defining feature and the name comes from American students in the 1930s and 40s putting a coin in it.

Three details separate a well made one from the rest, and all three are visible in a photograph:

• The saddle should be a separate piece of leather stitched down at both ends, not a strip glued on or a shape stamped into the vamp. Those two stitched points take every bit of tension the strap ever sees.
• The beef rolls, the raised stitched swellings where the saddle meets the sides of the shoe, should be genuine rolls of leather rather than a decorative seam printed into the surface.
• The slot edges should be finished and turned, not raw cut. A raw edge is where the leather starts to stretch, and a stretched slot goes from a neat rectangle to a slack opening within a couple of years.

Why black, and where a black penny actually goes

Black is the most formal color in footwear, which makes a black penny loafer the dressiest version of a fundamentally casual shape. That tension is the whole point of the shoe.

• Works: charcoal and mid gray worsted or flannel, navy, black tailoring. It is the one loafer that will carry a suit in most offices.
• Works casually: dark denim, gray or stone chinos.
• Avoid: brown or tan tailoring, which fights black at every depth. Also avoid anything where the dress code expects lace ups specifically, because a loafer is still a loafer.

If you want one loafer that reaches furthest up the formality scale, black is the color. If you want one loafer that gets worn most often across a normal week, dark brown is usually the better buy, and we would rather tell you that than not.

The four things that go wrong with a penny loafer

• Heel slip. There is no lacing, so only the throat line and the heel counter hold your foot. A loafer even slightly too long slips at every step and no amount of breaking in fixes it. This is a fit error, not a settling issue.
• The saddle ends lift. On a shoe where the saddle is glued or lightly tacked rather than stitched through, one end works loose within a couple of years and the strap stands away from the vamp.
• The slot stretches. With no reinforcement behind it and a raw cut edge, the cut out elongates into a slack opening. Cosmetic rather than structural, but it is the detail people look at.
• Cream builds at the saddle seam. Polish collects in the channel where the strap meets the vamp, dries pale and outlines the saddle in a lighter tone against the black.

Full grain, top grain, genuine leather

• Full grain keeps the complete outer surface of the hide with nothing sanded off. The fibers there are the tightest in the hide, which is why it patinas rather than wearing through and why it takes a shine on the toe.
• Top grain has been sanded to remove scars then coated or embossed. It looks flawless on a shelf and cracks at the flex line within a couple of years.
• Genuine leather is the lowest grade sold despite the name.

On a black loafer this decides whether you can build a shine at all. A mirror finish is thin layers of wax sitting on a tight intact grain. On coated leather the finish is already the surface and wax never bonds to it, which is why cheap black shoes look plastic rather than polished.

How these are built

Goodyear welted and hand stitched. A leather welt runs around the upper and insole and the outsole is stitched to that welt rather than glued to the upper, so the shoe resoles repeatedly without disturbing the upper. Cork fills the cavity between insole and outsole and compresses to your foot over the first month, so the footbed ends shaped to you rather than to a last.

Full grain calf upper, stitched saddle with beef rolls and finished slot edges, leather lining, leather sole, stacked leather heel with a rubber top piece. Width cut to your measurement in D, E, EE or EEE through our made to order service. See the rest of the range in men's leather loafers.

Fit and sizing

Made to order in US sizes 5 to 16.5 with widths D through EEE.

A loafer has to be snugger than a laced shoe. A lace up gives you a second chance, because if the width is slightly off you can adjust the lacing and the leather eventually gives. A loafer gives you nothing: too narrow and it grips across the ball with no way to ease it, too long and it slips at the heel forever.

Loafers also run large relative to lace ups on the same last, so most people take less than their lace up size here. If a loafer feels comfortable the moment you put it on, it is too big.

Order your true length and specify the width separately rather than sizing up to gain room across the ball. Measure against the men's shoe size guide and tell us before you order if you are between widths, have a low instep or get heel slip in loafers generally.

Care

Cream first, then wax. Cream feeds the leather and holds the color every four to six wears; wax builds shine and protects the toe.

Keep product out of the saddle seam. It collects in the channel where the strap meets the vamp, dries pale and outlines the saddle in a lighter tone, which against black is conspicuous. Brush along that seam rather than across it.

Keep wax to the toe and the heel counter, the two areas that do not flex. Wax over the flex area cracks as the shoe bends. Cedar trees between wearings, a day of rest between wears, and dry naturally away from heat if they get wet.

What to expect when you order

Cut and lasted after you order in your size and width. Production is 10 to 14 days, then shipping.

Questions we get asked

Why does a welted loafer cost so much more than a cheap one?
Because they are different objects. A cemented loafer is glued and cannot be resoled, so it lasts one to three years. A Goodyear welted pair is stitched to a welt and resoles repeatedly, so it lasts decades. The honest measure is cost per wear, not price.

Is a welted loafer worth it for me?
It depends how often you will wear it. Worn twice a week for fifteen years and resoled three times, a welted pair costs less per wear than replacing a glued pair every two years. Worn six times a year, it does not, and you would be better off spending less.

What is the difference between Goodyear welted and Blake stitched?
Goodyear stitches the outsole to a welt which is itself stitched to the upper, so no stitch pierces the insole and any good cobbler can resole it repeatedly. Blake runs the sole stitch straight through the insole and upper, which resoles once or twice and only by a specialist.

What makes a penny loafer well made?
Three things you can see in a photograph. The saddle should be a separate piece stitched down at both ends, not glued or stamped. The beef rolls should be genuine rolls of leather rather than a printed seam. And the slot edges should be finished and turned, because a raw edge is where the leather starts to stretch.

Should I buy black or brown penny loafers first?
Black reaches furthest up the formality scale and is the one loafer that will carry a suit in most offices. Dark brown gets worn more often across a normal week. If you only want one and wear tailoring rarely, brown is usually the better buy.

Why does my loafer slip at the heel?
Because it is too long. There is no lacing, so only the throat line and the heel counter hold your foot, and a loafer even slightly too long slips at every step. It is a fit error rather than something breaking in will fix.

Do loafers run large?
Yes, relative to lace ups on the same last, so most people take less than their lace up size. If a loafer feels comfortable the moment you put it on, it is too big.

Should I size up for a wide foot?
No. Order your true length and specify the width separately, D through EEE. Sizing up to gain room across the ball makes the shoe long, and a long loafer slips at the heel permanently.

Why do cheap black shoes look plastic?
Because a mirror shine is thin layers of wax sitting on a tight intact grain. Corrected or coated leather already has a finish as its surface and the wax never bonds to it, so it stays flat however much you polish.

How do I stop polish outlining the saddle?
Keep cream and wax out of the channel where the strap meets the vamp, and brush along that seam rather than across it. Product left in the channel dries pale and outlines the saddle in a lighter tone, which against black is conspicuous.

Can these be resoled?
Yes, repeatedly, by any good cobbler. Goodyear welted construction stitches the outsole to a welt rather than gluing it to the upper, so the sole is replaced without disturbing the upper.