Men's Olive Green Penny Loafers

Men's olive green penny loafers, Goodyear welted on a leather sole and made to order in your size and width. Olive is the green that works where others do not, and a penny loafer is the shape where an unusual color asks least of you.

Why olive behaves where other greens do not

Green is the color most men never consider, and the reason is that most greens are cool. A green mixed toward blue fights every warm thing in a normal wardrobe: brown tailoring, tan chinos, any brown leather, and the shoe ends up looking like it was bought for a different outfit.

Olive is green pulled toward yellow and brown. It sits in the same temperature family as the clothes most people already own, which is why it reads almost as a neutral. From ten feet it looks closer to a warm dark brown than to a color. Up close the green shows.

The test: if you can name the green from ten feet away, it is too bright for a dress shoe. Olive passes that where grass or emerald does not.

Olive also polishes unusually. Brown lightens and warms at the toe with wax, drifting toward tan over the years. Olive deepens instead, because wax darkens the yellow in it, so an olive shoe at three years is a richer shoe than it was new.

Why a loafer is the easiest shape for an unusual color

This is the argument for buying olive on a slip on rather than a lace up.

A lace up is a formal shape. Put an unexpected color on an oxford and you create tension: a serious silhouette in a color nobody anticipated. That is a strong effect and not everyone wants to make it.

A loafer is already relaxed. No lacing, no hardware, a shape that has never pretended to be formal. An unusual color on it reads as considered rather than as a statement, which is why a colored loafer is the easiest way into colored footwear and a colored oxford is the hardest.

The vamp also helps. A penny loafer has the largest continuous panel of any dress shoe, running unbroken from the toe to the throat, so a color has room to show its depth rather than being chopped into pieces by seams and eyelets.

Dyed through, or sprayed on top

This decides how the shoe looks in three years, and it is the single most useful thing to check on any colored shoe.

The check: look at the flex crease across the vamp of any worn colored shoe. On dyed leather the crease is the same color, slightly deeper. On a sprayed finish the crease is a visibly different line, because the film has thinned and the hide is showing through.

There is a shortcut worth knowing. A shoe that can take a hand layered patina cannot be corrected grain, because dye will not penetrate a coating and the process would fail. If you want to know what leather is under a finish, look at what the finish is capable of.

What makes a penny loafer well made

A saddle strap runs across the vamp with a slot cut through the middle. 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 good one from a cheap one, and all three are visible in a photograph:

• The saddle should be a separate piece of leather stitched down at both ends, not glued on or stamped into the vamp. Those two stitch points take every bit of tension the strap ever sees, and a glued saddle lifts at one end within a couple of years and never sits flat again.
• 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.

"Loafers always slip at my heel"

This is the most common complaint about loafers and it is almost always a length problem rather than a loafer problem.

A loafer has no lacing. Only the throat line and the heel counter hold your foot, so if the shoe is even slightly too long your foot slides forward as you step and the heel lifts out. No amount of breaking in fixes it, because nothing about the shoe changes its length.

• Loafers run large relative to lace ups on the same last, so most people take less than their lace up size here.
• If it is comfortable the first time you put it on, it is too big. A correctly fitted loafer feels firm on day one and eases as the cork bed compresses to your foot.
• Do not size up for width. Order your true length and specify the width separately, because sizing up makes the shoe long and a long loafer slips permanently.

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.

Stitched saddle with beef rolls and finished slot edges, firm heel counter, leather lining, leather sole, stacked leather heel. 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: 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.

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.

What to wear them with

• Strongest: stone, tan and cream chinos. Olive and a warm neutral is the cleanest pairing there is.
• Works: brown and tan tailoring, tweed and moleskin, mid and charcoal gray, dark denim.
• Avoid: navy, which is cool and sits too close in depth so both go muddy, and black, which flattens the olive entirely.
• Do not match: no olive tie, no olive belt. One olive item is deliberate, two is a theme.

Match your belt to dark brown rather than chasing the green. Also in the range: the olive green patina derby and the black penny loafers.

Care

Cream first, then wax on the toe and heel counter, the two areas that do not flex. Use a neutral or olive cream rather than a brown one, because brown cream on olive pulls it toward a flat khaki over a year and the shift does not reverse.

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. Brush along that seam rather than across it.

Keep the shoes out of direct sunlight, which lifts a mid tone color faster than a dark one. Cedar trees between wearings, a day of rest between wears, dry naturally away from heat.

What to expect when you order

Cut and lasted after you order in your size and width. Leather takes dye differently hide to hide and a mid tone shows that variation more than a dark color would, so your pair will be close to the photographs rather than identical. Production is 10 to 14 days, then shipping.

Questions we get asked

Is olive green wearable on a men's shoe?
Yes, more than other greens, and the reason is temperature. Most greens are cool and fight every warm thing in a wardrobe. Olive is green pulled toward yellow and brown, so it sits in the same family as clothes most people already own and reads almost as a neutral.

How dark does the green need to be?
Deep enough that you cannot name it from ten feet away. Olive passes that test where grass or emerald does not.

Why is a loafer easier for an unusual color than an oxford?
Because a lace up is a formal shape, so an unexpected color on it creates tension not everyone wants to make. A loafer has never pretended to be formal, so an unusual color reads as considered rather than as a statement.

What is the difference between dyed through and sprayed color?
Dyed through means the dye penetrates into the fiber of the hide, so a scuff removes finish and the color underneath is the same color. A sprayed pigment film sits on the surface, so a scuff exposes the hide beneath and the flex line cracks as a visible seam.

How can I check whether a colored shoe is dyed or sprayed?
Look at the flex crease across the vamp of a worn pair. On dyed leather the crease is the same color, slightly deeper. On a sprayed finish it is a visibly different line, because the film has thinned and the hide shows through.

Does olive polish like brown?
No. Brown lightens and warms at the toe with wax, drifting toward tan. Olive deepens instead, because wax darkens the yellow in it, so an olive shoe at three years is richer than it was new.

What makes a penny loafer well made?
Three things visible in a photograph. The saddle should be a separate piece stitched down at both ends rather than 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.

Why do my loafers slip at the heel?
Almost always because they are too long. With no lacing, only the throat line and the heel counter hold your foot, so a shoe even slightly too long lets your foot slide forward and the heel lift. Breaking in does not change length.

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 permanently.

What cream should I use on olive?
Neutral or olive, never brown. Brown cream on olive pulls it toward a flat khaki over a year and the shift does not reverse.