Dark Brown Penny Loafers for Men

These penny loafers give you a dark brown slip on that is smart enough for the office and easy enough for the weekend, with a firm heel counter that stops the shoe slipping as you walk. They are Goodyear welted on a leather sole and made to order in US sizes 5 to 16.5, in standard or custom width.

Why the penny loafer is the one loafer to own first

The penny loafer gets its name from the slotted strap across the vamp, where students in the 1950s tucked a coin. It has stayed popular because it covers more ground than any other slip on. In dark brown calf it works with a navy or gray suit, with chinos and a blazer, and with dark denim, so a single pair fills the gap between dress shoes and casual shoes.

• Smart enough for business casual.
• Easy enough for weekends and travel.
• Dark brown hides scuffs better than tan.

The heel counter, the part that stops loafers slipping

Heel slip is the most common complaint about loafers. With no laces, the shoe is held only by the throat across your instep and the counter around your heel. A soft counter lets the heel lift and rub. Our loafers use a firm heel counter that keeps its shape and grips the back of your foot, so the shoe moves with you instead of flapping as you walk.

• Firm heel counter holds its shape for years.
• Snug throat keeps the foot from sliding forward.
• Cork footbed molds to your foot over the first weeks.

Specifications

How this compares

Classic American penny loafers are often hand sewn moccasins with a glued or stitched rubber sole. A welted penny loafer is built differently.

Fit and sizing

Loafers run larger than lace ups, so expect to take less than your lace up size. Order snug across the instep, because the leather relaxes a little with wear and nothing can be tightened later. Your heel should lift only slightly when you walk. Measure against the men's shoe size guide and send us your measurements if you are between sizes.

• Between sizes: take the smaller length.
• Narrow or wide through our made to order service.

Care

• Brush after each wear.
• Use a dark brown or neutral cream sparingly every few weeks.
• Rest a day between wears and use cedar shoe trees.

What to wear with dark brown penny loafers

• Navy or gray suit in a business casual office.
• Gray flannel pants and a navy blazer.
• Khaki or olive chinos with an oxford shirt.
• Dark denim and a knit for weekends.

Frequently asked questions

Why is it called a penny loafer?

The name comes from the slotted leather strap across the vamp. In the 1950s American students began tucking a coin into that slot, some say for luck and some say so they always had enough to make a phone call. The habit gave the shoe its name and it stuck. Today the strap is mostly decorative, but it is still the detail that makes a penny loafer instantly recognizable and sets it apart from tassel and bit loafers. It is still the most recognizable loafer in American menswear.

Are dark brown penny loafers good for the office?

In a business casual office, they are one of the best shoes you can wear. Dark brown calf looks polished with gray or navy pants and a blazer, and it works with a suit in a relaxed dress code. For a conservative office, black tie or a funeral, a plain black oxford is still the safer choice. Dark brown also hides scuffs and wear better than tan, which makes it practical for daily use. It is a shoe you can wear four days out of five.

How do I stop loafers slipping at the heel?

Start with the right size. Loafers run large, so most men need less than their lace up size, and a shoe that feels comfortable on day one usually slips later. A firm heel counter, like the one in these loafers, grips the back of your foot and keeps its shape. Thin dress socks help grip too. If a pair still slips slightly, a cobbler can fit a small heel grip inside the counter. Most slip happens when a loafer is simply a half size too big.

Can you wear penny loafers with jeans?

Yes, penny loafers and jeans are a classic combination. Choose slim or straight dark denim, hemmed or cuffed so it sits just above the shoe. Dark brown calf gives a smarter look for evenings, while suede feels more relaxed. Add a knit or an oxford shirt and a casual jacket. Avoid very baggy or distressed jeans, which make a sleek loafer look lost under too much fabric. Burgundy or navy socks add a little color without clashing. Burgundy socks add color.

How long do Goodyear welted penny loafers last?

With rotation and basic care, a Goodyear welted loafer can last ten years or more. Because the sole is stitched to a leather welt rather than glued, a cobbler can replace it several times while the upper stays intact. Use cedar shoe trees after every wear, rest the pair a day between wears and condition the leather every few weeks, and the calf upper will outlast several soles. That makes the cost per wear lower than most cheaper pairs. Resoling is simple.

Should I choose calf or suede penny loafers?

Choose calf if you want the more versatile and dressier pair. Smooth dark brown calf takes a polish, handles light rain better and looks right with a suit as well as with jeans. Suede is softer and more relaxed, and it suits spring, summer and weekend wear best. Many men start with dark brown calf as their first loafer and add a brown suede pair later, since together they cover almost every occasion. Both are made to order in the same widths.

See the same style in suede, patina and other colors in our men's leather loafers collection.