The way to wear a loafer now is with the sock on show: a flash of red, a sheer black ankle, a white rib against tailoring. One black penny loafer, the Elsa ($265, handmade in Milan), and five socks give you five different moods. Here is how to do each one.
For years the rule in our Milan boutique was that a loafer is worn bare or with a sock nobody sees. This season the sock is the point. The loafer steps out with its sock in plain view, and because the Elsa is a slim, unlined penny loafer on a genuine leather sole, it is the polished base for every version below.
One black loafer. Five socks, five moods.
THE LOAFER IN EVERY LOOK
Elsa Penny Loafer
$265 · Genuine leather black · 2 cm heel · US6–US11
True penny loafer with a leather strap and no hardware. Genuine leather upper and leather sole. Handmade in Milan. Also in suede navy, suede tan, leather ivory, leather tan and leather navy.
Cuffed indigo jeans, a cherry-red ribbed sock, and the black Elsa underneath. This is the look I wear to the warehouse on Saturdays. The loafer stays classic so the colour can speak; the cuff has to sit high enough to show at least three fingers of sock, otherwise the red reads as an accident instead of a decision.
02 — Burgundy & Sheer
A glossy chocolate leather midi, a sheer black ankle sock and a tonal burgundy room. This is evening polish without the heel. The sheer sock is what makes it work: it softens the line between leg and loafer and makes the black leather look dressier than it is. Keep the sock short, just above the ankle bone.
03 — Cobalt Tailoring
Camel wool trousers with a deep turn-up, a crisp white rib, and the loafer in black. The menswear classic, lit in colour. The trouser should break just above the sock so there is a clean band of white between hem and shoe. This is the version Giada wears in the Milan boutique most days of the week.
04 — The Knee-High
Grey ribbed knee-highs and a tweed mini. A collegiate reference, made grown-up. The trick is proportion: the sock should end two fingers below the knee and the skirt should end two fingers above it, so there is a narrow band of skin and nothing else. A heavy rib in mid-grey keeps it from tipping into costume.
05 — Golden Hour
Cream wide-leg wool and chocolate socks: warm on warm, with the black loafer as the anchor. The widest trouser in the collection needs the slimmest shoe under it, and the Elsa is exactly that. Let the hem puddle slightly over the sock; this is the one look where a little mess is the point.
The loafer stays classic, so the sock can speak.
Why the Elsa Works as the Base
A loafer only takes a bold sock if the shoe itself is quiet. The Elsa is the penny loafer in the strict sense: a leather strap with the classic cut-out across the vamp, no hardware, a 2 cm stacked heel. It is handmade in our Milan atelier, where my father opened his first workshop in 1986, from Tuscan calf leather on a genuine leather sole that a cobbler can resole. A finished pair has been touched by hand at least seven times. That restraint is what lets a cherry-red sock or a sheer black ankle do the talking.
Show the sock on purpose. Cuff the trouser or shorten the hem so at least two to three fingers of sock are visible between hem and shoe. A ribbed sock in a strong colour (red, white, chocolate) reads as a styling choice; a thin dress sock that barely shows reads as a mistake.
What socks go with black penny loafers?
Almost anything, which is why the black Elsa is the base for every look in this post: cherry-red rib with denim, sheer black for evening, crisp white rib with camel tailoring, grey ribbed knee-highs with a mini, or chocolate with cream wool.
Can you wear loafers with a skirt?
Yes. A penny loafer with a tweed mini and ribbed knee-highs, or with a leather midi and sheer socks, are two of the most current combinations for fall 2026. Keep the sock deliberate and the loafer slim.
Are penny loafers in style for fall 2026?
Yes. The slim, unlined Italian penny loafer is the shoe of the season, worn with the sock on show. It replaces the ballet flat for day and the low heel for evening.
Is the Elsa Penny Loafer comfortable?
Yes. It is a genuine leather upper on a genuine leather sole with a 2 cm heel, handmade in Milan. The leather molds to the foot within a few wears. It runs US 6 to 11; if you are between sizes, size up half.
How should I care for black leather loafers?
Wipe with a soft dry cloth after wear, condition with a neutral leather cream once a month, and store with shoe trees. The leather sole can be resoled by any cobbler.
Con amore,Mike LoprioreDesigner & second-generation Lopriore
