Men's Loafers: Penny, Tassel, Horsebit and Boat Shoes

Men's shoes · Loafers

The loafer is the shoe you slip on. It sounds like a detail, but it is everything: without laces there is nothing to tighten, so the fit must be right the first time and the shape should be chosen with where you will wear it in mind. Under the word «loafer» are four different shoes, and most people who ask us for one do not yet know which of the four they want.

The four styles

The penny loafer has a smooth strap with the horizontal slit at the center - the one where American students used to tuck a coin, hence the name. It is the most understated and versatile shape: it works with a suit and with jeans without changing register. The Sebago Dan is the model that defined the category, and remains our benchmark.

The tassel loafer - tassel loafer - features two leather tassels on the vamp. It originated as an American lawyer's shoe and has a more distinctive character: it calls for trousers that give it room, so it shows. It is the shape we recommend to anyone who finds the classic loafer anonymous.

The bit loafer has a metal bar across the vamp, sometimes with a double buckle. It is the most formal of the three and also the most recognizable: choosing it means accepting that the shoe will stand out.

The boat shoe is something else entirely: hand-stitched, with a leather lace that runs around the upper and a white non-slip sole, it was created for a boat deck where slipping was not an option. It is the most casual and the only one of the four that is truly worn without socks.

Leather or suede

Smooth leather, polished or brushed, is the formal choice: it holds its shape, can be polished, and develops a patina with age. It is the one to wear with a suit. Grained leather - full-grain leather with a raised grain - conceals scratches and is the most practical for everyday wear.

Suede changes the shoe more than you might think: it softens everything, lowers the formality by half a tone and makes even a formal shape like the bit loafer easy to wear with denim. Protect it with spray before its first outing, not after the first rain. In autumn, it is the material we see people choose most often.

Then there is perforated leather, genuine leather pierced in a pattern: it lets air through and remains the best answer to the question, “a closed loafer in July.” It is not a makeshift summer shoe, but a construction designed for warm weather.

With or without socks

The most frequent question at the counter, and the answer depends on the shape. With boat shoes, bare feet are correct and historically appropriate. With penny loafers and tassel loafers, it works in summer, provided you wear no-show socks — bare feet inside closed leather damage it, and within two seasons the shoe can no longer be restored.

With a suit, you should always wear socks, preferably long ones: a bare ankle under tailored trousers is a bold choice that only works if everything else has been carefully considered. In winter, visible socks, either matching or ribbed, are the most contemporary choice.

With a suit

A loafer works with a suit under two conditions. The first is trouser length: it should just brush the shoe, not rest on it — trousers bunching over the vamp take away the loafer's only clean line. The second is colour, and here the rule is simple: brown with navy is the most elegant combination there is, black with navy is more severe, and black with grey is for formal occasions.

The brands we stock

Sebago is the original American penny loafer, with hand stitching and a construction that softens around the foot: our selection includes the Dan model in black and brown leather, and the Askookfield in suede. Barrett brings Italian craftsmanship to dark brown suede and navy blue, with tassels. Doucal's offers textured leather and the double buckles of Montegranaro.

Fabi is our go-to for suede, Timberland makes authentic boat shoes with leather from LWG-certified tanneries, and Dr. Martens offers the Adrian mounted on an AirWair sole - an unusual yet successful loafer with a dedicated page because it is the one customers ask us for most.

If you are looking for the same style for women, you will find women's loafers; for other styles, lace-up shoes and sneakers. All men's shoes are in men's shoes.

Frequently asked questions

What is the difference between a loafer and a moccasin?

In Italian, the terms are used as synonyms, but they are not quite the same. “Mocassino” refers to the construction: a one-piece upper that wraps around the foot, stitched to an upper vamp, a technique of Native American origin. “Loafer” refers to a slip-on shoe without laces. Almost all loafers are constructed like moccasins, but boat shoes are moccasins with laces, and some modern loafers do not have moccasin construction.

Should you wear loafers with or without socks?

With boat shoes, bare feet are fine. With penny loafers and tassel loafers, in summer an invisible sock works well: bare feet inside closed leather will ruin it within a few seasons. With a suit, socks are always required, preferably long ones.

What size should you get in loafers?

Your usual size, without sizing down. Since loafers have no laces, they cannot be adjusted, so going down a size does not make them tighter: it simply compresses your toes. Leather gives by a few millimetres in width during the first two weeks, suede a little more, but the length never changes. If in doubt, measure your foot in centimetres and compare it with our size chart.

Which loafers can be worn with a suit?

The penny loafer and the horsebit loafer, in smooth leather. The tassel loafer works with a suit but is a more distinctive choice. The boat shoe does not: the white sole and casual construction clash with tailoring. For colour, brown with a blue suit is the most elegant combination.

Can suede loafers be worn in winter?

Yes, and it is actually the season when we see them chosen most often. Suede should be protected with a water-repellent spray before wearing it for the first time, not after the first rain, and brushed with a rubber brush when it starts to look dull. In heavy rain, smooth leather is the better choice.

Are there men's loafers for summer?

Yes, and it is the perforated loafer: genuine leather perforated in a pattern to let air through. It is not a budget version, but a construction designed for warm weather, solving the problem for those who want a closed shoe in July. The boat shoe, also created for the deck, is designed for the warm season too.

For the classic loafer, the reference is Barrett shoes: penny loafers and tassel styles, with a stitched leather sole and non-slip insert.

By type, we have two dedicated pages: tassel loafers and penny loafers.