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Black leather shoes by BOSSBlack leather shoes by BOSS
Dress code: shoes worth investing in

Which shoes should any well-dressed gent have in his closet? The following pairs will ensure you’re ideally shod for any occasion.


With its distinctive buckles, this shoe is said to have begun in the abbeys of Europe as a more durable alternative to monks’ sandals. The monk strap features one or two buckles, while other details vary, giving the shoe either a more formal or casual look. As a rule, the more decorative the monk, the less formal it is. Worn with slim-cut pants, the monk strap can become the focal point of an ensemble by teaming it with colored socks or even wearing it barefoot.

Black monk strap shoe by BOSSBlack Oxford by BOSS
The dress slip-on

For any occasion that calls for a tuxedo, this laceless shoe is the one to wear. Choose a black style, ideally in glossy patent leather, which references the lustrous elements of the suit, such as the satin lapels or the stripe down the side of each leg. The dress slip-on is best worn with knee-high socks made of silk or very fine wool. For an elevated look, wear colored or subtly patterned socks, but black is a fail-safe option.

Black dress slip-on by BOSSBlack dress slip-on by BOSS
The Derby

In contrast to the Oxford, the Derby features open lacing: the facing is stitched on top of the vamp, which makes the shoe easier to slip on and provides a more comfortable fit, especially for wider feet. The Derby often forms the basis for other styles, such as Brogues. A Derby is a good alternative to an Oxford for business meetings, but is slightly less formal.

Black Derby by BOSSBlack Derby by BOSS
The Penny Loafer

This shoe got its name from the American Ivy League universities, where legend has it students would slip a penny into the leather strap on the vamp to bring them good luck in their exams. The Penny loafer is the supreme smart-casual shoe, and can be worn with slim-cut jeans or chinos for a refined off-duty look, but can also add a dapper touch to a business-casual blazer and gray pants. For impact, wear them barefoot or with colored socks; pants should be slim and smartly cropped at the ankle.

Dark brown Penny loafer by BOSSGray desert boot by BOSS
The moccasin

One of the most enduring shoe styles in the world, the moccasin is worn by Native Americans, with each tribe having its own decorative details. This design's main characteristic is that it isn't welt stitched. Instead, the leather upper continues into the sole, almost like a sock, and the sole is sewn directly onto it. The result is a soft, casual shoe that clings comfortably to the foot; it is best worn barefoot with either jeans or shorts during the warmer months.

Beige Moccasin by BOSSBlack monk strap by BOSS
The Oxford

The ultimate gentleman’s shoe, the Oxford is defined by its closed lacing: the facing is stitched under the vamp, which gives it a sleek and flattering silhouette. Its timeless design makes it suited to a variety of ensembles, especially business and formalwear. A semi-brogue Oxford features brogue patterning on the toecap, along the facing and on the back of the heel. A traditional black Oxford is the ideal partner for a gray business suit; brown Oxfords are an elegant match for blue suits.

Black Oxford by BOSSBlack Chelsea boot by BOSS
The sandal

Traditionally resonating with the more comfort-focused man, sandals have been transformed into a summer style essential in recent years and should receive as much attention as the other footwear in your closet. Refined calf leather straps are a must, while an EVA rubber sole will ensure the perfect balance of fashion and function. It should go without saying, but we’ll add a reminder just in case: no socks.

Brown casual sandals by BOSSBlack dress slip-on by BOSS