Oxfords, introduced in the 1840s, remain versatile classics. Suited for tuxedos, business attire, and casual wear, they are essential for black-tie events. Featuring a closed lacing system, Oxfords come in styles like cap toes, whole cuts, and brogues. Cap toe Oxfords are a wardrobe staple, while plain patent leather pairs perfectly with a tuxedo. Brogue Oxfords offer additional style options, available as full or semi-brogue.

Loafers are laceless, ankle-exposed shoes with a moccasin-like welt on the vamp and Oxford-style soles and heels. Two notable types are Tassel loafers, which feature dangling tassels and a more formal appearance, and Penny loafers, which originated in 1950s USA. Penny loafers gained popularity among Ivy League students, who would insert a penny into the leather strap for luck, giving the style its name.

Monk shoes are distinguished by their decorative metal buckles, available in single-strap and double-strap varieties. More versatile than Oxfords and Derbies, monk shoes suit both casual and formal wear. A dark brown double monk with full brogue is a stylish choice for men's wardrobes, complementing wool or tweed suits particularly well. This adaptable shoe style offers a timeless, elegant option for various occasions.

Derby shoes, introduced in the mid-19th century, feature an open lacing system where the quarters with lacing overlay the vamp, distinguishing them from Oxfords. This design lends Derby shoes a more informal appeal, making them ideal for pairing with casual outfits. Black Derbies offer a formal look, while brown ones add casual sophistication. The open lacing system provides extra comfort and flexibility, making them suitable for wider feet.

Sneakers rose to popularity among youth in the 1950s, transitioning from sports courts to fashion runways. This shift from subculture to mainstream was tied to Hip Hop culture's growth. Now a staple in everyday wardrobes, sneakers offer ideal footwear for active lifestyles and their versatility extends to the workplace. Available in high, mid, and low-top cuts, as well as lace-up or slip-on styles, sneakers have diversified significantly.

Boots are essential wardrobe items, particularly for colder weather. Featuring a high ankle and often a double leather sole with water-resistant outsoles, they're suitable for urban and rural environments conditions. Main categories include classic lace-up boots, desert boots, and Jodhpur boots with their strap and buckle. Many boots incorporate rubber soles for improved winter traction and to shield the leather sole from moisture.

Chelsea boots are ankle-length footwear with round toes and low heels. Laceless, they feature back quarters sewn to the vamp with loops for easy wear. A flexible stretch covering most of the ankle, often in a contrasting color, is characteristic. Made from box calf leather or suede, Chelsea boots are known for their ease of wear and elegance. They pair well with casual suits, making them popular for informal occasions.

Drivers, or moccasins, are influenced by traditional moccasin design. They feature a double sole for durability and rubber nubs for grip, making them ideal for driving. Unlike their classic counterparts, drivers often have a closed toe and may include a small heel for support. Their unstructured design and soft construction provide optimal comfort and sensitivity while behind the wheel, but they are not suitable for extended walking.