The booties from Ermenegildo Zegna stand out for the sophisticated rhino-effect leather characterized by a naturally wrinkly texture that plays up the shoes’ “greige” hue. The round-toed upper is defined by a few slits; the shoe is kept in place courtesy of an elastic ankle band, elegantly covered in leather. The sole is crafted from brown leather and rubber.

These ankle boots proposed by Dries Van Noten for Winter 2020 have a clear 70s vibe, a rounded toe and a fairly high heel. The warm hue of the leather further highlights the shoes’ vintage inspiration. The boots’ basic style features a concealed zip, while the thick sole is crafted from natural leather.

The ankle boots from Rochas are quite similar. Crafted from a luxurious burgundy velvet, and with a slightly pointier toe, this is the perfect style for the upcoming holidays if you are a vintage lover.

Buckles, straps and embellishments characterize the trendiest men’s ankle boots for Winter 2020. This design from Amiri stands out for its cowboy boot inspiration featuring a pointy toe and angled heel. The black leather upper is embellished by a double crisscross ankle strap with flashy gold-toned buckles and a further strap adorned with a golden enameled chain.

The ankle boots spotted on Dior’s Fall Winter 2020 men’s runway stand out for their classic design revamped by ultra-modern details. The black brushed leather upper features a contrasting thin strap tied around the ankle that fastens through a special metal buckle with three different finishes and the house’s logo. The round toe takes on an edgier vibe courtesy of a gleaming metallic profile, while the sole is crafted from black leather.

These chelsea boots from Valentino Garavani are a masterclass in contrasting elements. The shoe’s chunky structure and black rubber rugged sole are toned down by a subtle hued floral motif across the sturdy toe. The instep is kept in place with an elastic strap featuring the house’s VLogo.