Sole Mates: Why the Double-Buckle Shoe is an All-Season Favorite

Spotlighting menswear-inspired, monkstrap shoes in this next iteration of our footwear series, which explores how to wear must-have silhouettes.

Olivia Palermo Collection blazer and blouse; Agona trousers; Piaget necklace; Hermès scarf; Santoni shoes.

Now that we're in month two of donning comfortable attire and loungewear, it's only natural to imagine what we'll wear when it's finally time to emerge from the home. Will we be inspired to shed the athleisure for good and opt towards more structured staples that are perhaps on the sidelines for now? When thinking about fresh ways to dress, one thing is for sure: high-quality items that are built to last are the pieces that'll matter.

In the footwear realm, one of the most enduring styles of all time is the double monkstrap shoe. The name derives from the source inspiration as modern dress shoes were originally modeled after the buckled sandals that monks wore throughout the Middle Ages. Today, whether the buckle details are adorned on a brogue shape or a loafer, the shoe's sleek silhouette is always versatile and pairs just as well with suiting as it does with jeans or dresses. The lace-less design also means the shoe is easy to slip on or off from fall through summer, and styles crafted from heritage houses that merge tradition with innovative design have an extra-special touch.

Giuseppe Santoni, CEO of the Italian shoemaking brand Santoni, explains why the double-buckle style is a signature for the family-run brand. "This style has a strong identity and an unmistakable design, which can be easily worn in every occasion or even with a more informal outfit," he says, "Our collections are inspired by masculine codes but reinterpreted in a feminine and chic way. We love to borrow iconic elements from the traditional menswear universe, like the the double-buckle, and add an unconventional combination of colors and materials to harmonious proportions. The result is sleek yet sophisticated creations."

How do you style the monkstrap, a style so distinctively full of character?  Have them anchor flirty, summery skirt like how Olivia styled her namesake label, or try them with flared trousers and a blazer for an updated Pitti Uomo-like moment as the weather cools. Olivia also loves wearing double-buckle flats with her favorite wardrobe staple: slim leather trousers. Perennial monkstrap shoes are worth hanging onto for seasons and seasons, and artisanally crafted styles may even patina, meaning the leather styles gets even better with age.

Credits Photographed by Olivia Graham; Styling/Creative Direction by Jacqueline Zenere; Makeup by Robin Schoen; Hair by Elsa Canedo; Modeled by Bruna Tenório. Special thanks to The Pierre, A Taj Hotel, New York
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