Brand new/never worn - just tried on Size 39 (U.S. 8.5/9) - Fits more like a 8.5 IMO A chunky, flared loafer in immaculate, polished black calf. The broad, square-toe silhouette is accentuated with a triple-layer front welt. Wear it with an ankle sock for a preppy come retro vibe. Polished smooth cow leather upper and leather lining True leather outsole 2” Block heel Slip on style Fits true to size. See size guide. Handmade in Tuscany.