1. Hipster: Mark McNairy’s take on the revitalized double monk strap features full grain leather detailing and vintage-inspired soles made by renowned English manufacturer Dainite. $395 at Indigo & Cotton
2. Splurge: The daring dude willing to pony up for high fashion can find his perfect fit in the “Riviera blue” python moccasin with antiqued silver horse bit hardware and a leather sole.
$980 at Gucci
3. Artsy: Black-wash suede creates a handsome backdrop for contrasting red stitching and crafted metal hardware in Donald J. Pliner’s “Danit” loafer with a full leather lining. $250 at M. Dumas & Sons
4. Basic: Slip into classic luxury with Magnanni’s “Sauron” leather penny loafer in “cognac” with a stacked dark brown leather heel. $350 at Gwynn’s of Mt. Pleasant
5. Exclusive: Handmade in Italy, the “Bubble Toe Oxford”—with a dark brown calfskin upper and black calfskin saddle—offers a formal invitation to pure quality and style. $375 at Billy Reid