The Well-Heeled Boat Shoe
Get on board with the preppy perennial, now with heels and color.
Splurge: Sail away to the height of glamour with this witty peep-toe stiletto. Stitched and laced just like the classic model, it's got a sporty sort of sex appeal. Christian Louboutin; $1,195; 310-247-9300
Steal: Moccasin-style fringe meets seaworthy lacing on a yellow patent leather shoe—a bright idea with khakis or cropped jeans. Tommy Hilfiger; $59; Macys.com
Good Deal: A mischievous variation on the nautical theme, this mock-croc patent leathr and canvas wedge is from the same company that pioneered the boat shoe in 1935. Fun for weekends, but also appropriate for the office (try it with a gray pantsuit). Sperry Top-Sider; $120; SperryTopSider.com