Photo of Princess Caroline in the late 80s/early 90s via Simplicity City.

I'm always drawn to camp moccasins and driving mocs, probably because of their obvious menswear appeal, but have never felt like I could really pull them off without looking overly conservative or preppy. I stand completely corrected because Princess Caroline shows me how it's done with a long trench, a bandana headband and all black. I'll probably leave the white socks to the professionals though.

Top to bottom: Quoddy Dawson Moc ($300); Minnetonka Classic Driver ($54); Rancourt Camp Moc ($185).