Preppy Vests first appeared on Chictopia's streetstyle gallery in Winter 2009 seen on Washington blogger districtofchic of districtofchic.com. She styled her black Forever 21 sweater vest vest with a blue J Press oxford shirt, black American Apparel lame leggings leggings, and black Pour La Victoire open toe boots. Since then, Preppy Vests have grown in popularity as bloggers from Manila, Jakarta, and San Francisco have discovered them. Popular brands of Preppy Vests are thrifted, Zara, Forever 21, H&M, and vintage.
There are currently 390 streetstyle photos of bloggers wearing Preppy Vests. Most recently, blogger redhaireddesigner of vintageredheads.blogspot.com wore her navy H&M denim vest with a dark brown Ardene oxfords shoes, mustard H&M wool tights, and carrot orange H&M top.