Undeniably classic, the preppy thing is a mix of school girl blazers, crisp button-up shirts, comfy loafers, and, perhaps the preppiest of them all, the cardigan. Mix up a few pieces in navy or oxford blue, but throw in some stripes, some pops of orange and some rich gold accessories (or pearls, if you want to go all the way). Our inspiration is Carolyn Bessett Kennedy, a beloved fashion icon known for her East Coast style. Her unique mix of minimalistic and preppy certainly left a legacy.
1. Boy. by Band of Outsiders Cropped Double Breasted Blazer ($1110)
The fitted navy blazer took the fashion world by storm when Kate Middleton wore one out and about this summer. This version offers plenty of preppy detailing: notched collar, lightly padded shoulders, 2-button closure with 4-button detail at front, welt bust pocket and flap hip pockets, double back vents and 4-button cuffs with bracelet sleeves, and striped lining.
2. Markus Lupfer Striped Mohair and Lurex Cardigan ($460)
The cardigan is the cornerstone of preppy style, and the definition of a staple wardrobe item. Preppy with a pencil skirt, a little more daring with a leather mini, this Markus Lupfer pops with its bold orange and blue stripes and metallic buttons.
3. McQ – Alexander McQueen Striped Button Down Shirt ($410)
Menswear-inspired, but a girl’s best friend. A classic blue button down pairs well with slim jeans (a la Bessett) or goes office preppy with a pencil skirt and cardi. This slim, fitted version takes the cake with its oversized fold-over collar, single-button cuffs, and darting at bust and waist.
4. Jeffrey Campbell Mocky Suede Penny Driving Flats ($165)
A hybrid of all things prep: the flat, the penny loafer, and the driving shoe…these Jeffery Campbell flats were made for crisp fall weekends, trips to the market, and after-hours relaxing. Extraordinarily comfortable with rubber studs at heel cap, padded footbed and rubber-studded sole.
5. Marc by Marc Jacobs Preppy Leather Pearl Satchel ($498)
Preppy by name, this Marc Jacobs defines the style with its well-defined shape, simple lines, and compact styling. Pebbled leather handbag with contrasting magnetic-patch pocket at the front and a tonal magnetic patch-pocket at the back. Metallic logo lettering and antiqued gold hardware. Rolled double handles and detachable, adjustable shoulder strap.
6. Michael Kors Men’s Oversized Watch ($250)
Stolen from the boys, this sturdy, efficient piece brings solidarity to a girly, preppy outfit. This Michael Kors is classic to the core and will be your go-to gem for years to come. Water-resistant, gold-plated stainless steel watch with link band and chronograph and date wheel at face.