Forget your pre-conceived notions of the Sperry topsider-wearing, Lily Pulitzer-loving, pastel headband-sporting, haughty prepster! Well, for the most part…At the moment, I’m feeling like polishing it up with a wink to New England-socialite style. Emphasis on wink. The best new preppy shoes come with a hearty dose of irony, so it won’t look like you just finished reading The Official Preppy Handbook, circa 1980:

1. Rochas Leather-Trimmed Raffia Loafers: Perform a pattern mash-up by pairing these crisp plaid loafers with stripes or florals for a fully directional look.
On Net-a-Porter for $795.

2. Yves Saint Laurent Maryna Flower-Print Wedges: The preppy lady loves to dress up with a vivid flower print. Oversized blossoms are cheeky, and make a strong counterpart to a blonde wood wedge.
On Ssense for $795.

3. Christian Louboutin Rollergirl Tartan Canvas Loafers: Preppy tartan canvas goes a little badass with chain-trimmed metal toecap, just enough to make them wonder about your true persona.
On Net-a-Porter $995.

4. Manolo Blahnik Pamufac Pump: Nautical stripes plus delicate grosgrain equals a refined pump with a shape that gives a nod to the prep’s original era: the eighties.
At Barneys New York for $655.

5. Balenciaga Arena Buckle Ballerina Flat: Pastel-pink and brogue-esque detailing is classic prepster. But in true Balenciaga fashion, these crackle-leather flats are more than meets the eye.
At Barneys New York for $575.