Dress with Class: The 10 Commandments of Preppy Style

Consider this your preppy style bible.

I. Thou shalt patronize Brooks Brothers, J.Crew, and Ralph Lauren.

A true prep’s wardrobe wouldn’t be complete without the aforementioned brands. Other brands that suit the preppy lifestyle are Lacoste, Kate Spade, Lilly Pulitzer, Tommy Hilfiger, L.L. Bean, and Tory Burch.

II. Thou shalt monogram every single thing you own.

No one really knows how monogramming came to be associated with preps but if J.Crew makes it, monogram it. You can monogram sweaters, button down shirts, bags, jewelry, notebooks, and even your phone case.

III. Thou shalt not cheat on preppy wardrobe essentials.

Tempted to grab that fast-fashion “cashmere” sweater instead of buying the upscale version? Don’t. Preppy essentials should develop character over time and that’s something a frugal purchase just won’t do.

IV. Thou shalt utilize every single color known to man.

Nantucket Reds, millennial pink, neon green – you name it – it’s probably been worn by the Ivy Leaguer. The general rule when it comes to color? Tone it down with a navy blazer, white button down or beige chinos. There are always plus points for having an extensive collection of colored trousers.

V. Thou shalt know the importance and versatility of loafers.

The few times you won’t be in loafers will be when you’re doing sports. So it’s best to stock up on these laceless favorites as you’ll be living in them. You can choose from penny loafers and horse-bit loafers to tassel loafers and smoking loafers.


VI. Thou shalt not covet your neighbor’s collection of ribbon, brown, braided and printed belts.

A post shared by Kiel James Patrick (@kjp) on

Aside from loafers, you should value the power of belts. Typically in ribbon, brown, braided and printed variations—one for every preppy-related occasion and mood.

VII. Thou shalt value the power of nautical dressing.

The Navy blazer, Breton stripes, and anchor bracelet are all important components of the coastal look. Adapted from the French, the beauty of nautical dressing lies in its ability to look both casual and chic.

VIII. Thou shalt not take off thy pearl necklace.

While many types of jewelry are accepted, pearls are an easy way to be delicately preppy. Heritage is a detail valued by many preps, so you don’t need to look further than your own family’s heirlooms.

IX. Thou shalt tie your cable-knit sweater around your shoulders.

Sweaters are, without a doubt, a preppy essential. In warmer climates, your style doesn’t have to be compromised. Simply wrap that sweater around your shoulders and loosely tie sleeves together. Infamous as the styling hack may be, it’s still incredibly useful.

X. Thou shalt embrace prints.

Jackie Kennedy in vintage Lilly Pulitzer

Tastefully injecting print into your preppy wardrobe is an art form. There’s plaids, florals, embroidery, madras, animal, paisley, gingham, and all things Lilly.

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Paolo Chua
Paolo Chua is the Associate Style Editor of Esquire Philippines.
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