When “Preppy outfit” is mentioned, most people envision a navy blazer, a crisp Oxford shirt, chinos, loafers, and a preppy tie – the quintessential Ivy League style.

However, the realm of Preppy fashion is much more versatile and imaginative than one might think.

Preppy styles evolved, blending cherished classic elements with trendy aesthetics from different eras and subcultures.

In this article, we’ll introduce you to 11 captivating Preppy outfit ideas that are anything but conventional.

From the glamour of the 80s and 90s to the mystique of Preppy Goth, the comfy vibe of Preppy Boho, and the cute flair of the Preppy Cowgirl, there’s an ensemble here for every sartorial adventurer.

1. 80s Preppy Style Outfit Idea

Start your 80s Preppy style outfit with a white silk notch collar button-up blouse to reflect the decade’s sophistication.

Layer the blouse over a patchwork sweater vest, capturing the era’s affinity for including British aesthetic elements into the classic Ivy League Preppy look.

Include a high waist A-line plaid midi skirt to accentuate the throwback vibe while retaining the Preppy aesthetic.

Complete the retro Preppy look with knee-high faux leather boots in a crocodile pattern that’ll bring out the 80s audacious side.

2. 90s Preppy Style Outfit Idea

For the 90s Preppy style outfit idea, begin with a white V-neck blouse with long sleeves to set a classic and clean base.

Top it off with a plaid print crop blazer in brown, reminiscent of the decade’s plaid craze, and a pleated skirt in a similar shade, a signature piece in the 90s Preppy wardrobe.

Slip into over-the-knee socks for that quintessential schoolgirl charm and opt for black leather lace-up shoes with chunky soles to ground the look with a touch of 90s grunge.