The term ‘preppy’ is an abbreviation of preparatory, and used to describe the fashions of a student in secondary school.

The style, characterized by a clean, classic, and somewhat conservative aesthetic, became popular in the United States in the mid-20th century.

For most, the look conjures up visions of well-to-do professionals, college-preparatory students or their favorite teen movie villain (think Vivian Kensington from Legally Blonde or Stan Gable from Revenge of The Nerds).

Preppy style remains timeless but forget what you know about it, today’s ‘it’ girls are giving it a 𝓈ℯ𝓍y spin.

The term ‘preppy’ is an abbreviation of preparatory, and used to describe the personal style aesthetic of a student in secondary school

Preppy style remains timeless but today’s ‘it’ girls are livening it up with their own 𝓈ℯ𝓍y spin

Varsity jacket

Varsity jackets are a staple of prep style.

High school girls have proudly worn their boyfriend’s personalized letterman jacket over their uniforms and everyday outfits for decades.

This season the fashion set is giving the sporty outer-layer a feminine spin.

During Milan Fashion Week, a model was spotted outside the Philosophy by Lorenzo Serafini show wearing a leather varsity jacket over nothing more than a black bra and jeans, accessorized with silver sunglasses.

Italian actress Coco Rebecca Edogamhe also opted to go shirtless under her bomber.

While attending the Max Mara fashion show the brunette beauty donned a two-tone jacket over a black bra top and matching skirt.

Jenna Dewan wore a see-through shirt under her jacket at the Phillip Lim show during New York Fashion Week.

Bae Doona teamed her Louis Vuitton varsity jacket with a white slip dress and black boots

Helena Bordon wore a green checkered oversized cardigan as a dress

Reminiscent of grade school uniforms, the knit sweater vest has always been a prep’s hottest layering piece

Sweater vest

Reminiscent of grade school uniforms, the knit sweater vest has always been a prep’s hottest layering piece.

The most traditional way to wear one is over a solid color button down shirt.

To give the basic garment a modern day, cool girl twist, fashionistas like Amalie Gassmann are teaming them with trendy separates.

The filmmaker was spotted on the streets of Paris wearing a sleeveless knit with slouchy boyfriend denim in the same shade.

She accessorized with a trendy Dior handbag and belt.

Outside the Missoni show, a guest styled her grade school throwback over a shirt in a contrasting print and nude underwear.

Polo shirts originated in sports like tennis and polo in the 19th and early 20th centuries

Today’s streetstyle stars are putting their own feminine twist on polo shirts

Polo shirt

Polo shirts originated in the sports world with tennis and polo in the 19th and early 20th centuries.

They offer a polished yet casual look featuring a collar and a buttoned placket.

Traditionally they extend beyond the hips and are tucked into a pair of jeans or khaki pants.

Todays streetstyle stars, however, are teaming their sporty garments with unlikely pairings.

Ashley Roberts was seen in London wearing a cropped polo exposing her toned tummy.

The television presenter styled her shirt with cobalt blue cargos and accessorized her look with black pointed pumps and a mini croc handbag.

No longer reserved for athletes, an influencer in Copenhagen styled her long-sleeve crop top with a micro mini plaid skirt and high heels, for a very flirty look.

Streetstyle stars in Paris are pairing their loafers with Bermuda shorts, metallic dresses and everything in between

Loafers

Preppy fashion places a strong emphasis on high-quality materials and craftsmanship, and that includes footwear.

Loafers align with these values and they pair well with preppy attire – both casual and dressy.

Blake Lively was out and about in New York City recently with bff Taylor Swift wearing loafers by sustainable, luxury footwear brand, NOMASEI.

Unlike traditional loafers that are typically designed in neutral colors to blend with classic attire, Blake color coordinated her tri-toned shoes with a red and white ensemble.

Streetstyle stars in Paris are contrasting the collegiate vibe of their loafers wearing them with Bermuda shorts, metallic dresses and everything in between.

Blake Lively was out and about in New York City recently wearing loafers by sustainable, luxury footwear brand, NOMASEI

Gigi Hadid styles her button down shirts in a more casual way, for a laid-back, contemporary look

Crisp white button down shirts are considered timeless and traditional in preppy fashion. Taylor Swift gave hers a cool girl spin with a mini skirt, baseball cap and Doc Martens

Button up shirt

Crisp white button down shirts are considered timeless and traditional in preppy fashion.

They are worn as standalone pieces – all buttoned up (of course!) – or layered under sweaters or blazers.

A versatile choice for various outfits, the women’s classic is a staple in Gigi Hadid’s wardrobe.

The supermodel, however, styles hers in a more casual way, for a laid-back, contemporary look.

Instead of buttoning up the entire shirt, Gigi only secures one or two buttons leaving the rest of the garment open, exposing a bit of her stomach.

She accessorizes with multiple necklaces and the season’s coolest kicks.

Olivia Palermo attended the label’s Womenswear Spring/Summer 2024 show during Paris Fashion Week wearing an all-over plaid dress that turned heads

Fashion journalist Madina Zhanuzakova was spotted on the streets of New York in a modern day school uniform by Thom Browne

Plaid

Plaid and tartan fabrics have historical ties to prep school uniforms and Ivy League fashion.

Today, brands like Zimmerman are using the bold pattern in unconventional ways.

Olivia Palermo attended the label’s Womenswear Spring/Summer 2024 show during Paris Fashion Week wearing an all-over plaid dress by the label that turned heads.

Her frock featured a strapless neckline and a built-in belt that cinched her waist.

She offset the garment’s sophistication with combat boots and a textured clutch.

Fashion journalist Madina Zhanuzakova was spotted on the streets of New York in a modern day school uniform by Thom Browne.

Her look consisted of a grey blazer tucked into a tea-length plaid skirt, paired with grey socks and red platform Mary Jane shoes.

Her of-the-moment look gets an A+!