15 Preppy Outfit Ideas to Elevate Your Wardrobe

The preppy style has evolved far beyond its traditional roots, incorporating modern elements while maintaining its polished essence. Whether you’re heading to brunch, the office, or a casual weekend outing, these fresh takes on preppy fashion will help you create sophisticated looks that feel current and stylish. Here’s a curated selection of preppy outfit ideas that blend classic elements with contemporary flair.

Pleated Tennis Skirt with Oversized Sweater Vest

The classic tennis skirt gets a modern upgrade when paired with an oversized sweater vest.

Layer a crisp white button-down underneath for that quintessential prep school vibe.

Complete the look with leather loafers and ankle socks for a refined finish.

Add a structured mini bag to keep things current.

Tailored Bermuda Shorts with Striped Blazer

Bermuda shorts in a tailored cut offer a sophisticated take on summer prep.

Top with a striped blazer for a nautical-inspired touch.

Layer over a simple silk camisole to keep the look elevated.

White leather sneakers add a contemporary sporty element.

Argyle Sweater Dress with Knee-High Boots

An argyle sweater dress combines comfort with classic prep style.

Choose a midi length for versatility and modern appeal.

Style with knee-high leather boots for a sophisticated edge.

Add minimal gold jewelry to complete the look.

Wide-Leg Khakis with Cropped Cable Knit

Update classic khakis by choosing a wide-leg, high-waisted cut.

Pair with a cropped cable knit sweater for proportion play.

Add a leather belt to define the waist.

White oxfords keep the look traditionally preppy.

Plaid Mini Dress with Turtleneck Layer

Layer a fitted turtleneck under a plaid mini dress for warmth and style.

Black tights create a sleek silhouette.

Chunky loafers add modern edge to the classic look.

A leather crossbody bag keeps things practical.

Cropped Tweed Jacket with High-Rise Jeans

A cropped tweed jacket adds texture and sophistication.

Pair with high-rise straight-leg jeans for a casual twist.

Keep the underlayer simple with a white t-shirt.

Pearl accessories maintain the preppy aesthetic.

Rugby Shirt with Leather Midi Skirt

Contrast a traditional rugby shirt with a leather midi skirt.

The unexpected combination creates modern prep appeal.

White sneakers keep the look casual and comfortable.

Add a structured tote for polish.

Pinstripe Jumpsuit with Penny Loafers

A pinstripe jumpsuit offers a one-and-done preppy solution.

Layer with a cream cardigan for extra warmth.

Classic penny loafers ground the look.

Keep accessories minimal with pearl studs and a leather watch.

Cable Knit Vest and Silk Midi Skirt

Layer a cable knit vest over a crisp button-down shirt.

The silk midi skirt adds unexpected luxury to the prep aesthetic.

Slingback flats offer sophisticated comfort.

A delicate pendant necklace completes the ensemble.

Windowpane Blazer with Leather Shorts

A windowpane blazer adds visual interest to the outfit.

Leather shorts create an unexpected modern twist.

Layer with a turtleneck for sophistication.

Ankle boots add edge to the preppy look.

Polo Dress with Statement Belt

Choose a polo dress in a modern midi length.

Define the waist with a statement leather belt.

White ankle boots add contemporary flair.

Accessorize with oversized sunglasses for polish.

Plaid Pants with Cashmere Hoodie

Mix traditional plaid pants with a luxe cashmere hoodie.

The casual-meets-polished combination feels fresh and modern.

Clean white sneakers keep things casual.

A canvas tote adds functionality.

Sweater Vest Dress with Combat Boots

A sweater vest dress offers a modern take on collegiate style.

Combat boots add unexpected edge.

Layer gold necklaces for personality.

A leather shoulder bag maintains sophistication.

Corduroy Blazer with Tennis Shorts

Mix textures with a corduroy blazer over tennis shorts.

Layer with a fitted turtleneck for warmth.

Clean white sneakers maintain the sporty prep vibe.

Tortoise shell accessories add classic appeal.

Varsity Cardigan with Silk Pants

A varsity cardigan gets elevated with silk wide-leg pants.

Keep the silhouette flowing and elegant.

Pointed-toe flats add sophistication.

Pearl drop earrings complete the refined prep look.