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

Lueluoye

$32

★★★★ 4.5 (647 reviews)
Buy on Amazon

SCKTOO

$19

★★★★ 4.1 (7,832 reviews)
Buy on Amazon

Pahajim

$29

★★★★ 4 (2,803 reviews)
Buy on Amazon

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

siliteelon

$25

★★★★ 4.2 (139 reviews)
Buy on Amazon

Genuine

$11

★★ 2.5 (2 reviews)
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ZGR

$22

★★★★ 4.2 (230 reviews)
Buy on Amazon

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

RQP

$27

★★★★ 4.5 (41 reviews)
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wetkiss

$56

★★★★ 4.1 (50 reviews)
Buy on Amazon

LIEBESKIND

$266

★★★★★ 5 (2 reviews)
Buy on Amazon

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

Cyparel

$36

★★★★ 4.1 (217 reviews)
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PRETTYGARDEN

$42

★★★★ 4.4 (245 reviews)
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Magpul

$80

★★★★ 4.7 (479 reviews)
Buy on Amazon

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

Milumia

$34

★★★ 3.5 (39 reviews)
Buy on Amazon

JS LifeStyle

$12

★★★★ 4.2 (50 reviews)
Buy on Amazon

DREAM PAIRS

$44

★★★★ 4.4 (982 reviews)
Buy on Amazon

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

KDF

$32

★★★★ 4.3 (193 reviews)
Buy on Amazon

KLHZHMX

$111

N/A (0 reviews)
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Danglianying

$35

★★★★ 4.3 (334 reviews)
Buy on Amazon

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

UKTZFTBMTS

$34

N/A (0 reviews)
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HOCANDY

$29

★★★★ 4.7 (4 reviews)
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Keyli

$26

★★★★ 4.4 (604 reviews)
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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

YEXPINE

$44

★★★★ 4.1 (9 reviews)
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PTHENA

$19

★★★★ 4.3 (85 reviews)
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Rockport

$79

★★★★ 4.3 (4,775 reviews)
Buy on Amazon

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

Lueluoye

$32

★★★★ 4.5 (647 reviews)
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Zeagoo

$34

★★★★ 4.2 (2,360 reviews)
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Saodimallsu

$13

★★★★ 4 (71 reviews)
Buy on Amazon

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

Grlasen

$58

★★★★ 4 (945 reviews)
Buy on Amazon

hibshaby

$23

★★★★ 4.1 (548 reviews)
Buy on Amazon

Generic

$12

N/A (0 reviews)
Buy on Amazon

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

Meetrendi

$21

★★★★ 4.6 (20 reviews)
Buy on Amazon

Shinycome

$21

N/A (0 reviews)
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IDIFU

$45

★★★★ 4.2 (457 reviews)
Buy on Amazon

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

Allegra K

$34

★★★ 3.8 (772 reviews)
Buy on Amazon

Chanyarn

$59

★★★★ 4.5 (38 reviews)
Buy on Amazon

TOPASION

$8

★★★★ 4.6 (926 reviews)
Buy on Amazon

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

YM YOUMU

$16

N/A (0 reviews)
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PORTER(ポーター)

$370

★★★★★ 5 (2 reviews)
Buy on Amazon

Dr. Martens

$99

★★★★ 4.7 (3,923 reviews)
Buy on Amazon

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

RICHTRUE

$49

★★★ 3.9 (13 reviews)
Buy on Amazon

luvamia

$14

★★★★ 4.8 (6 reviews)
Buy on Amazon

Keds

$43

★★★★ 4.2 (1,071 reviews)
Buy on Amazon

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

AUTOMET

$38

★★★★ 4 (463 reviews)
Buy on Amazon

GORGLITTER

$14

N/A (0 reviews)
Buy on Amazon

Coutgo

$42

★★★★ 4.2 (109 reviews)
Buy on Amazon

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.

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