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
Buy on AmazonSCKTOO
$19
Buy on AmazonPahajim
$29
Buy on AmazonThe 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
Buy on AmazonGenuine
$11
Buy on AmazonZGR
$22
Buy on AmazonBermuda 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
Buy on Amazonwetkiss
$56
Buy on AmazonLIEBESKIND
$266
Buy on AmazonAn 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
Buy on AmazonPRETTYGARDEN
$42
Buy on AmazonMagpul
$80
Buy on AmazonUpdate 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
Buy on AmazonJS LifeStyle
$12
Buy on AmazonDREAM PAIRS
$44
Buy on AmazonLayer 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
Buy on AmazonKLHZHMX
$111
Buy on AmazonDanglianying
$35
Buy on AmazonA 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
Buy on AmazonHOCANDY
$29
Buy on AmazonKeyli
$26
Buy on AmazonContrast 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
Buy on AmazonPTHENA
$19
Buy on AmazonRockport
$79
Buy on AmazonA 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
Buy on AmazonZeagoo
$34
Buy on AmazonSaodimallsu
$13
Buy on AmazonLayer 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
Buy on Amazonhibshaby
$23
Buy on AmazonGeneric
$12
Buy on AmazonA 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
Buy on AmazonShinycome
$21
Buy on AmazonIDIFU
$45
Buy on AmazonChoose 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
Buy on AmazonChanyarn
$59
Buy on AmazonTOPASION
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
Buy on AmazonPORTER(ポーター)
$370
Buy on AmazonDr. Martens
$99
Buy on AmazonA 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
Buy on Amazonluvamia
$14
Buy on AmazonKeds
$43
Buy on AmazonMix 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
Buy on AmazonGORGLITTER
$14
Buy on AmazonCoutgo
$42
Buy on AmazonA 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.