Preppy style continues to evolve in 2025, blending traditional collegiate aesthetics with contemporary influences. This season’s preppy trends embrace both classic elements and fresh interpretations, creating sophisticated looks perfect for autumn weather. Here are 20 refined outfit ideas that capture the essence of modern preppy dressing.
1) Plaid Blazer with Straight-Leg Trousers
[Image: Navy and burgundy plaid blazer over white button-down with gray straight-leg trousers and brown leather loafers]
Photo Credit: Ralph Lauren via ralphlauren.com
Plaid jackets strike that ideal balance between preppy and elevated, making them surprisingly versatile for day-to-night dressing. Choose heritage patterns in traditional color combinations for authentic preppy appeal.
Classic plaid blazers in wool or tweed provide structured sophistication perfect for fall weather. The pattern adds visual interest while maintaining professional appropriateness across settings.
Style with crisp white button-downs and tailored trousers. Brown leather loafers complete this timeless combination with collegiate-inspired polish that works from office to country club.
2) Cable Knit Sweater with Pleated Mini Skirt
[Image: Cream cable knit sweater with navy pleated mini skirt, knee-high socks, and penny loafers]
Photo Credit: J.Crew via jcrew.com
The basic elements include polo shirts, blazers, and cable knit sweaters with neutral/pastel tones and more of a fitted form rather than an oversized fit. Cable knits provide textural interest within classic parameters.
A outfit of a short, pleated skirt and blazer in plaid or tweed paired with a plain black or white shirt is iconic. Pleated mini skirts embody quintessential preppy femininity with collegiate charm.
Knee-high socks and penny loafers reference traditional boarding school uniforms. This youthful combination channels academic inspiration with contemporary wearability and timeless preppy appeal.
3) Oversized Blazer with Straight-Leg Jeans
[Image: Oversized navy blazer over striped rugby shirt with medium wash straight-leg jeans and white sneakers]
Photo Credit: Tommy Hilfiger via tommyhilfiger.com
Oversized blazers are a must to sport preppy style while embracing 2025’s preference for relaxed tailoring. The structured silhouette balances casual denim beautifully.
Gen Z is putting their own spin on the classic aesthetic, mixing traditional staples with streetwear influences, oversize fits and gender-fluid styling. This modern approach keeps preppy style current.
Rugby shirts underneath add authentic athletic references. White sneakers complete the contemporary preppy look that blends traditional elements with current casual comfort preferences.
4) Fair Isle Sweater with Corduroy Pants
[Image: Burgundy and cream Fair Isle sweater with brown corduroy straight-leg pants and suede desert boots]
Photo Credit: L.L.Bean via llbean.com
Fair Isle patterns represent traditional preppy knitwear with heritage appeal. Choose classic color combinations like burgundy, cream, and navy for authentic autumn sophistication.
Corduroy pants add textural richness perfect for fall weather. The casual fabric maintains comfort while the tailored cut ensures appropriate polish for preppy styling.
Suede desert boots provide relaxed elegance with seasonal appropriateness. This combination channels countryside charm with academic inspiration and comfortable autumn wearability.
5) Turtleneck Under Sweater Vest
[Image: White turtleneck under cream sweater vest with navy pleated skirt and brown oxford shoes]
Photo Credit: Brooks Brothers via brooksbrothers.com
A strong preppy wardrobe includes structured blazers, button-down shirts, pleated skirts, sweater vests, and tailored trousers. Sweater vests create sophisticated layering with academic references.
Turtlenecks underneath provide warmth and coverage while maintaining clean lines. The layering technique adds visual interest within refined preppy parameters.
Navy pleated skirts and brown oxford shoes complete this scholarly-inspired ensemble. The combination embodies traditional prep school aesthetics with contemporary wearability and timeless appeal.
6) Tartan Scarf with Neutral Basics
[Image: Camel coat over cream sweater with dark jeans and tartan scarf in red and green plaid]
Photo Credit: Barbour via barbour.com
Tartan accessories add heritage references without overwhelming neutral foundations. Choose traditional clan patterns in classic color combinations for authentic Scottish inspiration.
Camel coats provide sophisticated outerwear that coordinates beautifully with plaid accessories. The neutral tone allows patterned scarves to shine while maintaining elegant restraint.
Dark denim and cream sweaters create versatile foundations. This combination channels countryside sophistication with practical autumn warmth and timeless preppy elegance.
7) Polo Shirt with Cardigan and Chinos
[Image: Navy polo shirt under cream cardigan with khaki chinos and brown leather belt with matching loafers]
Photo Credit: Polo Ralph Lauren via ralphlauren.com
Preppy style is a fashion aesthetic inspired by the Ivy League look, characterized by clean, classic pieces such as polo shirts, blazers, and loafers. Polo shirts remain foundational to authentic preppy dressing.
Cardigans add sophisticated layering while maintaining casual comfort. Choose quality knits in complementary colors for cohesive autumn styling with traditional appeal.
Khaki chinos and brown leather accessories complete this country club-inspired ensemble. The combination embodies relaxed elegance perfect for weekend activities and casual social gatherings.
8) Tweed Jacket with Midi Skirt
[Image: Brown tweed jacket over ivory blouse with burgundy midi skirt and cognac leather ankle boots]
Photo Credit: J.Crew via jcrew.com
Tweed jackets represent traditional British tailoring with heritage craftsmanship. Choose classic weaves in autumn colors that coordinate with existing wardrobe pieces.
Midi skirts in rich colors like burgundy or forest green provide sophisticated foundations. The modest length maintains appropriateness while the tailored fit ensures polished appearance.
Cognac leather boots add warmth and texture. This combination channels English countryside elegance with academic inspiration and sophisticated autumn styling.
9) Striped Sweater with Wide-Leg Trousers
[Image: Navy and white striped sweater with cream wide-leg trousers and navy canvas sneakers with white soles]
Photo Credit: COS via cosstores.com
the 1990s welcomed low-rise jeans and nautical-inspired stripes while modern interpretations embrace higher waistlines and relaxed fits for contemporary appeal.
Wide-leg trousers provide comfortable elegance while maintaining structured polish. The flowing silhouette balances fitted striped tops beautifully for proportional harmony.
Canvas sneakers with classic styling add casual comfort. This combination embraces nautical inspiration with modern relaxed tailoring and practical autumn comfort.
10) Quilted Vest Over Button-Down
[Image: Navy quilted vest over white button-down shirt with dark wash jeans and brown leather boat shoes]
Photo Credit: Vineyard Vines via vineyardvines.com
Quilted vests add preppy layering with equestrian references. Choose classic colors like navy, hunter green, or burgundy for versatile autumn styling options.
Button-down shirts underneath provide crisp foundations while vests add warmth without bulk. This layering technique works particularly well for transitional fall weather.
Dark denim and boat shoes complete this New England-inspired ensemble. The combination embodies coastal preppy style with practical comfort and timeless collegiate appeal.
11) Argyle Sweater with Corduroy Skirt
[Image: Pink and gray argyle sweater with brown corduroy A-line skirt and brown penny loafers with tassels]
Photo Credit: Pringle of Scotland via pringlescotland.com
Argyle patterns represent traditional preppy knitwear with Scottish heritage. Choose classic color combinations in quality wool for authentic academic inspiration.
Corduroy skirts add textural richness perfect for autumn styling. The A-line silhouette provides flattering movement while maintaining appropriate coverage and polish.
Penny loafers with tassels complete this scholarly ensemble. The combination channels boarding school elegance with heritage craftsmanship and timeless preppy sophistication.
12) Blazer Over Turtleneck with Plaid Pants
[Image: Navy blazer over cream turtleneck with red and navy plaid straight-leg pants and black leather loafers]
Photo Credit: Theory via theory.com
Power blazers nip at the waist while maintaining structured sophistication perfect for modern preppy styling. The tailored silhouette provides polished foundations.
Plaid pants make statement pieces when balanced with solid blazers. Choose coordinating colors that work within existing wardrobe color schemes for maximum versatility.
Black leather loafers ground patterned bottoms with classic simplicity. This combination embraces pattern mixing with sophisticated restraint and academic inspiration.
13) Cricket Sweater with Flannel Trousers
[Image: White cricket sweater with navy and burgundy trim over gray flannel trousers with brown oxford shoes]
Photo Credit: John Smedley via johnsmedley.com
Cricket sweaters reference traditional British sporting heritage with preppy authenticity. The clean white base with colored trim creates classic academic appeal.
Gray flannel trousers provide sophisticated foundations with professional polish. The quality fabric and tailored cut ensure appropriate elegance for formal preppy occasions.
Brown oxford shoes complete this heritage-inspired ensemble. The combination embodies traditional English sporting elegance with scholarly sophistication and timeless appeal.
14) Denim Shirt with Wool Skirt
[Image: Light blue denim shirt tucked into brown wool pencil skirt with cognac leather belt and matching boots]
Photo Credit: Madewell via madewell.com
Denim shirts gain sophistication when paired with wool skirts and quality accessories. Choose lighter washes and structured fits for polished preppy styling.
Wool pencil skirts in autumn colors provide elegant foundations. The structured silhouette balances casual denim tops while maintaining appropriate preppy proportions.
Cognac leather accessories add warmth and luxury. This combination blends casual American elements with traditional preppy polish and contemporary wearability.
15) Cashmere Cardigan with Pleated Trousers
[Image: Camel cashmere cardigan over white t-shirt with navy pleated wide-leg trousers and nude leather loafers]
Photo Credit: Brunello Cucinelli via brunellocucinelli.com
Adding a pair of sneakers and a blazer to your outfit base is a classic preppy look that has really come back around this year. It says laid-back, yet pulled together while cashmere adds luxury to casual foundations.
Pleated wide-leg trousers combine traditional preppy elements with contemporary silhouettes. The flowing shape provides comfort while maintaining structured polish.
Nude leather loafers create seamless coordination. This combination embodies relaxed elegance with quality investment pieces and sophisticated autumn styling.
16) Rugby Shirt with Tweed Skirt
[Image: Burgundy and white striped rugby shirt with brown tweed A-line mini skirt and tan knee-high boots]
Photo Credit: Gant via gant.com
rugby shirts to blazers, loafers to sweater vests represent essential preppy pieces for 2025. Rugby shirts add athletic references with collegiate charm.
Tweed skirts in classic weaves provide heritage sophistication. The structured fabric and A-line silhouette create flattering proportions with traditional preppy authenticity.
Knee-high boots in tan leather add warmth and elegance. This combination channels sporting traditions with academic inspiration and sophisticated autumn styling.
17) Fair Isle Vest Over White Shirt
[Image: Navy and cream Fair Isle vest over white button-down with khaki wide-leg pants and brown leather Oxford shoes]
Photo Credit: Barbour via barbour.com
Fair Isle vests provide traditional patterning with sophisticated layering options. The classic knit patterns add visual interest while maintaining academic references.
White button-downs underneath ensure crisp foundations while vests add warmth and texture. This layering technique works particularly well for changing autumn temperatures.
Khaki wide-leg pants and brown Oxfords complete this heritage-inspired ensemble. The combination embodies countryside sophistication with scholarly elegance and timeless appeal.
18) Houndstooth Coat with Dark Jeans
[Image: Black and white houndstooth coat over cream sweater with dark skinny jeans and black ankle boots]
Photo Credit: Max Mara via maxmara.com
new-age plaid and traditional patterns like houndstooth remain central to fall 2025 preppy trends. The classic pattern provides sophisticated visual interest.
Dark skinny jeans create sleek foundations that allow patterned coats to shine. The streamlined silhouette balances voluminous outerwear beautifully.
Black ankle boots ground the outfit with modern edge. This combination blends traditional preppy patterns with contemporary silhouettes and urban sophistication.
19) Sweater Blazer with Midi Dress
[Image: Gray knit blazer over navy midi dress with brown leather belt and matching oxford shoes]
Photo Credit: Eileen Fisher via eileenfisher.com
Sweater blazers combine structured tailoring with comfortable knit fabrics. This hybrid approach embraces relaxed elegance while maintaining professional polish.
Navy midi dresses provide versatile foundations that work across seasons. The modest length and classic color ensure appropriate sophistication for various occasions.
Brown leather accessories add warmth and coordination. This combination embodies modern preppy evolution with comfortable luxury and timeless academic inspiration.
20) Layered Sweaters with Plaid Scarf
[Image: Cream turtleneck under camel crew neck sweater with dark jeans and green and navy plaid scarf]
Photo Credit: L.L.Bean via llbean.com
Layered sweaters create textural depth while providing practical warmth for autumn weather. Choose complementary neutrals for sophisticated tonal coordination.
riding boots, the top shoe trend for fall 2025 while plaid accessories add heritage references with traditional preppy authenticity and visual interest.
Dark jeans provide casual foundations while plaid scarves add pattern and color. This combination embraces cozy comfort with preppy sophistication and seasonal appropriateness.
