Preppy Aesthetic Outfits
Achieve the perfect preppy aesthetic with these on-trend outfit ideas. Opt for sweaters with varsity stripes or collegiate graphic tees, and pair them with mini pleated skirt or A-line skorts for a cute and classic prep look. Top it off with a varsity or bomber jacket for instant style points, or swap in denim jeans for a laid-back vibe. Explore the full collection of preppy essentials to help add a fun twist to your outfit lineup.
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Preppy Aesthetic Outfits: Chic & Trendy Looks for 2025
Get ready to embrace classic style with a fresh twist—preppy aesthetic outfits are making waves in 2025! Whether you're channeling timeless sophistication or adding a modern edge, Windsor has all the must-have pieces to perfect your look. Explore smoothing bodysuits, pleated skirts, structured blazers, and lightweight cardigans with chic letter detailing. From brunch to the boardroom, these polished styles are effortlessly on-trend.
Looking for everyday elegance? Complete your outfit with trendy sweaters layered over collared tops or pair cute shorts with structured skorts featuring buckle or strap details. For casual yet put-together vibes, mix essential basic tops with sleek blazers or must-have jackets that define the preppy look.
Elevate your footwear game with flats and sneakers that balance comfort and style, or go for polished booties to refine your outfit. Accessorize with preppy handbags, sunglasses, and timeless jewelry to bring your look together.
Heading on vacation? Keep it classic with breezy preppy resort wear, including relaxed linen shorts, chic wrap dresses, and tailored layers. For a night out, preppy cocktail attire blends sophistication with modern glam—think pleated mini skirts, sleek bodysuits, and statement accessories.
Shop online, in-app, or visit one of Windsor’s 350+ stores across the U.S. and Canada to curate your ultimate 2025 preppy looks with effortlessly chic pieces for every occasion.
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Floral Charm Cropped Cardigan Knit Sweater
Fit & Features
- Knit fabric with moderate stretch
- V-neckline
- Long sleeves, ribbed cuffs
- Floral accented buttons
- Cropped ribbed hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-2226
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Charm Plaid Trench Coat
Shop Matching Bottoms: Classic Charm Plaid Wrap Skort
Fit & Features
- Faux wool fabrication with smooth woven lining, no stretch
- Plaid pattern
- Collared neckline, double-breasted button closure
- Long sleeves with buttoned straps
- Lined slant pockets
- Long length hem
- Runs true to size
Style Number/Barcode: 06201-0507
Category Name: Preppy Aesthetic Outfits
Price: $33.97 $74.90
On Sale: Yes
Availability: Out of Stock
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Preppy Appeal Pleated Plaid Skort
Fit & Features
- Woven knit fabrication
- High-rise waist
- Checkered plaid pattern
- Double buckle accent at waist
- Pleated mini skirt overlay
- Hidden shorts
- Runs true to size
Style Number/Barcode: 06503-1251
Category Name: Preppy Aesthetic Outfits
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
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Chic Spirit Faux Wool Varsity Jacket
Fit & Features
- Faux wool fabric with woven lining, ribbed knit hems, contrast faux leather long sleeves
- Colorblock design, striped trim on collar, cuffs, and hem
- Collared neckline
- Snap button front closures
- Lined side pockets
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-2060
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Winter Slay Turtleneck Long Sleeve Bodysuit
Fit & Features
- Ribbed knit fabric, plenty of stretch
- Turtleneck
- Long fitted sleeves
- Thong-cut bottom, dual snap-button closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2087
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Comfy Chic Knit V-neck Pullover Sweater
Fit & Features
- Knit fabric with plenty of stretch
- Ribbed hems
- V-neckline
- Long sleeves
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-2245
Category Name: Preppy Aesthetic Outfits
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
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Chic Staple Oversized Blazer
Fit & Features
- Stretchy woven-knit fabrication
- Collared neckline
- Single-button front closure
- Long sleeves with multi-button cuff accent
- Front pockets with top flap closure
- Mid-hem length
- Oversized fit
Style Number/Barcode: 06204-2010
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XL
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Adorable Trendsetter Pleated Mini Skort
Fit & Features
- Woven fabric, minimal stretch
- High-rise waist, hidden side zipper closure
- Skinny belted design
- Mini-length pleated overlay, A-line silhouette
- Fitted shorts
- Skort in size small has a 7" front rise with a 1.5" inseam
- Runs true to size
Style Number/Barcode: 06401-0739
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: IVORY
Available Size: L
- Woven fabric, minimal stretch
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Cozy Staple Ribbed Knit Pullover Sweater
Fit & Features
- Ribbed knit fabrication
- Collared zipper neckline
- Long sleeves
- Mid-length hem
- Oversized fit
Style Number/Barcode: 06005-2249
Category Name: Preppy Aesthetic Outfits
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam It Up Faux Leather Skort
Fit & Features
- Faux leather fabrication
- High-rise waist
- Dual side slits
- Mini skirt overlay, hidden shorts
- Runs true to size
Style Number/Barcode: 06403-1058
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Polished Cozy Houndstooth Eyelash Knit Cardigan
Fit & Features
- Soft eyelash knit fabric with moderate stretch, ribbed hems
- Houndstooth pattern
- V-neckline
- Button-down front
- Long sleeves
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06005-000001
Category Name: Preppy Aesthetic Outfits
Price: $17.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Sale
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Corduroy Chic Mid-Rise Bubble Skirt
Fit & Features
- Corduroy fabrication
- High-rise waist, hidden side zipper and hook-eye closure
- Mini length
- Bubble hem design
- Runs true to size
Style Number/Barcode: 06301-0203
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: TAN
Available Size: S, M, L
Product Badge:- Sale
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Sleek And Snug Ribbed Knit Sweater Top
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Collared neckline
- Zipper front closure
- Long fitted sleeves
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06005-2250
Category Name: Preppy Aesthetic Outfits
Price: $11.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxe Impression Saddle Shoulder Bag
Fit & Features
- Faux patent leather material
- Saddle-shaped body
- Foldover closure
- Detachable faux leather shoulder strap
Style Number/Barcode: 07203-2074
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: Out of Stock
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Trendy Staple Asymmetric Shoulder Bag
Fit & Features
- Pebbled faux leather material
- Asymmetric design
- Top zipper closure
- Short shoulder strap, studded details
Style Number/Barcode: 07203-2067
Category Name: Preppy Aesthetic Outfits
Price: $25.90
Availability: Out of Stock
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Adorable Look Plaid Print Strapless Skater Dress
Adorably chic will be your vibe in this woven skater dress designed with a classic plaid print. It features a strapless subtle sweetheart neckline, a drop waist, and a short pleated skater silhouette for that cute flair.
Fit & Features
- Plaid printed woven fabric
- Strapless sweetheart neckline
- Back zipper closure
- Drop waist
- Mini-length pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5925
Category Name: Preppy Aesthetic Outfits
Price: $46.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Trendsetter Pleated Denim Cargo Mini Skort
This denim mini skort features a high-rise fit, a trendy drop waist design, cargo side pockets, and a short pleated overlay with fitted shorts for coverage. Style with a cropped sweater and boots for the perfect fall 'fit!
Fit & Features
- Cotton-blend denim fabric, minimal stretch
- High-rise fit with belt loops
- Back zipper with hook-eye closure
- Drop waist design, dual cargo side pockets
- Mini-length pleated overlay, fitted shorts
- Skort in size small has a 7.5" front rise with a 2" inseam
- Runs true to size
Style Number/Barcode: 06603-0419
Category Name: Preppy Aesthetic Outfits
Price: $13.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: KHAKI
Available Size: S, M
Product Badge:- Sale
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Sporty Trend Chunky Sneakers
Hit the courts in these sporty chunky sneakers for a trendy look!
Fit & Features
- Round toe
- Faux leather accented design
- Lace-up front
- Chunky sole
- Comfortable footbed
- Runs true to size
Style Number/Barcode: 07407-0245
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: BEIGE, SILVER, GREEN
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Sleek Impression Belted Straight-Leg Trouser Pants
These sleek belted straight-leg trousers make the perfect impression in and out of the office. Style the pants with a sleek jacket.
Fit & Features
- Crepe knit fabric, moderate stretch
- High-rise belted waist, back elasticized band
- Pleated detailing
- Dual front pockets
- Straight-leg fit
- Pants in size small have an 11" front rise with a 34" inseam
- Runs true to size
Style Number/Barcode: 06502-2544
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Iconic Moment Faux Leather Slouchy Shoulder Bag
Fit & Features
- Faux leather material
- Top handle
- Slouchy tote body
- Crinkle detailing
Style Number/Barcode: 07203-2095
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: BLACK, NUDE
Available Size: NS
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Chic Details Earring Multipack Set
Fit & Features
- Multipack includes three pairs of earrings
- One mini door knocker earring
- One double-hoop earring
- One chunky open hoop earring
- Post-back closure
Earrings are final sale and may not be returned or exchanged.Style Number/Barcode: 07001-2236
Category Name: Preppy Aesthetic Outfits
Price: $12.90
Availability: Out of Stock
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Boldly Crafted Multi Ring Pack
Fit & Features
- Multipack includes five rings
- Variety of textured and chunky metal designs
Style Number/Barcode: 07004-0437
Category Name: Preppy Aesthetic Outfits
Price: $12.90
Availability: Out of Stock
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Stack On The Luxe Ring Multipack
Fit & Features
- Multipack includes four rings
- Variety of chunky geometric designs
Style Number/Barcode: 07004-0434
Category Name: Preppy Aesthetic Outfits
Price: $10.90
Availability: Out of Stock
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Luxe Statement Watch Chain Bracelet
Fit & Features
- Watch-chain design
- Multi-row
Style Number/Barcode: 07003-0623
Category Name: Preppy Aesthetic Outfits
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Watch-chain design