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.
HomePreppy Aesthetic Outfits
Preppy Aesthetic Outfits
Product Recommendations
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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Chic Staple Faux Leather and Faux Suede Ankle Booties
A stylish staple bootie to pull your look together! The bootie features a mixed faux suede and faux leather material, a pointy toe, a tall stacked block heel, and an inner zipper closure. Complete with your favorite cardigan and high waist jeans.
Fit & Features
- 3.5” Block heel, 5" leg opening, 3" shaft height
- 50/50 faux suede and faux leather material
- Ankle-fit
- Pointy toe
- Inner zipper closure
- Runs true to size
Style Number/Barcode: 07403-1823
Category Name: Preppy Aesthetic Outfits
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Girl On The Go Platform Block Heel Loafers
These faux leather loafers feature a sleek closed design, a platform sole that elevates the style, and a block heel. Perfect for styling with a blazer for a posh look.
Fit & Features
- Block heel
- Faux leather material
- Square toe
- Closed design
- Platform sole
- Runs true to size
Style Number/Barcode: 07401-4989
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Statement Faux Leather Croc-Embossed Under the Knee Boots
Make a bold statement with faux leather under-the-knee boots that feature a trendy croc-embossed pattern, a pointy toe, and a block heel. Complete with a midi dress for the perfect office to happy hour outfit!
Fit & Features
- 3” block heel, 8" leg opening, 16" shaft height
- Faux leather material
- Croc-embossed pattern
- Pointy toe
- Runs true to size
Style Number/Barcode: 07402-1031
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Stunning Faux Patent Leather Pointy Flats
A stunning pair of patent leather flats featuring a sleek pointy toe and open sling back that gives your look a modern flare. Style with a crossbody purse.
Fit & Features
- Faux patent leather material
- Flat sole
- Pointy toe
- Open sling-back
- Black: Faux patent leather
- Wine: Faux croc-embossed print
- Runs true to size
Style Number/Barcode: 07405-0208
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Posh Play High Rise Wide Leg Trouser Pants
A pair of crepe trouser pants feature a flattering high-rise waist and wide-leg silhouette perfect for styling with heels.
Fit & Features
- Crepe fabric, no stretch
- High-rise waist
- Wide-leg silhouette
- Front button and hidden zipper closure
- Pants in size small have a 14" front rise with a 31.5" inseam
- Runs true to size
Style Number/Barcode: 06402-1443
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Staple Pointed Toe Stiletto Heels
These chic stiletto heels are a classic staple to have in your closet featuring a sleek pointed toe with a wide toe strap and a thin adjustable ankle strap with a buckle detail. The luxe fit cushioned insole has plush support foam for comfortable and confident wear.
Fit & Features
- Stiletto heel
- Faux nubuck material
- Open pointed toe, wide toe strap
- Thin adjustable heel strap with buckle detail
- Closed back
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-5072
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Layers Snake Chain Necklace
Bling it up with the sleek layers snake chain necklace in gold. This two-row stunner with an adjustable clasp is perfect for any occasion, from meetings to happy hours.
Fit & Features
- Two-row snake chain design
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-2025
Category Name: Preppy Aesthetic Outfits
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Secret Lock Pendant Charm Necklace
Fit & Features
- Single-row flat chain-link
- Lock pendant charm
- Toggle closure
Style Number/Barcode: 07002-2030
Category Name: Preppy Aesthetic Outfits
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Knot Stud Earrings
Fit & Features
- Knot stud design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2230
Category Name: Preppy Aesthetic Outfits
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Graceful Radiance Rhinestone Cross Pendant Necklace
Fit & Features
- Chunky chain-link chain
- Two rhinestone embellished cross pendants
- Lobster clasp closure
Style Number/Barcode: 07002-1992
Category Name: Preppy Aesthetic Outfits
Price: $10.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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Minimal Glam Three-Pack Earrings Set
Fit & Features
- Multipack includes three pairs of earrings
- 1 textured open-hoop earring
- 1 sleek open-hoop earring
- 1 square-shaped open hoop earring
- Post-back closure
Earrings are final sale and may not be returned or exchanged.Style Number/Barcode: 07001-2199
Category Name: Preppy Aesthetic Outfits
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Retro Pleated Plaid Skort
Dare to be different in this pleated plaid skort. With a high-rise waist, mini button accents, and hidden shorts, it's the perfect blend of chic and playful for your next adventure.
Fit & Features
- Woven-knit fabrication
- High-rise waist
- Mini button accents at the waist, side zipper closure
- Plaid print
- Pleated mini skirt overlay
- Hidden shorts
- Runs true to size
Style Number/Barcode: 06403-1080
Category Name: Preppy Aesthetic Outfits
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Acrylic Square Hoop Earrings
Fit & Features
- Square shape
- Acrylic design with gold-tone coated brass
- Omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2195
Category Name: Preppy Aesthetic Outfits
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Subtle Shine Three-Pack Earrings Multipack
Fit & Features
- Multipack includes three pairs of earrings
- 1 knot design with rhinestone at center earring
- 1 interlocking hoops earring
- 1 rhinestone door knocker earring
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2226
Category Name: Preppy Aesthetic Outfits
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Bliss Layered Cross Charm Necklace
Fit & Features
- Multi-layered dainty chain design
- Coin charm with rhinestone heart at center
- Rhinestone cross charm
- Lobster clasp closure
Style Number/Barcode: 07002-2027
Category Name: Preppy Aesthetic Outfits
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Statement Multi Ring Pack
Fit & Features
- Multipack includes four rings
- Chunky geometric designs
Style Number/Barcode: 07004-0435
Category Name: Preppy Aesthetic Outfits
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Layered Radiance Rhinestone Necklace
Elevate your style with the layered radiance rhinestone necklace. Triple-row design and rhinestone charm make it perfect for meetings, happy hours, and dates.
Fit & Features
- Triple-row layered design
- Flat metal design
- Rhinestone stud
- Lobster clasp closure
Style Number/Barcode: 07002-2019
Category Name: Preppy Aesthetic Outfits
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boldy Layered Metal And Tortoiseshell Bangle Multipack
Fit & Features
- Multipack includes six bangle bracelets
- Mix of metal and tortoiseshell patterns
- Variety of sleek and chunky bands
Style Number/Barcode: 07003-0629
Category Name: Preppy Aesthetic Outfits
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Confidence Textured Hoop Earrings
Fit & Features
- Open-hoop
- Textured bubble pattern
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2212
Category Name: Preppy Aesthetic Outfits
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Six-Pack Rhinestone Studs And Hoop Earrings Set
Fit & Features
- Multipack includes six pairs of earrings
- 3 pairs of various hoop designs
- 2 pairs of rhinestone studs
- 1 pair geometric stud
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2310
Category Name: Preppy Aesthetic Outfits
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brat Script Dainty Chain Necklace
Fit & Features
- Dainty chainlink
- Mini star charms
- "Brat" script pendant
- Lobster clasp closure
Style Number/Barcode: 07002-2073
Category Name: Preppy Aesthetic Outfits
Price: $8.90
Availability: Out of Stock
Product Badge:- Ships Free
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Roaring Glam Textured Lion Charm Earrings
Fit & Features
- Linear drop design
- Textured oval-shaped coin charms
- Lion design engraved
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2219
Category Name: Preppy Aesthetic Outfits
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Cozy Ribbed Knit Long Sleeve Top
Fit & Features
- Ribbed knit fabric
- V-neck and back
- Back bar strap
- Long dolman sleeves
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06005-2146
Category Name: Preppy Aesthetic Outfits
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Casual Square Neck Cropped Tank Top
Shop Matching Bottoms: Keep It Casual Pleated Mini Skort
Fit & Features
- Woven lined fabric
- Square neckline with contrast peeking trim
- Tank shoulder straps
- Chest pockets
- Front hook-eye closures
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2697
Category Name: Preppy Aesthetic Outfits
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free