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 Outfit Ideas for Women: Embrace the Trendy Preppy Aesthetic
Looking for fresh and stylish ways to update your wardrobe this fall and winter? Windsor's collection of preppy outfit ideas for women is here to inspire you. Whether you love classic stripes, chic plaids, or timeless collared tops, our selection brings the best of preppy fashion to colder days, so you can look polished and put-together even when temperatures drop.
Preppy style is all about layering, and Windsor has everything you need to master the look. Keep warm with trendy oversized sweaters, perfect for pairing with pleated skirts or wide-leg pants for a classic preppy vibe. Add a touch of flair with collared tops under cropped jackets or opt for a sophisticated longline blazer to elevate any look. For a fun twist, explore drop-waist skorts and bubble hem skirts—playful pieces that add volume and texture to your winter outfits.
Accessories are key to preppy winter style, and Windsor’s selection of preppy accessories makes it easy to finish your look. Choose from cozy faux wool jackets, trendy shackets, or playful hair bows to add a feminine touch. Slip on a pair of chic women’s flats or layer up with leg warmers for a throwback touch that’s perfect for chilly weather. Our bow details and accents on tops and dresses add a cute, preppy twist to any outfit, making your fall and winter wardrobe both cozy and stylish.
From ruffle dresses to varsity sweatshirts, Windsor has everything you need to create trendy preppy outfits that feel right at home this season. Explore our collection today and find your perfect mix of comfort and style with preppy aesthetic clothes that make every occasion special.
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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: $34.90
Availability: In Stock
Available Color: BLACK, IVORY, BROWN
Available Size: 10, 6, 6.5, 8, 8.5, 9, 5.5
Product Badge:- Sale
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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: 07401-4991
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: TAN
Available Size: 6.5, 7.5, 9
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: $25.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9
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: $16.00 $22.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, WINE
Available Size: 6, 6.5, 7.5, 5.5, 7, 8
Product Badge:- Sale
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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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Style Pop Square Toe Nubuck Stiletto Heels
Make your style pop in these heels featuring a square toe and thin straps for a sleek look finished with a stiletto heel. Perfect for elevating your everyday outfits.
Fit & Features
- 3.5" Stiletto heel
- Black is nubuck, red is patent material
- Square toe
- Thin straps, adjustable ankle strap, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-5026
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: In Stock
Available Color: BLACK, RED
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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: $28.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Sleek Layers Snake Chain Necklace
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: In Stock
Available Color: GOLD
Available Size: NS
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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: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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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: $9.90
Availability: Out of Stock
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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: $12.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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So Retro Pleated Plaid Skort
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: $39.90
Availability: In Stock
Available Color: TAUPE
Available Size: S, M, L
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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: $10.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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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: $12.90
Availability: Out of Stock
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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: In Stock
Available Color: GOLD
Available Size: NS
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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: $10.90
Availability: In Stock
Available Color: SILVER
Available Size: 7, 8
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Layered Radiance Rhinestone Necklace
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: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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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: $12.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS
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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: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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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: $12.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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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: In Stock
Available Color: SILVER, GOLD
Available Size: NS
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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: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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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: $34.90
Availability: In Stock
Available Color: BLACK, PLUM, HUNTER
Available Size: XS, S, M, L