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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Floral Charm Cropped Cardigan Knit Sweater
Fit & Features
- Knit fabrication
- V-neckline
- Long sleeves, ribbed cuff
- Floral accented buttons
- Cropped ribbed hem
- Runs true to size
Style Number/Barcode: 06005-2226
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Classic Charm Plaid Trench Coat
Fit & Features
- Faux wool fabrication
- Collared neckline
- Double-breasted button closure
- Long sleeves
- Slant pockets
- Plaid pattern
- Long length hem
- Runs true to size
Shop Matching Skort: Classic Charm Plaid Wrap Skort
Style Number/Barcode: 06201-0507
Category Name: Preppy Aesthetic Outfits
Price: $74.90
Availability: In Stock
Available Color: GRAY
Available Size: S, M, L, XL
Product Badge:- New Arrival
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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: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XL
Product Badge:- New Arrival
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Cozy Factor Ribbed Knit Off-The-Shoulder Sweater
Fit & Features
- Ribbed knit fabric with moderate stretch
- Off-the-shoulder neckline, fold-over design
- Long sleeves
- Oversized fit
Style Number/Barcode: 06005-2152
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: In Stock
Available Color: CHARCOAL, IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Adorably Sleek Faux Leather Pleated Mini Skort
Fit & Features
- Coated faux leather fabric
- High-rise waist, belt loops
- Front button closure
- Front zippered accents
- Drop waist
- Mini-length pleated overlay, fitted shorts
- Runs true to size
Style Number/Barcode: 06403-1071
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Cute And Comfy Zip-Front Cropped Knit Hoodie
Fit & Features
- Sweater knit fabric with plenty of stretch
- Drawstring hooded neckline
- Zip-front
- Long sleeves with ribbed hems
- Fitted cropped ribbed hem
- Runs true to size
Style Number/Barcode: 06005-2126
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Cozy Staple Long Knit Duster Cardigan
Fit & Features
- Soft knit fabric with plenty of stretch
- Ribbed hems
- Long sleeves
- Dual front pockets
- Long length
- Oversized fit
Style Number/Barcode: 06005-2103
Category Name: Preppy Aesthetic Outfits
Price: $46.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Chic Impression Faux Suede Belted Trench Coat
Fit & Features
- Washed faux suede fabric
- Lapel collar
- Long sleeves
- Tie-front belt
- Long-length hem
- Runs true to size
Style Number/Barcode: 06204-1922
Category Name: Preppy Aesthetic Outfits
Price: $52.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
Product Badge:- New Arrival
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Cool-Girl Edge Platform Block Heel Booties
Add some cool-girl edge to your cold-weather 'fits with these faux suede platform booties designed with a ribbed knit elastic gore and ankle. They feature a round toe, a platform lug sole, and a chunky block heel.
Fit & Features
- Chunky block heel, lug sole
- Faux microsuede material
- Ankle-high
- Ribbed knit elastic gore and ankle, back pull tab
- Round toe
- Platform lug sole
- Runs true to size
Style Number/Barcode: 07401-5118
Category Name: Preppy Aesthetic Outfits
Price: $40.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Sleek Icon Faux Leather Long Belted Vest
Fit & Features
- Smooth faux leather fabric with nylon lining, no stretch
- Sleeveless lapel collared neckline
- Open front
- Tie-front belted waist
- Dual front lined pockets
- Long length, relaxed fit
- Runs true to size
Style Number/Barcode: 06204-1944
Category Name: Preppy Aesthetic Outfits
Price: $52.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Classic Charm Plaid Wrap Skort
Fit & Features
- Faux wool fabrication
- Mid-rise waist
- Mini skirt wrap overlay
- Hidden shorts
- Plaid pattern
- Runs true to size
Shop Matching Trench Coat: Classic Charm Plaid Trench CoatStyle Number/Barcode: 06403-1065
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Chic Choice Plaid Faux Suede Blazer
Fit & Features
- Plaid faux suede fabric
- Lapel collar
- Long sleeves
- Long-length hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-1947
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: In Stock
Available Color: TAUPE
Available Size: S, M, L, XL
Product Badge:- New Arrival
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Here To Slay Under-The-Knee Block Heel Boots
Fit & Features
- Block heel
- Half faux leather, half spandex material
- Under-the-knee height
- Square toe
- Complete inner zipper closure
- Runs true to size
Style Number/Barcode: 07402-1079
Category Name: Preppy Aesthetic Outfits
Price: $48.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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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
Available Size: NS
Product Badge:- New Arrival
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Sleek Strut Slingback Stiletto Pumps
Fit & Features
- Stiletto heel
- Slingback ankle strap, chainlink metal accent
- Closed pointed toe
- Faux patent leather material
- Runs true to size
Style Number/Barcode: 07401-5082
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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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: $34.90
Availability: In Stock
Available Color: KHAKI
Available Size: XS, S, M, L
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Sporty Trend Chunky Sneakers
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
Product Badge:- New Arrival
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Sleek Impression Belted Straight-Leg Trouser Pants
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
Product Badge:- New Arrival
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Wild Glam Leopard Print Slingback Pumps
Fit & Features
- Stiletto heel
- Closed-pointed toe
- Slingback strap, accented with chainlink detail
- Leopard print
- Faux patent leather material
- Runs true to size
Style Number/Barcode: 07401-5081
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: LEOPARD
Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge:- New Arrival
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Looking Luxe Faux Fur Cropped Jacket
Fit & Features
- Faux fur fabric
- Wide collared neckline
- Long sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06201-0539
Category Name: Preppy Aesthetic Outfits
Price: $52.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
Product Badge:- New Arrival
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Effortless Twist Metal Collar Necklace
Fit & Features
- Single-row
- Twisted metal design
- Lobster clasp closure
Style Number/Barcode: 07002-1984
Category Name: Preppy Aesthetic Outfits
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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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: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
- Watch-chain design
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Iconic Glam Half-Moon Shoulder Bag
Fit & Features
- Faux leather fabrication
- Top handle
- Top zipper closure
- Half-moon shape
- Metal hardware accents
Style Number/Barcode: 07203-2093
Category Name: Preppy Aesthetic Outfits
Price: $26.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: NS
Product Badge:- New Arrival