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 Impression Faux Suede Belted Trench Coat
Fit & Features
- Washed faux suede fabric, moderate stretch
- 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
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Looking Luxe Faux Fur Cropped Jacket
Fit & Features
- Soft faux fur fabric with woven lining, no stretch
- 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
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Chic Choice Plaid Faux Suede Blazer
Fit & Features
- Plaid faux suede fabric, moderate stretch
- Lapel collar
- Long sleeves
- Dual faux front pockets
- 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
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Perfect Chic Faux Wool Trench Coat
Layer on the chic style with this classic faux wool trench coat featuring a lapel collar, long sleeves, an open front, and a long-line hem with a relaxed fit. Style with a mini dress and knee-high boots for the perfect fall and winter vibe!
Fit & Features
- Faux wool fabric, slight stretch
- Lapel collar
- Long sleeves
- Dual front pockets
- Open front
- Long-line hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06201-0488
Category Name: Preppy Aesthetic Outfits
Price: $56.90
Availability: In Stock
Available Color: CAMEL, OATMEAL, PINK, HEATHER, GRAY
Available Size: S, M, L, XS
Product Badge:- Best Seller
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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
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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
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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
- 3.5" Chunky block heel, 4.5" leg opening, 3.5" shaft height
- 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: 6, 6.5, 9
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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
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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
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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
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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
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Chic Moment Faux Leather Croc-Embossed Under the Knee Boots
Create a chic moment with under-the-knee boots that bring the drama! The faux leather boots feature a trendy faux croc-embossed pattern, pointy toe, an inner zipper closure, and a sturdy block heel. Complete look with a sweater dress!
Fit & Features
- 3.5” Block heel, 7" leg opening, 15" shaft height
- Under the knee-length
- Pointy toe
- Faux leather material
- Faux croc-embossing
- Inner zipper closure
- Runs true to size
Style Number/Barcode: 07402-1024
Category Name: Preppy Aesthetic Outfits
Price: $44.90
Availability: Out of Stock
- 3.5” Block heel, 7" leg opening, 15" shaft height
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Chic Sheer Mesh Sling-Back Stiletto Pumps
Fit & Features
- Stiletto heel
- Sheer mesh material
- Closed pointed toe
- Thin adjustable sling-back strap, buckle detail
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-5054
Category Name: Preppy Aesthetic Outfits
Price: $30.90
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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Raise The Bar Kitten Heel Mules
Raise the bar in these sleek kitten heel mules designed with a mini criss-cross buckle strap and closed pointed toe. Complete the look with a coat.
Fit & Features
- Stiletto kitten heel
- Closed pointed-toe
- Mini criss-cross straps with buckle
- Slingback strap
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-5087
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: Out of Stock
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The Modern Tortoiseshell Blue Light Eyeglasses
Fit & Features
- Oversized square-shaped frame
- Hard plastic
- Tortoiseshell pattern
- Blue light block lenses
- 100% UV protection
Style Number/Barcode: 07008-1117
Category Name: Preppy Aesthetic Outfits
Price: $9.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS
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Sleek Appeal Ribbed Knit Long Sleeve Bodysuit
Fit & Features
- Ribbed knit fabrication, double-lined
- Square neckline
- Fitted long sleeves
- Snap button closure
- Thong bottom coverage
- Runs true to size
Style Number/Barcode: 06002-1995
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: CHARCOAL, BLACK, OLIVE
Available Size: S, M, L, XL, XS
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Wildly Cute Leopard Faux Suede Sneakers
A pair of faux suede sneakers featuring a round toe, front lace-up closure, rubber gum sole, and a wildly cute leopard pattern. Perfect for styling with your everyday outfits.
Fit & Features
- Round toe
- Leopard pattern
- Faux suede material
- Front lace-up closure
- Rubber gum sole
- Runs true to size
Style Number/Barcode: 07407-0230
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: In Stock
Available Color: LEOPARD
Available Size: 5.5, 6
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Polished Glam Belted Wide Leg Pants
These high-rise knit pants will give your outfit a polished vibe. They feature a belted waist and a hip-hugging fit that flares out into the wide-leg hem. Pair with slingback heels.
Fit & Features
- Knit fabrication
- High-rise waist, back zipper and hook-eye closure
- Belted waist with metal grommets
- Front vertical seams
- Straight-leg
- Flared wide-leg hem
- Runs true to size
Style Number/Barcode: 06502-2546
Category Name: Preppy Aesthetic Outfits
Price: $42.90
Availability: In Stock
Available Color: BURGUNDY, BLACK
Available Size: XS, S, M, L
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Chic Staple Crew Neck Cropped Knit Cardigan
Bring your look together with a cropped knit cardigan that features a crew neckline, a button-down front, and fitted long sleeves. Pair with a pleated skirt and sneakers for a casual vibe!
Fit & Features
- Knit fabric with ribbed hems, plenty of stretch
- Crew neckline
- Button-down front
- Long sleeves
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-2142
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: BURGUNDY, BLACK
Available Size: XS, S, M, L
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Preppy Chic Drop Waist Pleated Corduroy Mini Skirt
Preppy and chic, this corduroy pleated mini skirt is such a trend! Pair with a crop sweater top and sneakers.
Fit & Features
- Corduroy fabrication, miminal stretch
- Drop waist design
- Back zipper with hook-eye closure
- Pleated
- Mini-length hem, A-line fit
- Runs true to size
Style Number/Barcode: 06301-0199
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: CHARCOAL, BLUSH
Available Size: S, M, L
Product Badge:- Sale
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Classically Chic Blue Light Eyeglasses
Protect your eyes while looking chic in these blue light eyeglasses with an oversized square frame and UV protection perfect for indoor or outdoor use. Pair with a shoulder bag.
Fit & Features
- Oversized square-shaped frame
- Hard plastic
- Blue light-blocking lenses
- 100% UV protection
Style Number/Barcode: 07008-1124
Category Name: Preppy Aesthetic Outfits
Price: $9.90
Availability: In Stock
Available Color: PINK
Available Size: NS
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Basic Over the Knee Socks
Style these basic over-the-knee socks with your favorite pleated skorts or denim rompers to give them a trendy finish.
Fit & Features
- Sheer knit fabrication
- Over-the-knee fit
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07306-0349
Category Name: Preppy Aesthetic Outfits
Price: $6.90
Availability: Out of Stock
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Chic And Tasteful Scrunch Mini Shoulder Bag
A faux leather mini shoulder bag featuring a scrunched top handle, magnetic closure, and a spacious interior with a pocket perfect for stashing your keys, cards, phone, and more.
Fit & Featuring
- Scrunch top handle
- Mini silhouette
- Magnetic closure
- Spacious interior with pocket
- Faux leather material
Style Number/Barcode: 07203-2043
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: Out of Stock
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Autumn Chic Faux Wool Long Belted Vest
Fit & Features
- Faux wool fabrication, minimal stretch
- Sleeveless collared neckline with lapels
- Tie-front belted waist with belt loops
- Dual side pockets
- Long length hem
- Runs true to size
Style Number/Barcode: 06201-0545
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: Out of Stock
Product Badge:- Best Seller
- Faux wool fabrication, minimal stretch