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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Cool Chic Vibe Faux Wool Moto Jacket
Fit & Features
- Faux wool fabric with smooth woven lining, no stretch
- Lapel collar
- Asymmetric zip-front
- Long sleeves
- Dual lined front pockets
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06201-0550
Category Name: Preppy Aesthetic Outfits
Price: $54.90
Availability: In Stock
Available Color: OATMEAL
Available Size: XS, S, M, L
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Preppy Please Striped Pleated Knit Skort
A high-rise knit skort features a preppy pleated silhouette and a striped mini-length hem. Perfect for back-to-school or any casual plans.
Shop Matching Top And Sweater: Preppy Please Striped V-Neck Crop Top, Preppy Please Striped Button Crop Sweater
Fit & Features
- Stretchy knit fabric, shorts lining
- High-rise waist
- Pleated silhouette
- Striped mini-length hem
- Skort has a 9.5" front rise with a 2" inseam
- Runs true to size
Style Number/Barcode: 06503-1248
Category Name: Preppy Aesthetic Outfits
Price: $39.90
Availability: In Stock
Available Color: BLACK, NATURAL
Available Size: XS, S, M, L
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Stylish Staple Faux Suede Block Heel Booties
A staple pair of faux suede booties featuring a comfortable block heel and on-trend pointy toe. Complete the look with a chic trench coat.
Fit & Features
- Block heel
- Faux suede material
- Pointy toe
- Inner zipper closure
- Runs true to size
Style Number/Barcode: 07403-1801
Category Name: Preppy Aesthetic Outfits
Price: $17.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: 9, 10
Product Badge:- Sale
- Block heel
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Chic Girl Vibe Cable Knit Vest
Show off a chic girl vibe in this cable knit vest featuring a V-neckline, cap sleeves, stylish high-cut side slits for added movement, and the perfect relaxed fit to layer over your fave tops. Pair with a mini skirt and knee-high boots!
Fit & Features
- Cable knit fabric, moderate stretch
- V-neckline
- Cap sleeves
- High-cut side slits
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-2180
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: Out of Stock
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Preppy Impression Striped V-Neck Sweater Crop Top
Make a preppy impression in this sweater crop top featuring cozy long sleeves and a striped V-neckline. The knit fabric offers comfortable stretch and softness perfect for pairing with your favorite bottoms and boots.
Fit & Features
- Soft and stretchy knit fabric
- Long sleeves
- Striped V-neckline
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06005-2055
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: Out of Stock
Product Badge:- Sale
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Preppy Charm Pleated Knit Mini Skirt
Bring the preppy charm in this pleated knit mini skirt featuring a flattering mid-rise waist perfect for styling with a cropped cardigan.
Fit & Features
- Sweater-knit fabrication
- Mid-rise fit
- Pleats
- Mini length hem
- Runs true to size
Style Number/Barcode: 06501-1099
Category Name: Preppy Aesthetic Outfits
Price: $13.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: OFF, WHITE
Available Size: S, M, L
Product Badge:- Sale
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Sleek Design Hoop Earrings Set
This sleek three-pack earring set features two small pairs of asymmetric hoop earrings and one small pair of curved hoop earrings with a chic bar design. Style with a dainty necklace for everyday glamour!
Fit & Features
- Three-pack earrings set
- Two pairs of small asymmetric hoop earrings
- One pair of small curved hoop earrings with bar design
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2147
Category Name: Preppy Aesthetic Outfits
Price: $10.90
Availability: Out of Stock
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Sheer Appeal Mesh Socks
Fit & Features
- Sheer mesh fabrication
- Ankle-length
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: 07306-0390
Category Name: Preppy Aesthetic Outfits
Price: $2.97 $6.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, WHITE
Available Size: NS
Product Badge:- Sale
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Classic And Cozy Striped Knit Oversized Cardigan
Elevate your cozy looks with this classic striped ribbed knit cardigan designed with a chic oversized silhouette. It features a V-neckline with a button-down front, long sleeves with tapered hems, and a mid-length relaxed fit to pair with pleated mini skirts and knee-high boots.
Fit & Features
- Ribbed knit fabric, moderate stretch
- Striped pattern
- V-neckline
- Button-down front
- Long sleeves with tapered hems
- Mid-length hem
- Oversized fit
Style Number/Barcode: 06005-2211
Category Name: Preppy Aesthetic Outfits
Price: $23.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S/M, M/L
Product Badge:- Sale
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Preppy Allure Pleated Faux Leather Mini Skirt
Keep it preppy and chic with a faux leather mini skirt that features a mid-rise waist and playful pleats. Complete outfit with statement cardigan and boots!
Fit & Features
- Faux leather fabrication
- Mid-rise waist
- Pleats
- Mini length hem
- Runs true to hem
Style Number/Barcode: 06401-0710
Category Name: Preppy Aesthetic Outfits
Price: $24.90
Availability: In Stock
Available Color: WINE
Available Size: L
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Elegant Charm Faux Leather Bow Flats
Fit & Features
- Low-block heel
- Faux leather and faux suede material
- Closed pointed-toe
- Slingback strap with adjustable buckle
- Large bow accent
- Runs true to size
Style Number/Barcode: 07405-0205
Category Name: Preppy Aesthetic Outfits
Price: $24.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 8.5
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Fab Night Out Faux Leather Chain Link Handbag
Have a fab night out accessorizing with this faux leather chain link handbag perfect for keeping your essentials in something stylish. Pair with a coat.
Fit & Features
- Faux leather material
- Small rectangular body
- Top flap closure
- Chunky chain-link shoulder strap
Style Number/Barcode: 07203-2016
Category Name: Preppy Aesthetic Outfits
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classically Chic Faux Leather Envelope Wristlet
Strike a timeless impression with a faux leather wristlet that features a small envelope-shaped body, fold-over closure with metal trim, and a faux leather wrist strap. Complete your look with a long-sleeved blouse and midi skirt.
Fit & Features
- Faux leather material
- Small envelope-shaped body
- Fold-over closure, metal trim
- Faux leather wrist strap
Style Number/Barcode: 07201-0143
Category Name: Preppy Aesthetic Outfits
Price: $22.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Total Classic Envelope Crossbody Bag
A faux leather crossbody bag features a detachable chain strap for versatile wear, a front flap with trim and snap-button closure, and a spacious interior to keep cash, cards, and phone. Perfect for everyday styling.
Fit & Features
- Embossed croco pattern, faux leather material
- Detachable chain strap
- Front flap with trim, snap-button closure
- Spacious interior
Style Number/Barcode: 07203-2047
Category Name: Preppy Aesthetic Outfits
Price: $13.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pair To Perfection Metallic Lace-Up Sneakers
These metallic sneakers pair perfectly with your everyday outfits. They feature a round-toe, a lace-up front closure, and a rubber gum sole.
Fit & Features
- Round toe
- Metallic material
- Lace-up front closure
- Rubber gum sole
- Runs true to size
Style Number/Barcode: 07407-0231
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: In Stock
Available Color: SILVER
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Preppy Please Striped Button Crop Sweater
A sleeveless crop top featuring a preppy striped V-neckline, adjustable spaghetti straps for a customizable fit, and a striped crop hem. The stretchy knit fabric offers a polished look with plenty of stretch.
Shop Matching Top And Bottom: Preppy Please Striped V-Neck Crop Top, Preppy Please Striped Pleated Knit Skort
Fit & Features
- Stretchy knit fabric
- Long sleeves with striped cuffs
- Striped front trim
- Button front closures
- Striped crop hem
- Runs true to size
Style Number/Barcode: 06005-2184
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Instant Fave Faux Suede Platform Sneakers
A pair of faux suede sneakers feature a round toe, rubber gum platform sole that elevates the look, a lace-up front, and a side striped design. Perfect for everyday styling.
Fit & Features
- Faux suede material
- Round toe
- Rubber gum platform sole
- Lace-up front
- Side striped design
- Runs true to size
Style Number/Barcode: 07407-0232
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $30.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK/WHITE, BEIGE
Available Size: 8.5, 10, 5, 5.5, 6, 6.5, 7, 7.5, 8, 9
Product Badge:- Sale
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Style Game High-Rise Buckle Pleated Mini Skort
Level up your style game in this ponte mini skort this weekend! This skort features a high-rise waist with faux leather buckle accents, adding a touch of chic edginess. The pleated mini-length hem adds flirty movement, while the shorts lining ensures comfort and coverage. Complete the look in a cute graphic tee and sneakers.
Fit & Features
- Ponte knit fabric, stretchy knit shorts lining
- High-rise waist with faux leather buckle accents
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 06503-1162
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Preppy Please Striped V-Neck Crop Top
A sleeveless crop top featuring a preppy striped V-neckline, adjustable spaghetti straps for a customizable fit, and a striped crop hem. The stretchy knit fabric offers a polished look with plenty of stretch.
Shop Matching Sweater And Bottom: Preppy Please Striped Button Crop Sweater, Preppy Please Striped Pleated Knit Skort
Fit & Features
- Stretchy knit fabric
- Striped V-neckline
- Adjustable spaghetti straps
- Striped crop hem
- Runs true to size
Style Number/Barcode: 06005-2183
Category Name: Preppy Aesthetic Outfits
Price: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Adorable Style Mid Rise Button Pleated Mini Skirt
Show off your most adorable style in this pleated mini skirt perfect for weekly styling! Features a mid-rise waist with side button closures, creating a flattering A-line silhouette with a pleated mini-length hem. Complete the look in a cute short sleeve top.
Fit & Features
- Woven fabric with lining, no stretch
- Mid-rise waist, side button closures
- A-line silhouette
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 06401-0693
Category Name: Preppy Aesthetic Outfits
Price: $39.90
Availability: In Stock
Available Color: BEIGE
Available Size: XS, S, M, L
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Trendy Shades Square Sunglasses
Discover these trendy sunglasses perfect for any sunny day to keep your style on point! They feature a small square shape, tinted UV protective lenses, and comfortable arms and nose support. Complete the look with platform sneakers for a casual day out.
Fit & Features
- Small square shape
- Tinted UV protective lenses
- Comfortable arms and nose support
Style Number/Barcode: 07008-1089
Category Name: Preppy Aesthetic Outfits
Price: $9.90
Availability: Out of Stock
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Keep On Charming High-Rise Plaid Linen Skort
Made of sugar and spice, this plaid linen skort charms everywhere you go! The linen-blend fabric showcases a small plaid pattern for an adorable classic vibe. Featuring a high-rise waist and pleated skater silhouette, this mini-length skort offers both comfort and cuteness. Style with a basic crop top.
Fit & Features
- Plaid print
- Linen-blend woven fabric lined with woven shorts, no stretch
- High-rise waist
- Back zipper and hook-eye closure
- Pleated skater silhouette
- Runs true to size
Style Number/Barcode: 06303-0268
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: In Stock
Available Color: TAUPE
Available Size: S, M, L
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Style On Point Cat-Eye Sunglasses
These cat-eye sunglasses are here to make sure your style is always on point! They feature tinted lenses and a comfortable fit. Complete the look with a denim jacket and sandals!
Fit & Features
- Cat-eye silhouette
- Tinted lenses
- Comfortable fit
Style Number/Barcode: 07008-1086
Category Name: Preppy Aesthetic Outfits
Price: $9.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Chic Factor Oversized Sunglasses
Amp up the chic factor of your everyday 'fits with these sleek oversized sunglasses. They feature an oversized slightly angled design with a thin gold metal frame and nose bridge, thin gold metal arms with long cutouts, tinted lenses, and built-in nose pads for support. Pair these stylish shades with hoop earrings.
Fit & Features
- Oversized angled design
- Thin gold metal frame and nose bridge
- Thin gold metal arms with long cutouts
- Tinted lenses
- Built-in nose pads
Style Number/Barcode: 07008-1097
Category Name: Preppy Aesthetic Outfits
Price: $10.90
Availability: Out of Stock
Product Badge:- Sale