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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Plaid Perfection Faux Wool Long Coat
Layer on the chic style with this plaid long coat designed with structured faux wool fabric with a smooth woven lining. It features a classic lapel collar, long sleeves with buttoned strap accents, a double-breasted button design, and a long-line hem with a relaxed fit. Style with the matching mini skort!
Shop Matching Skort: Plaid Perfection Faux Wool Mini Skort
Fit & Features
- Plaid faux wool fabric with smooth woven lining, no stretch
- Lapel collar
- Long sleeves with buttoned straps
- Double-breasted button design
- Dual lined front pockets
- Long-line hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06201-0492
Category Name: Preppy Aesthetic Outfits
Price: $74.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L, XL
Product Badge:- Best Seller
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Trendy Status Corduroy Pleated Drop Waist Mini Skort
This trendy corduroy mini skort features a mid-rise fit with front button closures, an of-the-moment drop waist design, a short pleated A-line overlay with a side slit, and hidden fitted shorts. Style with a cable knit sweater and knee-high boots.
Fit & Features
- Corduroy fabric
- Mid-rise fit, three front button closures
- Drop waist design
- Mini-length pleated overlay, A-line fit
- Side slit
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06303-0283
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: WINE
Available Size: S, M, L
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Preppy In Plaid Belted And Pleated Skort
This preppy plaid woven skort features a high-rise belted waist and a mini-length pleated A-line overlay with fitted knit shorts for coverage. Style with a cropped cardigan and sneakers.
Fit & Features
- Plaid printed woven fabric, minimal stretch
- High-rise belted waist
- Hidden side zipper with hook-eye closure
- Mini-length pleated A-line overlay
- Fitted knit shorts
- Skort in size small has a 7" front rise with a 2" inseam
- Runs true to size
Style Number/Barcode: 06403-0515
Category Name: Preppy Aesthetic Outfits
Price: $26.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
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Totally Fab Belted Plaid Pleated Micro Skort
A fab plaid pleated micro mini skort that'll give your outfit a preppy look. Pair with a cardigan and boots.
Fit & Features
- Woven knit fabrication
- Belted waist accent
- Pleated mini skirt overlay
- Hidden shorts
- Plaid
- Skort in size small has a 6" front rise with a 2" inseam
- Runs true to size
Style Number/Barcode: 06403-0560
Category Name: Preppy Aesthetic Outfits
Price: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XL
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Chic Statement Faux Suede Knee-High Boots
Chic and of the moment, these faux suede boots have a knee-high design perfect for pairing with mini and midi dresses. They feature a pointed toe, a partial inner zipper closure, and a sturdy stacked block heel.
Fit & Features
- 3.5" Stacked block heel, 8" leg opening, 11" shaft height
- Faux microsuede material
- Knee-high
- Pointed toe
- Partial inner zipper closure
- Runs true to size
Style Number/Barcode: 07402-1054
Category Name: Preppy Aesthetic Outfits
Price: $46.90
Availability: In Stock
Available Color: BLACK, IVORY, BROWN
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Classic And Chic Wide-Leg Trouser Pants
These classic and chic ponte knit trouser pants feature a high-rise elasticized waist with a hip-hugging fit and a wide-leg hem. The vertical seam running down the front of each leg will create a flattering silhouette you'll love.
Fit & Features
- Ponte knit fabric with moderate stretch
- High-rise elasticized waist
- Vertical front seams
- Hip-hugging fit
- Wide-leg silhouette
- Pants in size small have an 11" front rise with a 31" inseam
- Runs true to size
Style Number/Barcode: 06502-2568
Category Name: Preppy Aesthetic Outfits
Price: $35.90
Availability: In Stock
Available Color: IVORY, BLACK
Available Size: XS, S, M, L
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Back to Basics Knit Ankle Booties
Bring your look back to basics with a smooth knit bootie to compliment your style staples! The booties feature an above-the-ankle fit, a pointy toe, and a sturdy block heel. Complete with a cardigan and high waist jeans!
Fit & Features
- 3.5" Block heel, 4" leg opening, 6" shaft height
- Smooth knit material
- Pointy toe
- Above-the-ankle fit
- Runs true to size
Style Number/Barcode: 07403-1794
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
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Adorable Flair Plaid Pleated Drop Waist Mini Skort
This adorable plaid woven mini skort features a mid-rise fit, a trendy drop waist design, and a short pleated A-line silhouette layered over fitted shorts. Style with a cozy sweater and knee-high boots.
Fit & Features
- Plaid woven fabric
- Mid-rise fit
- Drop waist design, side zipper closure
- Mini-length pleated overlay, A-line fit
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-0754
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Made For Struttin' Basic Faux Leather Booties
These basic faux leather booties were made for struttin'! They feature a pointed toe, an inner zipper closure, and a sleek block heel that elevates the style. Complete the look in a chic blazer.
Fit & Features
- 3.5" Block heel
- Pointed toe
- Inner zipper closure
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1787
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: 6, 6.5, 7, 8, 8.5, 9, 10
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City Chic Faux Leather Pleated Mini Skirt
Uncover a chic look for trips to the city in this faux leather pleated mini skirt with a trendy belted waist that makes a statement. Pair with a cropped jacket.
Fit & Features
- Faux leather fabrication
- Belted waist with large metal buckle
- Hidden side zipper and hook-eye closure
- Pleats
- Mini length hem
- Runs true to size
Style Number/Barcode: 06401-0703
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Plaid Pursuit Faux Wool Long Belted Vest
Fit & Features
- Faux wool fabrication, no stretch
- Plaid pattern
- 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: 06201-0552
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: In Stock
Available Color: TAUPE
Available Size: S, M, L
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Darling Layer V-Neck Button Crop Cardigan
A darling crop cardigan features fitted long sleeves, a flattering V-neckline, and button-up front closures for multiple styling options. Perfect for styling with your favorite bottoms.
Fit & Features
- Rib knit fabric, moderate stretch
- Fitted long sleeves
- V-neckline
- Button-up front closures
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06005-2061
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: XS, S, M, L
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Chic Moment Bubble Hoop Earrings
Accessorize your look with these bubble hoop earrings secured with a post-back closure. Pair with a handbag.
Fit & Features
- Chunky bubble design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.Style Number/Barcode: 07001-2148
Category Name: Preppy Aesthetic Outfits
Price: $8.90
Availability: Out of Stock
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Sleek Sophistication Faux Leather Crossbody Purse
Fit & Features
- Faux leather material
- Rectangular-shaped body
- Top zipper closure
- Detachable dual short metal chain-link straps
- Detachable adjustable faux leather shoulder strap
- Woven lined interior with single zippered pocket
Style Number/Barcode: 07203-2044
Category Name: Preppy Aesthetic Outfits
Price: $11.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Chic Pointed-Toe Slingback Kitten Heels
Fit & Features
- Stiletto kitten heel
- Closed pointed-toe
- Adjustable slingback strap
- Black and Leopard: Faux microsuede
- Red: Faux patent leather
- Runs true to size
Style Number/Barcode: 07401-5111
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: In Stock
Available Color: LEOPARD
Available Size: 5.5, 6, 6.5, 7, 7.5, 8.5, 10
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The Classic Pump Stiletto Heels
Step out like a boss babe or dazzle at date night with classic pump heels that feature a closed pointy toe and a sexy stiletto heel. Complete with an LBD and blazer to take you from day to night!
Fit & Features
- Stiletto heel
- Faux suede material
- Closed pointy toe
- Runs true to size
Style Number/Barcode: 07401-5203
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: In Stock
Available Color: BLACK
Available Size: 8
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Trendy Seams Sheer Stockings
Fit & Features
- Sheer nylon fabrication
- Thigh-high design
- Center back seam
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: 07306-0367
Category Name: Preppy Aesthetic Outfits
Price: $9.90
Availability: In Stock
Available Color: WHITE
Available Size: NS
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So Poised Plaid Pleated Mini Skirt
Keep it poised in a mini skirt with a mid-rise waist, plaid pattern, and flattering pleats. Complete with an off-the-shoulder top and flats.
Fit & Features
- Plaid patterned woven fabric, no stretch
- Mid-rise waist
- Side zipper with hook-eye closure
- Pleated detailing
- Mini-length hem
- A-line fit
- Runs true to size
Style Number/Barcode: 06401-0694
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Toasty Babe Long Sleeve Rib Knit Crop Top
A long sleeve rib knit crop top boasts a scoop neckline with dual hook-eye closures and a center slit design to flaunt skin. Style with a mini skirt for going out.
Fit & Features
- Rib knit stretchy fabric
- Fitted long sleeves
- Scoop neckline
- Dual hook-eye closures
- Center slit design
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06005-2034
Category Name: Preppy Aesthetic Outfits
Price: $29.90
Availability: In Stock
Available Color: IVORY, BROWN
Available Size: S, M, L, XS
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Oh-So-Adorable Bow Detail Socks
Oh-so-adorable, these ankle-high socks feature the cutest bow-back design. Style with sneakers for a casual look or platform heels for a dressy chic vibe!
Fit & Features
- Knit fabric with moderate stretch
- Ankle-high length
- Satin-like bow-back design
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: 07306-0358
Category Name: Preppy Aesthetic Outfits
Price: $5.90
Availability: Out of Stock
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Luxe Allure Pointed-Toe Faux Leather Flats
Luxe and alluring, these pointed-toe faux leather flats will give your look a polished vibe. Pair with trouser pants.
Fit & Features
- Flat sole
- Faux leather material
- Pointed-toe
- Chain-link metal accent
- Slingback strap
- Faux leather material
- Runs true to size
Style Number/Barcode: 07405-0220
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $20.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: 6, 7.5, 5.5, 6.5, 7, 8.5
Product Badge:- Sale
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Elevated Muse Crepe Longline Blazer
Layer on this longline blazer to elevate your fall looks featuring a lapel collar, three-quarter-length sleeves with cuffed hems, side pockets, and a chic relaxed silhouette. The crepe fabric offers a structured fit with moderate stretch.
Fit & Features
- Crepe knit fabric with moderate stretch
- Lapel collar
- Three-quarter-length sleeves, cuffed hems
- Dual side pockets
- Long-line hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06202-0502
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: MOCHA, BLACK
Available Size: S, M, L
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Preppy Aesthetic Collared Crew Neck Sweater
Create that preppy aesthetic with this knit sweater featuring a woven collared design and crew neckline, long sleeves, and a mid-length hem with a woven trim for that chic layered look. Style with a plaid skirt and sneakers!
Fit & Features
- Ribbed sweater knit fabric, moderate stretch
- Woven collared design
- Crew neckline
- Long sleeves
- Mid-length hem, woven trim
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-2044
Category Name: Preppy Aesthetic Outfits
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Perfectly Cozy Chunky Knit Cardigan
This perfectly cozy cardigan is designed with a chunky ribbed knit fabric for that comfy and chic vibe. It features a V-neckline, a complete button-down front, long dolman-style sleeves, and a mid-length hem with a relaxed fit.
Fit & Features
- Chunky ribbed knit fabric, moderate stretch
- V-neckline
- Complete button-down front
- Long dolman sleeves
- Mid-length hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06005-2209
Category Name: Preppy Aesthetic Outfits
Price: $54.90
Availability: Out of Stock