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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Keep It Casual Square Neck Cropped Tank Top
Shop Matching Bottoms: Keep It Casual Pleated Mini Skort
Fit & Features
- Woven lined fabric
- Square neckline with contrast peeking trim
- Tank shoulder straps
- Chest pockets
- Front hook-eye closures
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2697
Category Name: Preppy Aesthetic Outfits
Price: $32.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: S, M, L
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Keep It Casual Pleated Mini Skort
Shop Matching Top: Keep It Casual Square Neck Cropped Tank Top
Fit & Features
- Woven fabric
- High-rise waist, belt loops
- Hidden side zipper and hook-eye closure
- Contrast peeking trim
- Front mini-length pleated overlay, A-line silhouette
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-1082
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: S, M, L
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Sporty Chic Contrast Sneakers
Fit & Features
- Round toe
- Faux leather with faux suede contrast
- Lace-up front closure
- Rubber gum sole
- Silver features metallic contrast
- Runs true to size
Style Number/Barcode: 07407-0237
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: In Stock
Available Color: GOLD, SILVER, GREEN
Available Size: 6, 7, 8, 9, 10
Product Badge:- Sale
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Sleek Detail Three-Pack Hoop Earrings Set
Fit & Features
- Three-pack earrings set
- Triangle-shaped hoops
- Oval-shaped hoops
- Angled hoops
- Omega and post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2349
Category Name: Preppy Aesthetic Outfits
Price: $10.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
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Cozy Glam Cable Knit Long Sleeve Bolero
Fit & Features
- Cable knit fabrication
- Open-front design
- Long sleeves with a heart-shaped stitch pattern
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-2128
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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On The Move Faux Suede Long Blazer
Fit & Features
- Faux suede fabric with minimal stretch
- Lapel collar
- Long sleeves
- Side pockets
- Long hem length, back slit detail
- Runs true to size
Style Number/Barcode: 06204-1952
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: S, M, L, XS
Product Badge:- Best Seller
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Icon Era Houndstooth Woven Blazer
Shop Matching Bottoms: Icon Era Houndstooth Woven Mini Skirt
Fit & Features
- Houndstooth woven fabric, sewn-in woven lining
- Lapel collar
- Long sleeves
- Double-breasted button closure
- Front flap pockets
- Runs true to size
Style Number/Barcode: 06204-1955
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Casual Look Denim Mini Skort
Fit & Features
- Denim fabric
- High-rise waist
- Back zipper closure
- Dual short front slits
- Mini-length overlay, fitted shorts
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0427
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
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Edgy Prep Plaid Pleated Mini Skort
Fit & Features
- Plaid faux wool fabric
- Mid-rise fit, belted front
- Drop waist design
- Mini-length pleated overlay
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-1115
Category Name: Preppy Aesthetic Outfits
Price: $36.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: S, M, L
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Perfect In Plaid Drop Waist A-Line Romper
Fit & Features
- Plaid printed knit fabric
- Square neckline with mini bow detail
- Tank shoulder straps, square back
- Drop waist design
- Mini-length pleated overlay, A-line silhouette
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06503-1261
Category Name: Preppy Aesthetic Outfits
Price: $39.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: XS, S, M, L
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So Glam Chain Link Charm Bracelet
Fit & Features
- Chain-link
- Watch charm
- Heart charm
- Butterfly charm
- Ribbon charm
- Flower charm
- Lobster clasp closure
Style Number/Barcode: 07003-0635
Category Name: Preppy Aesthetic Outfits
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Desire For Chic Faux Leather Mini Bag
Fit & Features
- Faux leather material
- O-ring handle
- Zipper closure
- Mini design
Style Number/Barcode: 07203-2082
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Icon Era Houndstooth Woven Mini Skirt
Shop Matching Jacket: Icon Era Houndstooth Woven Blazer
Fit & Features
- Houndstooth woven fabric
- High-rise waist
- Back zipper closure
- Short side slit
- Mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06401-0728
Category Name: Preppy Aesthetic Outfits
Price: $26.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: XS, S, M, L