Preppy Aesthetic Outfits

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

Preppy Aesthetic Outfits: Chic & Trendy Looks for 2025

Get ready to embrace classic style with a fresh twist—preppy aesthetic outfits are making waves in 2025! Whether you're channeling timeless sophistication or adding a modern edge, Windsor has all the must-have pieces to perfect your look. Explore smoothing bodysuits, pleated skirts, structured blazers, and lightweight cardigans with chic letter detailing. From brunch to the boardroom, these polished styles are effortlessly on-trend.

Looking for everyday elegance? Complete your outfit with trendy sweaters layered over collared tops or pair cute shorts with structured skorts featuring buckle or strap details. For casual yet put-together vibes, mix essential basic tops with sleek blazers or must-have jackets that define the preppy look.

Elevate your footwear game with flats and sneakers that balance comfort and style, or go for polished booties to refine your outfit. Accessorize with preppy handbags, sunglasses, and timeless jewelry to bring your look together.

Heading on vacation? Keep it classic with breezy preppy resort wear, including relaxed linen shorts, chic wrap dresses, and tailored layers. For a night out, preppy cocktail attire blends sophistication with modern glam—think pleated mini skirts, sleek bodysuits, and statement accessories.

Shop online, in-app, or visit one of Windsor’s 350+ stores across the U.S. and Canada to curate your ultimate 2025 preppy looks with effortlessly chic pieces for every occasion.

  • Cool Chic Vibe Faux Wool Moto Jacket

    Effortlessly cool, this faux wool moto jacket is such a vibe! Layer over a crop top and skirt.

    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: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • 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: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheer Appeal Mesh Socks

    Refresh your style in these sheer mesh socks perfect for pairing with sneakers or heels for an edgy appeal.

    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: Out of Stock

    Product Badge:
    • Sale
  • 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: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: Out of Stock

    Product Badge:
    • Ships Free
  • Elegant Charm Faux Leather Bow Flats

    Step out in these charming faux leather bow flats with an open slingback design and low-block heel for an elevated allure. Style these shoes with a purse.

    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: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: S, M

    Product Badge:
    • Part of a Set
  • 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: Out of Stock

    Product Badge:
    • Ships Free
  • 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: M

  • 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: S, M, L

    Product Badge:
    • Part of a Set
  • 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: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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

    Product Badge:
    • Ships Free
  • 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: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: Out of Stock

    Product Badge:
    • Ships Free
  • 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: In Stock

    Available Color: BLACK

    Available Size: NS