Preppy Aesthetic Outfits

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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.

  • 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: $33.97 $74.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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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: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: L, XS, S, M

  • 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: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plaid Pursuit Faux Wool Long Belted Vest

    The perfect charming plaid vest in a long length with pockets to keep your hands warm and a tie waist belt that cinches the look together. Pair with boots.

    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: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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: 07401-5109

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: 07306-0366

    Category Name: Preppy Aesthetic Outfits

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

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

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $1.97 $5.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free