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.

  • Chic Impression Faux Suede Belted Trench Coat

    Make a chic impression in this faux suede belted trench coat. With a lapel collar and long sleeves, it's your go-to for effortless style. Tie it up and strut with confidence!

    Fit & Features

    • Washed faux suede fabric, moderate stretch
    • Lapel collar
    • Long sleeves
    • Tie-front belt
    • Long-length hem
    • Runs true to size

    Style Number/Barcode: 06204-1922

    Category Name: Preppy Aesthetic Outfits

    Price: $14.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Luxe Faux Fur Cropped Jacket

    Indulge in luxe in this faux fur cropped jacket perfect for creating fabulous looks!

    Fit & Features

    • Soft faux fur fabric with woven lining, no stretch
    • Wide collared neckline
    • Long sleeves
    • Cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06201-0539

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Choice Plaid Faux Suede Blazer

    A chic plaid faux suede blazer fit for a preppy girlie like you! Layer on this essential blazer in the perfect relaxed fit for comfort and a stylish look.

    Fit & Features

    • Plaid faux suede fabric, moderate stretch
    • Lapel collar
    • Long sleeves
    • Dual faux front pockets
    • Long-length hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-1947

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Chic Faux Wool Trench Coat

    Layer on the chic style with this classic faux wool trench coat featuring a lapel collar, long sleeves, an open front, and a long-line hem with a relaxed fit. Style with a mini dress and knee-high boots for the perfect fall and winter vibe!

    Fit & Features

    • Faux wool fabric, slight stretch
    • Lapel collar
    • Long sleeves
    • Dual front pockets
    • Open front
    • Long-line hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06201-0488

    Category Name: Preppy Aesthetic Outfits

    Price: $23.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Iconic Glam Half-Moon Shoulder Bag

    Carry your essentials in this iconic shoulder bag in a half-moon design with metal hardware accents for a sleek finish.

    Fit & Features

    • Faux leather fabrication
    • Top handle
    • Top zipper closure
    • Half-moon shape
    • Metal hardware accents

    Style Number/Barcode: 07203-2093

    Category Name: Preppy Aesthetic Outfits

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Comfy Zip-Front Cropped Knit Hoodie

    Fit & Features

    • Sweater knit fabric with plenty of stretch
    • Drawstring hooded neckline
    • Zip-front
    • Long sleeves with ribbed hems
    • Fitted cropped ribbed hem
    • Runs true to size

    Style Number/Barcode: 06005-2126

    Category Name: Preppy Aesthetic Outfits

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool-Girl Edge Platform Block Heel Booties

    Add some cool-girl edge to your cold-weather 'fits with these faux suede platform booties designed with a ribbed knit elastic gore and ankle. They feature a round toe, a platform lug sole, and a chunky block heel.

    Fit & Features

    • 3.5" Chunky block heel, 4.5" leg opening, 3.5" shaft height
    • Faux microsuede material
    • Ankle-high
    • Ribbed knit elastic gore and ankle, back pull tab
    • Round toe
    • Platform lug sole
    • Runs true to size

    Style Number/Barcode: 07401-5118

    Category Name: Preppy Aesthetic Outfits

    Price: $12.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Twist Metal Collar Necklace

    Fit & Features

    • Single-row
    • Twisted metal design
    • Lobster clasp closure

    Style Number/Barcode: 07002-1984

    Category Name: Preppy Aesthetic Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorably Sleek Faux Leather Pleated Mini Skort

    Get ready to slay in the adorably sleek faux leather pleated mini skort. With a high-rise waist, zippered accents, and a pleated overlay, it's your go-to for edgy vibes.

    Fit & Features

    • Coated faux leather fabric
    • High-rise waist, belt loops
    • Front button closure
    • Front zippered accents
    • Drop waist
    • Mini-length pleated overlay, fitted shorts
    • Runs true to size

    Style Number/Barcode: 06403-1071

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Sleek Icon Faux Leather Long Belted Vest

    Go sleek in this faux leather long belted vest with dual front pockets and a tie waist belt that cinches your look. Pair with boots.

    Fit & Features

    • Smooth faux leather fabric with nylon lining, no stretch
    • Sleeveless lapel collared neckline
    • Open front
    • Tie-front belted waist
    • Dual front lined pockets
    • Long length, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-1944

    Category Name: Preppy Aesthetic Outfits

    Price: $10.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Staple Long Knit Duster Cardigan

    Cozy staple long knit duster cardigan is your go-to for effortless style. With soft knit, ribbed hems, and dual pockets, it's perfect for layering up and keeping it chic.

    Fit & Features

    • Soft knit fabric with plenty of stretch
    • Ribbed hems
    • Long sleeves
    • Dual front pockets
    • Long length
    • Oversized fit

    Style Number/Barcode: 06005-2103

    Category Name: Preppy Aesthetic Outfits

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Moment Faux Leather Croc-Embossed Under the Knee Boots

    Create a chic moment with under-the-knee boots that bring the drama! The faux leather boots feature a trendy faux croc-embossed pattern, pointy toe, an inner zipper closure, and a sturdy block heel. Complete look with a sweater dress! 

    Fit & Features

    • 3.5” Block heel, 7" leg opening, 15" shaft height
    • Under the knee-length
    • Pointy toe
    • Faux leather material
    • Faux croc-embossing
    • Inner zipper closure
    • Runs true to size

    Style Number/Barcode: 07402-1024

    Category Name: Preppy Aesthetic Outfits

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Sheer Mesh Sling-Back Stiletto Pumps

    These chic slingback stiletto pumps give every outfit a modern flair with a sheer mesh design. Style with cute socks.

    Fit & Features

    • Stiletto heel
    • Sheer mesh material
    • Closed pointed toe
    • Thin adjustable sling-back strap, buckle detail
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-5054

    Category Name: Preppy Aesthetic Outfits

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raise The Bar Kitten Heel Mules

    Raise the bar in these sleek kitten heel mules designed with a mini criss-cross buckle strap and closed pointed toe. Complete the look with a coat.

    Fit & Features

    • Stiletto kitten heel
    • Closed pointed-toe
    • Mini criss-cross straps with buckle
    • Slingback strap
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-5087

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Modern Tortoiseshell Blue Light Eyeglasses

    Fit & Features

    • Oversized square-shaped frame
    • Hard plastic
    • Tortoiseshell pattern
    • Blue light block lenses
    • 100% UV protection 

     

    Style Number/Barcode: 07008-000056

    Category Name: Preppy Aesthetic Outfits

    Price: $9.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

    Product Badge:
    • Best Seller
  • Sleek Appeal Ribbed Knit Long Sleeve Bodysuit

    Every fashionista needs this long sleeve bodysuit to create dressed-up and down looks! Pair with a pleated skirt.

    Fit & Features

    • Ribbed knit fabrication, double-lined
    • Square neckline
    • Fitted long sleeves
    • Snap button closure
    • Thong bottom coverage
    • Runs true to size

    Style Number/Barcode: 06002-1994

    Category Name: Preppy Aesthetic Outfits

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L, XL

  • Wildly Cute Leopard Faux Suede Sneakers

    A pair of faux suede sneakers featuring a round toe, front lace-up closure, rubber gum sole, and a wildly cute leopard pattern. Perfect for styling with your everyday outfits.

    Fit & Features

    • Round toe
    • Leopard pattern
    • Faux suede material
    • Front lace-up closure
    • Rubber gum sole
    • Runs true to size

    Style Number/Barcode: 07407-0230

    Category Name: Preppy Aesthetic Outfits

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Polished Glam Belted Wide Leg Pants

    These high-rise knit pants will give your outfit a polished vibe. They feature a belted waist and a hip-hugging fit that flares out into the wide-leg hem. Pair with slingback heels.

    Fit & Features

    • Knit fabrication
    • High-rise waist, back zipper and hook-eye closure
    • Belted waist with metal grommets
    • Front vertical seams 
    • Straight-leg
    • Flared wide-leg hem
    • Runs true to size

    Style Number/Barcode: 06502-2546

    Category Name: Preppy Aesthetic Outfits

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Staple Crew Neck Cropped Knit Cardigan

    Bring your look together with a cropped knit cardigan that features a crew neckline, a button-down front, and fitted long sleeves. Pair with a pleated skirt and sneakers for a casual vibe! 

    Fit & Features

    • Knit fabric with ribbed hems, plenty of stretch
    • Crew neckline
    • Button-down front 
    • Long sleeves
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2066

    Category Name: Preppy Aesthetic Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

  • Preppy Chic Drop Waist Pleated Corduroy Mini Skirt

    Preppy and chic, this corduroy pleated mini skirt is such a trend! Pair with a crop sweater top and sneakers.

    Fit & Features

    • Corduroy fabrication, miminal stretch 
    • Drop waist design
    • Back zipper with hook-eye closure
    • Pleated
    • Mini-length hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 06301-0199

    Category Name: Preppy Aesthetic Outfits

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classically Chic Blue Light Eyeglasses

    Protect your eyes while looking chic in these blue light eyeglasses with an oversized square frame and UV protection perfect for indoor or outdoor use. Pair with a shoulder bag.

    Fit & Features

    • Oversized square-shaped frame
    • Hard plastic 
    • Blue light-blocking lenses
    • 100% UV protection 

    Style Number/Barcode: 07008-1118

    Category Name: Preppy Aesthetic Outfits

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Over the Knee Socks

    Style these basic over-the-knee socks with your favorite pleated skorts or denim rompers to give them a trendy finish.

    Fit & Features

    • Sheer knit fabrication
    • Over-the-knee fit

     

    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: 07306-0349

    Category Name: Preppy Aesthetic Outfits

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Tasteful Scrunch Mini Shoulder Bag

    A faux leather mini shoulder bag featuring a scrunched top handle, magnetic closure, and a spacious interior with a pocket perfect for stashing your keys, cards, phone, and more.

    Fit & Featuring

    • Scrunch top handle
    • Mini silhouette
    • Magnetic closure
    • Spacious interior with pocket
    • Faux leather material

    Style Number/Barcode: 07203-2043

    Category Name: Preppy Aesthetic Outfits

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Autumn Chic Faux Wool Long Belted Vest

    Feel the brisk chill in the air looking so chic in this faux wool long belted vest with a tie-front and dual side pockets to keep your hands warm. Pair with boots.

    Fit & Features

    • Faux wool fabrication, minimal stretch
    • 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: 06201-0545

    Category Name: Preppy Aesthetic Outfits

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free