Preppy Aesthetic Outfits

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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.

  • Boldly Chic Metal Ring Multipack

    Level up your style with the boldly chic metal ring multipack. Featuring four chunky designs, these rings are perfect for any occasion, from meetings to happy hours.

    Fit & Features

    • Multipack includes four rings
    • Variety of chunky metal designs

    Style Number/Barcode: 07004-0432

    Category Name: Preppy Aesthetic Outfits

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Minimal Glam Geometric Ring Multipack

    Fit & Features

    • Multipack includes three rings
    • Variety of chunky geometric designs

    Style Number/Barcode: 07004-0431

    Category Name: Preppy Aesthetic Outfits

    Price: $10.90

    Availability: Out of Stock

  • Boldly Chic Metal Bracelet Multipack

    Fit & Features

    • Multipack includes three bracelets
    • Metal coil design
    • Stretch fit

    Style Number/Barcode: 07003-0681

    Category Name: Preppy Aesthetic Outfits

    Price: $12.90

    Availability: Out of Stock

  • Trend Alert Beaded Coin Bracelet

    Fit & Features

    • Double-row beaded design
    • Small coin charm
    • O-ring and toggle closure

    Style Number/Barcode: 07003-0628

    Category Name: Preppy Aesthetic Outfits

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

  • Dainty Details Three-Pack Bracelet Set

    Fit & Features

    • Multipack includes three bracelets
    • One mini chain-link bracelet
    • One rhinestone tennis bracelet
    • One beaded bracelet

    Style Number/Barcode: 07003-0642

    Category Name: Preppy Aesthetic Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gleaming Chic Beaded Bracelet

    Fit & Features

    • Multi-row design
    • Beaded

    Style Number/Barcode: 07003-0641

    Category Name: Preppy Aesthetic Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Mixed Metal Drop Earrings

    Fit & Features

    • Mixed metals
    • Geometric drop design
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-2231

    Category Name: Preppy Aesthetic Outfits

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

  • Time For Luxe Bangle Bracelet

    Fit & Features

    • Slide on design
    • Beaded accents
    • Sleek metal

    Style Number/Barcode: 07003-0640

    Category Name: Preppy Aesthetic Outfits

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleekest Style Coiled Metal Choker Necklace

    Fit & Features

    • Single row
    • Coiled metal design

    Style Number/Barcode: 07002-1986

    Category Name: Preppy Aesthetic Outfits

    Price: $3.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • First Look Contrast Wide-Leg Pants

    Fit & Features

    • Woven knit fabrication, moderate stretch 
    • High-rise waist
    • Contrast-hued foldover waist accent
    • Slant pockets
    • Wide-leg hem
    • Runs true to size

    Style Number/Barcode: 06402-1454

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crafted Luxe Clasp Bangle Bracelet

    Fit & Features

    • Open-clasp design
    • Sleek metal material

    Style Number/Barcode: 07003-0632

    Category Name: Preppy Aesthetic Outfits

    Price: $10.90

    Availability: Out of Stock

  • Varsity Chic Button-Down Sweater Jacket

    Fit & Features

    • Knit fabric with moderate stretch
    • "AC" embroidered script, striped ribbed hems
    • Flat collared neckline
    • Contrast long sleeves with tapered hems
    • Button-down front, dual front pockets
    • Tapered hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-2246

    Category Name: Preppy Aesthetic Outfits

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Muse Faux Leather Bow Handbag

    Fit & Features

    • Faux leather fabrication
    • Top zipper closure
    • Shoulder strap accented with bow
    • Scrunch detailing
    • Half-moon shaped body

    Style Number/Barcode: 07203-2062

    Category Name: Preppy Aesthetic Outfits

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

  • Polished Perfection Contrast Waist Pants

    Fit & Features

    • Woven knit fabrication
    • High-rise waist, hidden zipper closure
    • Contrast-hued waist trim accent
    • Belt loops with slant pockets
    • Straight leg
    • Pants in size small has a 13" front rise with a 29" inseam
    • Runs true to size

    Style Number/Barcode: 06402-1455

    Category Name: Preppy Aesthetic Outfits

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dainty Charm Six-Pack Earring Set

    Fit & Features

    • Includes six pairs of earrings
    • 1 rhinestone stud pair
    • 2 mini-hoop pairs
    • 1 mini door-knocker pair
    • 1 twist-knot pair
    • 1 clover-shaped pair

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-2164

    Category Name: Preppy Aesthetic Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

  • Chic Connections Chain Bracelet Multi-Pack

    Fit & Features

    • Includes five bracelets
    • Chain link designs
    • Snake chain designs
    • Beaded designs

    Style Number/Barcode: 07003-0633

    Category Name: Preppy Aesthetic Outfits

    Price: $12.90

    Availability: Out of Stock

  • Chic Allure Checkered Knit Sleeveless Vest

    Fit & Features

    • Knit fabrication
    • V-neckline
    • Sleeveless
    • Checkered pattern
    • Ribbed hem
    • Long-sleeve top pictured not included
    • Runs true to size

    Style Number/Barcode: 06005-2251

    Category Name: Preppy Aesthetic Outfits

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Strut Slingback Stiletto Pumps

    Fit & Features

    • Stiletto heel
    • Slingback ankle strap, chainlink metal accent
    • Closed pointed toe
    • Faux patent leather material
    • Runs true to size

    Style Number/Barcode: 07401-5082

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

  • Wild Glam Leopard Print Slingback Pumps

    Fit & Features

    • Stiletto heel
    • Closed-pointed toe
    • Slingback strap, accented with chainlink detail
    • Leopard print
    • Faux patent leather material 
    • Runs true to size

    Style Number/Barcode: 07401-5081

    Category Name: Preppy Aesthetic Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Plaid Perfection Faux Wool Mini Skort

    Layer on the chic style with this plaid mini skort designed with structured faux wool fabric. It features a high-rise waist, a mini-length overlay with a short side slit, and hidden fitted knit shorts for coverage. Style with the matching long coat!

    Shop Matching Coat: Plaid Perfection Faux Wool Long Coat

    Fit & Features

    • Plaid faux wool fabric, no stretch
    • High-rise waist
    • Back zipper with hook-eye closure
    • Mini-length overlay with side slit
    • Hidden fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06403-0617

    Category Name: Preppy Aesthetic Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Twist Three-Pack Earrings Set

    Fit & Features

    • Includes three pairs of earrings
    • 1 pair mini door-knocker design
    • 1 pair open-hoop design
    • 1 pair multi-interlocking hoop design
    • Post-back closures, rubber stoppers

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-2181

    Category Name: Preppy Aesthetic Outfits

    Price: $10.90

    Availability: Out of Stock

  • Classic Charm Plaid Wrap Skort

    Shop Matching Jacket: Classic Charm Plaid Trench Coat

    Fit & Features

    • Faux wool fabrication
    • Mid-rise waist, back zipper and hook-eye closure
    • Mini skirt wrap overlay
    • Hidden stretchy knit shorts
    • Plaid pattern
    • Runs true to size

    Style Number/Barcode: 06403-1065

    Category Name: Preppy Aesthetic Outfits

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Factor Ribbed Knit Off-The-Shoulder Sweater

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Off-the-shoulder neckline, fold-over design
    • Long sleeves
    • Oversized fit

    Style Number/Barcode: 06005-2152

    Category Name: Preppy Aesthetic Outfits

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Here To Slay Under-The-Knee Block Heel Boots

    Fit & Features

    • 3” block heel, 7.5” leg opening, 16” shaft height
    • Half faux leather, half spandex material
    • Under-the-knee height
    • Square toe
    • Complete inner zipper closure
    • Runs true to size

    Style Number/Barcode: 07402-1079

    Category Name: Preppy Aesthetic Outfits

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free