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 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.
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Boldly Chic Metal Ring Multipack
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: In Stock
Available Color: GOLD
Available Size: 7, 8
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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: $23.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: NAVY
Available Size: S, M, L
Product Badge:- Sale
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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: $24.90
Availability: Out of Stock
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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
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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
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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
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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
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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
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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
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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
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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
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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: In Stock
Available Color: GRAY
Available Size: XS
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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
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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: $48.90
Availability: Out of Stock