Preppy Rebel
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 Rebel
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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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Effortless Tease Long Sleeve Crop Top
A little twist, a lot of charm—this rib knit crop top brings that subtly flirty vibe you can throw on with anything. The long sleeves balance the twisted bust detail, serving a look that feels pulled together without trying too hard.
Fit & Features
- Rib knit seamless stretchy fabric
- Twisted bust detail
- Fitted long sleeves
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06002-000469
Category Name: Preppy Rebel
Price: $32.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
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Statement Season Faux Leather Trench Coat
Statement season starts here. This sleek faux leather trench coat brings a chic attitude with a perfectly structured fit—made for nights out, city strolls, and every unapologetically confident moment in between. Style with the matching mini skort.
Shop Matching Bottoms: Statement Season Faux Leather Mini Skort
Fit & Features
- Patent faux leather fabric, crinkle texture
- Lapel collar, back flap accent
- Long sleeves, strap details
- Open front, tie-front belt
- Long-length hem
- Structured fit
- Runs true to size
Style Number/Barcode: 06204-000073
Category Name: Preppy Rebel
Price: $79.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
Product Badge:- Ships Free
- Patent faux leather fabric, crinkle texture
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Tailored Mood Plaid Woven Blazer
Your “I planned this” blazer—clean, tailored, and instantly elevated. The plaid woven finish gives it that strategic, cool-girl polish that works from brunch to late-night plans without ever trying too hard.
Shop Matching Shorts: Tailored Mood Plaid Woven Shorts
Fit & Features
- Plaid printed woven fabric
- Structured tailored silhouette
- Notched lapel neckline
- Front flap pockets and multi-button closure
- Runs true to size
Style Number/Barcode: 06204-000059
Category Name: Preppy Rebel
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free