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.
HomePreppy Aesthetic Outfits
Preppy Aesthetic Outfits
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.
-
Keep It Casual Pleated Mini Skort
Meet your new fave: the keep it casual pleated mini skort. With a high-rise waist, hidden zipper, and chic pleats, it's perfect for any adventure. Rock it with confidence, girl!
Shop Matching Top: Keep It Casual Square Neck Cropped Tank Top
Fit & Features
- Woven fabric
- High-rise waist, belt loops
- Hidden side zipper and hook-eye closure
- Contrast peeking trim
- Front mini-length pleated overlay, A-line silhouette
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-1082
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: CHARCOAL
Available Size: L
Product Badge:- Part of a Set
-
Sporty Chic Contrast Sneakers
Fit & Features
- Round toe
- Faux leather with faux suede contrast
- Lace-up front closure
- Rubber gum sole
- Silver features metallic contrast
- Runs true to size
Style Number/Barcode: 07407-0237
Category Name: Preppy Aesthetic Outfits
Price: $28.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Sleek Detail Three-Pack Hoop Earrings Set
Flaunt your style with the sleek detail three-pack hoop earrings set. Featuring triangle, oval, and angled hoops, these chic pieces are perfect for any occasion.
Fit & Features
- Three-pack earrings set
- Triangle-shaped hoops
- Oval-shaped hoops
- Angled hoops
- Omega and post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-2349
Category Name: Preppy Aesthetic Outfits
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cozy Glam Cable Knit Long Sleeve Bolero
Level up your look with this cable knit long sleeve bolero. Featuring a heart-shaped stitch and cropped hem, this open-front design is your new fave for chic vibes.
Fit & Features
- Cable knit soft fabrication
- Open-front design
- Long sleeves with a heart-shaped stitch pattern
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-2128
Category Name: Preppy Aesthetic Outfits
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
On The Move Faux Suede Long Blazer
Fit & Features
- Faux suede fabric with minimal stretch
- Lapel collar
- Long sleeves
- Side pockets
- Long hem length, back slit detail
- Runs true to size
Style Number/Barcode: 06204-1952
Category Name: Preppy Aesthetic Outfits
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Icon Era Houndstooth Woven Blazer
Shop Matching Bottoms: Icon Era Houndstooth Woven Mini Skirt
Fit & Features
- Houndstooth woven fabric, sewn-in woven lining
- Lapel collar
- Long sleeves
- Double-breasted button closure
- Front flap pockets
- Runs true to size
Style Number/Barcode: 06204-1955
Category Name: Preppy Aesthetic Outfits
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Casual Look Denim Mini Skort
Hop into this denim mini skort in brown and flaunt your style! With a high-rise waist and cheeky front slits, this skort is your go-to for a fab, form-hugging fit.
Fit & Features
- Denim fabric
- High-rise waist
- Back zipper closure
- Dual short front slits
- Mini-length overlay, fitted shorts
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0427
Category Name: Preppy Aesthetic Outfits
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, XL
-
Edgy Prep Plaid Pleated Mini Skort
Fit & Features
- Plaid faux wool fabric
- Mid-rise fit, belted front
- Drop waist design
- Mini-length pleated overlay
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-1115
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Perfect In Plaid Drop Waist A-Line Romper
Be the trendsetter in this plaid drop waist a-line romper. With a square neckline, cute bow, and pleated overlay, this romper is your go-to for effortless style.
Fit & Features
- Plaid printed knit fabric
- Square neckline with mini bow detail
- Tank shoulder straps, square back
- Drop waist design
- Mini-length pleated overlay, A-line silhouette
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06503-1261
Category Name: Preppy Aesthetic Outfits
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
So Glam Chain Link Charm Bracelet
Fit & Features
- Chain-link
- Watch charm
- Heart charm
- Butterfly charm
- Ribbon charm
- Flower charm
- Lobster clasp closure
Style Number/Barcode: 07003-0635
Category Name: Preppy Aesthetic Outfits
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Desire For Chic Faux Leather Mini Bag
Fit & Features
- Faux leather material
- O-ring handle
- Detachable chain shoulder strap
- Zipper closure
- Mini design
- Spacious interior
Style Number/Barcode: 07203-2082
Category Name: Preppy Aesthetic Outfits
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Icon Era Houndstooth Woven Mini Skirt
Shop Matching Jacket: Icon Era Houndstooth Woven Blazer
Fit & Features
- Houndstooth woven fabric, stretchy knit shorts
- High-rise waist
- Back zipper hook-eye closure
- Short side slit
- Mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06401-0728
Category Name: Preppy Aesthetic Outfits
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free