Preppy Rebel

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tag of the document. This will help to improve the load of the images // during color swatches interaction on PLP const preloadBackground = (entries, observer) => { entries.forEach(async (entry) => { if (entry.isIntersecting) { const swatch = entry.target; const images = swatch.dataset.varimg.split(','); images.forEach((img, index) => { // preload image const link = document.createElement('link'); link.href = buildSrc(img); link.imagesrcset = getSrcset(img); link.imagesizes = cssImageMediaCondition; link.rel = 'preload'; link.as = 'image'; document.getElementsByTagName('head')[0].appendChild(link); }); swatch.removeAttribute('data-varimg'); switchObserver.unobserve(swatch); } }); }; const switchObserver = new IntersectionObserver(preloadBackground, { root: null, // Default is the viewport rootMargin: '30px', threshold: 0.05, // Load image when 10% of the div is visible }); // Sort options function getPageParam() { const urlParams = new URLSearchParams(window.location.search); const pageParam = urlParams.get('page'); return pageParam ? parseInt(pageParam, 10) : 1; } domLoadedPage = getPageParam(); setupSortDropdown('.fs_sort_by_wrap_desktop', '.fs_sort_by_options_desktop', '.fs_sort_by_select_desktop'); const sortBySelect = document.getElementById('sortByDesktop'); let sortByValue = getSortBy(); // call the function and store the returned value sortBySelect.value = sortByValue; // update the desktop dropdown value on page load // update sort mobile dropdown value on page load const validSortOptions = ['price_min_to_max', 'price_max_to_min', 'creation_date', 'relevency']; sortByValue = validSortOptions.includes(sortByValue) ? sortByValue : 'relevency'; const inputField = document.querySelector(`form [data-value="${sortByValue}"]`); if (inputField) { inputField.checked = true; // update the value of the option } else { console.error(`No radio button found with data-value="${sortByValue}"`); } const form = document.getElementById('sortForm'); if (form) { form.addEventListener('change', (event) => { if (event.target.name === 'sort') { const selectedValue = event.target.getAttribute('data-value'); if (selectedValue && validSortOptions.includes(selectedValue)) { setUrlParam('sortBy', selectedValue, true); resetPageAndScroll(); updateOtherDropdown(selectedValue); } } }); } updateOtherDropdown(getSortBy()); if (sortBySelect) { sortBySelect.addEventListener('change', function () { if (sortBySelect.value && validSortOptions.includes(sortBySelect.value)) { setUrlParam('sortBy', sortBySelect.value, true); } }); } // Description 'read more' function toggleReadMore(button) { const container = button.parentNode; const isExpanded = container.getAttribute('aria-expanded') === 'true'; container.setAttribute('aria-expanded', !isExpanded); if (isExpanded) { button.querySelector('.button-text').textContent = 'more'; } else { button.querySelector('.button-text').textContent = 'Show less'; } } function visibleReadMore() { const toggleButtons = document.querySelectorAll('.fs_collection_top_toggle'); toggleButtons.forEach(button => { const description_children = button.previousElementSibling.children; let description_scroll_width = 0; let description_client_width = 0; for(const child of description_children) { description_scroll_width += child.scrollWidth; description_client_width += child.clientWidth; }; button.style.display = (description_scroll_width > description_client_width) ? 'block' : 'none'; }); } window.addEventListener('DOMContentLoaded', visibleReadMore); // category pills GTM const categories = document.querySelectorAll('.category-pills__pill'); let category; let categoryHandle; let categoryId; const pushCategoryPills = (category, categoryHandle, categoryId, typeCategory) => { if (category && categoryHandle && categoryId && typeCategory) { const categoryPills = { event: `categoryPills`, category: category, categoryHandle: categoryHandle, categoryId: categoryId, typeCategory: typeCategory }; window.dataLayer.push(categoryPills); } } categories?.forEach(category => { category.addEventListener('click', function(e) { try { category = e.currentTarget.getAttribute('data-category'); categoryHandle = e.currentTarget.getAttribute('data-collection-handle'); categoryId = e.currentTarget.getAttribute('data-collection-id'); typeCategory = e.currentTarget.getAttribute('data-type-category'); pushCategoryPills(category, categoryHandle, categoryId, typeCategory); } catch (error) { console.error('Error in category click event:', error); } }) })

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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.

  • 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 Rebel

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Rebel

    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 Rebel

    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 Rebel

    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 Rebel

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Rebel

    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 Rebel

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Rebel

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Rebel

    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 with extender

    Style Number/Barcode: 07003-0635

    Category Name: Preppy Rebel

    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 Rebel

    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 Rebel

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smooth Moves PU High-Rise Shorts

    Oh-so-contemporary and sleek, these smooth faux leather shorts feature a high-rise waist, front snap-button, hidden zipper closure, side pockets, seam detailing, and a fitted cheeky hem. The lined faux leather fabric has minimal stretch. Complete the look in a basic tee and boots for an edgy vibe.

    Fit & Features

    • High-rise waist
    • Front snap-button and hidden zipper closure
    • Side pockets
    • Seam detailing
    • Fitted, cheeky hem
    • Faux leather lined fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0241

    Category Name: Preppy Rebel

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L, XS

  • Cool-Girl Vibes Faux Leather Wrap Skort

    Give off those cool-girl vibes in this sleek faux leather wrap skort! It features a high-rise waist, a wrap-front overlay with pleated detailing, and fitted shorts. The smooth faux leather fabric offers a moderate stretch. Style this skort with a chic corset top and ankle booties.

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Wrap-front overlay, pleating
    • Fitted shorts
    • Smooth faux leather fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06403-0244

    Category Name: Preppy Rebel

    Price: $22.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Trendsetting Girlie Long Sleeve Denim Shrug Jacket

    You'll always make a trendsetting impression in this denim shrug jacket! Perfect for layering over every cute 'fit, this jacket features relaxed long sleeves with button closures, a collar neckline and open front design, and an ultra-cropped hem that flaunts your figure. Complete the look in cute sandals.

    Fit & Features

    • Light wash denim fabric, no stretch
    • Collar neckline
    • Ultra cropped hem
    • Runs true to size

    Style Number/Barcode: 06203-0524

    Category Name: Preppy Rebel

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Turn Up Cargo Metallic Faux Leather Shorts

    Turn up the shine in these groovy metallic faux leather shorts perfect for themed parties! With a high-rise waist and form-hugging fit, these shorts accentuate your curves while providing a flattering silhouette. The cargo flap pockets offer functionality while the front button and hidden zipper closure secure the style. Complete the look in a mesh long sleeve top and heels!

    Fit & Features

    • Coated metallic faux leather fabric, slight stretch
    • High-rise waist
    • Form-hugging fit
    • Front button and hidden zipper closure
    • Three waist pockets, lower cargo flap pockets
    • Runs true to size

    Style Number/Barcode: 06403-0381

    Category Name: Preppy Rebel

    Price: $26.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling Cool Pleated Faux Leather Mini Skort

    Feel cool and cute in this faux leather mini skort out at a concert or party! The high-rise waist and pleated silhouette create a flattering fit while the mini-length hem adds a touch of sass. Plus, the stretchy knit shorts lining ensures comfort all day long. Complete the look in a crop tee.

    Fit & Features

    • Faux leather fabric, stretchy knit shorts lining
    • High-rise waist
    • Back zipper closure
    • Pleated silhouette
    • Mini-length hem
    • Skort in size small has a 10.5" front rise with a 1.5" inseam
    • Runs true to size

    Style Number/Barcode: 06503-1159

    Category Name: Preppy Rebel

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Play On In Plaid Blanket Scarf

    Fit & Features

    • Soft knit fabrication
    • Oversized blanket design
    • Plaid print
    • Fringe detailing

    Style Number/Barcode: 07305-0509

    Category Name: Preppy Rebel

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Classic Cropped Denim Jacket

    This trendy classic cropped denim jacket features a collared neckline with a button-down front, long sleeves with a single button detail you can cuff, buttoned chest pockets, and a fitted silhouette. Layer over a basic crop top for everyday styling.

    Fit & Features

    • Cotton-blend denim fabric, moderate stretch
    • Collared neckline
    • Button-down front
    • Long sleeves with single-button detail
    • Buttoned chest pockets
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06203-0560

    Category Name: Preppy Rebel

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Charm Cropped Knit Cardigan

    Cozy and charming, this knit cardigan offers a classic design with a button-down front for versatile styling options and a cropped hem. 

    Fit & Features

    • Knit fabrication, moderate stretch 
    • Button-down front 
    • Long sleeves
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2153

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: BURGUNDY, TAUPE, BLACK

    Available Size: S, M, L, XS

  • Plaid Charm Pleated Drop Waist Skort

    Have fun in the plaid charm pleated drop waist skort! With a playful plaid pattern, hidden shorts, and dual tab accents, this skort is your go-to for a cheeky, carefree vibe.

    Fit & Features

    • Woven knit fabrication
    • Drop waist 
    • Dual tab accent at waist
    • Pleated
    • Plaid pattern
    • Mini skirt overlay
    • Hidden shorts
    • Runs true to size

    Style Number/Barcode: 06403-1059

    Category Name: Preppy Rebel

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Contrast Tube Mini Dress

    Sophisticated yet flirty, this strapless mini dress turns heads with its fitted bodice and pleated skirt. Add heels and jewelry for lunch in the city or a chic wine bar with the girls!

    Fit & Features

    • Woven fabric, contrast design
    • Tube strapless neckline
    • Fitted bodice
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5913

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Chic Structure Long Sleeve Cropped Corset Top

    Fit & Features

    • Woven fabric with minimal stretch
    • Collared V-neckline
    • Button-down front closure
    • Long sleeves with dual button details
    • Corset-like bodice with flexible boning, side smocked accents
    • Angled cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2660

    Category Name: Preppy Rebel

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Looking Cool Belted And Pleated Mini Skort

    Elevate your style with this pleated mini skort. Featuring a high-rise waist, double belt, and pleated overlay, this skort is your go-to for effortless chic vibes.

    Fit & Features

    • Twill woven fabric
    • High-rise waist, double belted front design
    • Mini-length pleated overlay
    • Side zipper closure
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06303-0290

    Category Name: Preppy Rebel

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free