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.

  • Fierce And Trendy Mid-Rise Leopard Mini Skort

    Unleash your fierce and trendy side in this leopard mini skort! The belted waist and pleated skirt overlay create a trendy look while the mini hem shows off your legs.

    Fit & Features

    • Leopard print, denim fabric
    • Mid-rise belted waist, belt loop accents
    • Pleated skirt overlay, side zipper closure
    • Shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06603-0430

    Category Name: Preppy Rebel

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: M, L

    Product Badge:
    • Sale
  • Preppy Edit Pinstripe Mini Dress

    The perfect dress for fall—this strapless pinstripe mini dress blends polished structure with playful pleats. Toss on a blazer or knee-high boots for seasonal chic.

    Fit & Features

    • Pinstripe pattern, woven fabric
    • Strapless collared neckline
    • Button front
    • Fitted bodice
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5993

    Category Name: Preppy Rebel

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GRAY

    Available Size: M, L

    Product Badge:
    • Sale
  • Absolute Darling Gingham Pleated Skort

    Look and feel so darling in this gingham pleated skort for warm weather dressing!

    Fit & Features

    • Gingham print, woven fabric, stretchy knit shorts lining
    • High-rise waist, side zipper closure
    • A-line silhouette
    • Pleated mini-length skirt overlay
    • Runs true to size

    Style Number/Barcode: 06403-1097

    Category Name: Preppy Rebel

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Edge Low-Rise Hot Shorts

    Take your style to the edge in these faux leather hot shorts at concerts, festivals, and nights out!

    Fit & Features

    • Faux leather woven fabric
    • Low-rise waist, belt loop accents
    • Hidden front hook-eye and zipper closures
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06403-1106

    Category Name: Preppy Rebel

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping It Cute Pleated Ponte Skort

    Keeping it cute has never looked so flirty in this ponte skort boasting a flattering high-rise waist and pleated skirt overlay with shorts lining to give coverage. Style the skort with a long sleeve top.

    Fit & Features

    • Smooth ponte knit fabric
    • High-rise waist
    • Pleated skirt overlay
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-1263

    Category Name: Preppy Rebel

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Around The City Mid-Rise Pleated Skort

    A perfect faux leather pleated skort for adventuring around the city!

    Fit & Features

    • Vintage-inspired faux leather fabric, stretchy knit shorts lining
    • Mid-rise waist
    • Side zipper closure
    • Belt loop accents
    • Pleated mini skirt overlay
    • Runs true to size

    Style Number/Barcode: 06403-1112

    Category Name: Preppy Rebel

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Flirty Flair Halter Pleated Romper

    Catch every eye in this halter pleated romper for an adorable look for brunch or a day date!

    Fit & Features

    • Ponte fabric
    • Halter neckline with tie closure
    • Form-hugging bodice
    • Pleated mini-length hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000012

    Category Name: Preppy Rebel

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Baby Got Back Basic Crew Neck Crop Tee

    Getting dressed is a stylish breeze when you have this basic crew neck tee with a flirty open back design to elevate your favorite bottoms!

    Fit & Features

    • Smooth stretchy knit fabric
    • Crew neck
    • Short sleeves
    • Open back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000039

    Category Name: Preppy Rebel

    Price: $19.90

    Availability: In Stock

    Available Color: WHITE, PURPLE

    Available Size: L, S

  • Adorably Chic Pleated Linen Mini Skort

    Adorably chic, this lightweight linen skort features a mid-rise waist, a pleated mini-length overlay with an A-line silhouette, and hidden shorts. Style with the matching halter top for a cutesy vibe.

    Shop Matching Top: Adorably Chic Bow-Trim Linen Halter Top

    Fit & Features

    • Linen-blend woven fabric
    • Mid-rise waist
    • Pleating
    • Mini-length overlay, A-line silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06303-000023

    Category Name: Preppy Rebel

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: L

    Product Badge:
    • Sale
  • Adorably Chic Bow-Trim Linen Halter Top

    Adorably chic, this lightweight linen top features a halter square neckline, a dainty bow trim design leading to a front slit, and a fitted mid-length hem. Style with the matching mini skort for a cutesy vibe.

    Shop Matching Bottoms: Adorably Chic Pleated Linen Mini Skort

    Fit & Features

    • Linen-blend woven fabric
    • Sleeveless square neckline
    • Halter strap, partially open back
    • Bow trim front design, slit detail
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06003-000038

    Category Name: Preppy Rebel

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Get It Girl Belted Skater Dress

    Get a bold style in this belted skater dress! The fitted waist belt and seam details accentuate your silhouette, while the pleated skirt adds movement.

    Fit & Features

    • Twill stretch fabric, stretchy knit lining
    • Strapless neckline with grommet trim
    • Back zipper and hook-eye closure
    • Seam detailing
    • Belted waist
    • Skater silhouette, pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000105

    Category Name: Preppy Rebel

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

  • Made To Standout Faux Leather A-Line Skort

    Dress to stand out in this cute faux leather skort in a flowy A-line silhouette perfect for a night out dinner and drinks!

    Fit & Features

    • Faux leather fabric
    • High-rise waist
    • A-line silhouette
    • Short-length skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000034

    Category Name: Preppy Rebel

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic And Coveted Trucker Denim Jacket

    A classic trucker denim jacket you'll covet! This jacket offers relaxed long sleeves, a cropped hem, and classic jean jacket construction. It's perfect for day or night styling.

    Fit & Features

    • Denim cotton fabric
    • Collar neckline
    • Relaxed long sleeves, button cuffs
    • Front flap pockets
    • Front button-up closures
    • Cropped length hem
    • Runs true to size

    Style Number/Barcode: 06203-000007

    Category Name: Preppy Rebel

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Flair Faux Leather Skater Romper

    Show off a sleek flair in this smooth faux leather skater romper with a drop waist and adorable fit-and-flare silhouette. Pair with strappy heels for a night out.

    Fit & Features

    • Smooth faux leather fabric, moderate stretch
    • Sleeveless square neck and back
    • Tank shoulder straps
    • Drop waist, small bow detail
    • Pleated short skater skirt overlay, fitted shorts
    • Romper in size small is 29" shoulder to hem with a 9" front rise and a 1.5" inseam
    • Runs true to size

    Style Number/Barcode: 06503-000038

    Category Name: Preppy Rebel

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She’s The Moment Tie-Front Halter Top

    Serving main character energy with every knot—this top is that girl. The halter V-neck and flirty tie-fronts give it an effortlessly hot vibe that’s perf for your next weekend adventure.

    Fit & Features

    • Twill woven fabric
    • Sleeveless halter V-neckline
    • Multi-tie-front design
    • Partially open back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000068

    Category Name: Preppy Rebel

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

    Product Badge:
    • Sale
  • Girly Chic Lace Trim Mini Skort

    Serve all the girly chic vibes in this cute mini skort designed with a drop waist, pleating, and a peeking lace trim.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Drop waist design
    • Pleating
    • Mini-length overlay, skater silhouette, sheer lace trim
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000052

    Category Name: Preppy Rebel

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

    Product Badge:
    • Sale
  • Sweet and Sleek Halter Crop Top

    Flirty fit, effortless feel. This halter crop top hugs in all the right places with a square neckline that’s cute for brunch and weekend fun.

    Fit & Features

    • Woven fabric, slight stretch
    • Square halter neckline, elasticized strap
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000094

    Category Name: Preppy Rebel

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Prep School Crush Plaid Mini Skort

    Plaid but make it flirty—this pleated mini skort has side bow ties and a preppy vibe that’s giving major cool-girl energy. Perfect with tees and chunky knits or crop tops and heels for a cute evening look.

    Fit & Features

    • Mid-rise waist
    • Side bow accents
    • Pleated mini skirt overlay
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000035

    Category Name: Preppy Rebel

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serve Looks Not Limits Faux Leather Belted Skort

    Ready to turn sidewalks into runways? This faux leather belted mini skort brings all the sass with none of the stress. The high-rise waist snatches you in, while the front slit serves just the right amount of drama.

    Fit & Features

    • Faux leather fabric
    • High-rise waist with belted accent
    • Side zipper and hook-eye closure
    • Form-hugging silhouette
    • Front high slit, mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000038

    Category Name: Preppy Rebel

    Price: $11.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty On Arrival Faux Leather Ruffle Skort

    Catch her in the wild, causing a scene in this tiered faux leather skort. Built-in shorts keep it chill while the ruffles keep it spicy.

    Fit & Features

    • Faux leather fabric, stretchy knit shorts lining
    • High-rise waist
    • Side zipper and hook-eye closure
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06403-000037

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: M

  • Buckle Up Baby Pleated Skort

    Serving schoolgirl but make it fashionable. With sharp pleats and a bold belt moment, this skort is your go-to for flirty fits with a little edge.

    Fit & Features

    • Denim fabric, stretchy knit shorts lining
    • High-rise belted waist, side zipper and hook-eye closure
    • Pleated mini-length skirt overlay
    • Runs true to size

    Style Number/Barcode: 06603-000059

    Category Name: Preppy Rebel

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BEIGE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Plaid Attitude Pleated Mini Skort

    Prep, but make it playful. This plaid pleated mini skort features a buckle belt detail that gives school-girl energy with a cool-girl twist. Perfect for pairing with the matching cropped vest.

    Shop Matching Top: Plaid Attitude Cropped Vest Top

    Fit & Features

    • Plaid woven fabric
    • Mid-rise waist with belt detail
    • Pleated mini-length skirt overlay
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000040

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Prepped For Style Pleated Plaid Skort

    This plaid pleated mini skort is flirty, playful, and perfect for styling with baby tees or oversized layered this fall season!

    Fit & Features

    • Plaid print, woven fabric, shorts lining
    • Low-rise waist
    • Pleated mini-length skirt overlay
    • Runs true to size

    Style Number/Barcode: 06403-000041

    Category Name: Preppy Rebel

    Price: $11.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Lot Iconic Pleated Belt Mini Skort

    This pleated skort serves cool-girl energy with a sleek belted accent and an effortlessly bold look that elevates your everyday style.

    Fit & Features

    • Faux leather fabric, stretchy knit shorts lining
    • Mid-rise waist, side zipper closure
    • Belted waist accent
    • Pleated mini-length hem with slit accent
    • Runs true to size

    Style Number/Barcode: 06403-000042

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L