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.

  • Buckle Up Babe Belted Wrap Skort

    Buckle up, babe—your outfit just leveled up. With a belted detail, a curve-hugging fit, and hidden shorts, this mini wrap skort is giving cool-girl confidence.

    Fit & Features

    • Knit fabric, moderate stretch
    • Mid-rise waist
    • Belted side detail
    • Faux wrap-front design
    • Mini-length hem
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000093

    Category Name: Preppy Rebel

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serving Sweetness Pleated Mini Skort

    Serving tennis-core with a side of spice. This pleated mini skort brings the cute with a flirty bow detail and keeps it comfy so you can serve looks all day, no sidelines needed.

    Fit & Features

    • Woven fabric, stretchy knit shorts lining
    • High-rise waist, hidden side zipper and hook-eye closure
    • Pleated mini-length skirt overlay with bow accents
    • Runs true to size

    Style Number/Barcode: 06403-000043

    Category Name: Preppy Rebel

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: L

    Product Badge:
    • Sale
  • Cool Girl Oversized Denim Jacket

    Effortlessly cool in an oversized fit, this denim jacket offers laidback vibes perfect for any day or night plans.

    Fit & Features

    • Light wash cotton-blend denim fabric
    • Long sleeves, button cuffs
    • Collar neckline
    • Hidden front snap-button closures
    • Front flap pockets with snap-button closures
    • Oversized fit

    Style Number/Barcode: 06203-000013

    Category Name: Preppy Rebel

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vintage Edge Corduroy Collar Denim Jacket

    A cool-girl classic with a vintage allure—this denim jacket levels up with a corduroy collar and cropped hem, perfect for creating spicy fall looks.

    Fit & Features

    • Denim fabric
    • Long sleeves, button cuffs
    • Curduroy collared neckline
    • Front pockets
    • Front zip-up closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06203-000015

    Category Name: Preppy Rebel

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Plans Halter Collared Corset Top

    Crisp days call for sleek layers. This halter collared corset top blends tailored structure with an open-back twist—perfect under blazers for the office or solo for a chic fall night out.

    Fit & Features

    • Poplin cotton-blend fabric
    • Halter collared neckline
    • Button-up front
    • Open cutout back with smocked side panels
    • Flexible boning inserts
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000123

    Category Name: Preppy Rebel

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest View Bow Pocket Denim Mini Skirt

    This denim mini skirt adds the cutest surprise with embroidered bow pockets that give soft girl allure. Pair it with a cute top and let the compliments roll in.

    Fit & Features

    • Light wash cotton denim fabric, no stretch
    • Mid-rise waist
    • Embroidered back bows
    • Form-hugging fit
    • Mini-length hem
    • Front button and hidden zipper closure
    • Three-pocket front design, belt loops
    • Runs true to size

    Style Number/Barcode: 06601-000012

    Category Name: Preppy Rebel

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hotter Than A Rodeo Strapless Romper

    The yeehaw energy is subtle but dangerous. With a flirty flared hem and a bold buckle-front, this romper is your new out-out fave.

    Fit & Features

    • Smooth ponte knit fabric, moderate stretch
    • Strapless neckline, belted accent, belt loops
    • Form-hugging bodice
    • Flared mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000098

    Category Name: Preppy Rebel

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Varsity Vibes Sweater Topper

    Serving varsity energy with a side of cozy-cutie. This sweater knit topper will keep your outfit looking trendy with your favorite bralette and denim jeans.

    Fit & Features

    • Sweater knit fabric
    • Long sleeves with stripes
    • V-neckline
    • Eight-stitched design
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000095

    Category Name: Preppy Rebel

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Layer Check Mock Neck Zip-Up Sweater

    Cozy, but make it cool. This mock neck zip-up sweater gives effortless flair, perfect for layering or styling on off-duty days.

    Fit & Features

    • Soft, stretchy knit fabric
    • Fitted long sleeves, rib knit cuffs
    • Rib knit mock neckline
    • Front zip-up closure
    • Fitted silhouette
    • Rib knit hem
    • Runs true to size

    Style Number/Barcode: 06005-000089

    Category Name: Preppy Rebel

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Ruffle Up And Go Tube Romper

    Short, sweet, and kinda irresistible. This tube romper flirts with every step thanks to its strapless straight neckline, drop waist design, and adorable ruffled overlay.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Strapless straight-across neckline
    • Drop waist design
    • Tiered ruffled mini-length overlay, A-line silhouette
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000099

    Category Name: Preppy Rebel

    Price: $14.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Charm Tie Front Sweater

    This isn’t just a sweater—it’s a whole vibe. With its soft rib knit, playful tie-front details, and cropped fit, it’s the perfect mix of cozy and flirty. Pair it with denim or layer over a slip dress for that effortlessly chic fall moment.

    Fit & Features

    • Soft rib knit stretch fabric
    • Long sleeves with flare cuffs
    • Crew neck
    • Tie front closures
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000099

    Category Name: Preppy Rebel

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Factor Faux Leather Bomber Jacket

    Instantly upgrade your street style with this faux leather bomber that’s cropped, collared, and cinched in all the right places. It’s that throw-on-and-look-hot kind of layer your closet’s been waiting for.

    Fit & Features

    • Vintage-inspired faux leather fabric, sewn-in woven lining
    • Long sleeves
    • Collared neckline
    • Front zip-up closure
    • Front pockets
    • Elasticized cinch crop hem
    • Runs true to size

    Style Number/Barcode: 06204-000032

    Category Name: Preppy Rebel

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XL

  • Too Cool To Pleat Mini Skort

    Serving attitude with every pleat—this skort is your new off-duty fave. The drop waist and zipper accents give it that edgy-meets-effortless vibe that pairs perfectly with everything from graphic tops to corsets.

    Fit & Features

    • Denim fabric
    • High-rise waist
    • Zipper front accents, back zipper closure
    • Pleated mini-length skirt overlay
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06603-000093

    Category Name: Preppy Rebel

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Rebel Edge Belted Denim Shorts

    Not your average shorts—this pair brings the attitude with a wide grommet belt and sleek denim finish. Style them with an oversized tee or crop top for that cool-girl, off-duty vibe.

    Fit & Features

    • Denim fabric
    • Studded waist belt
    • Mid-rise waist
    • Classic short length
    • Runs true to size

    Style Number/Barcode: 06603-000091

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Just Add Plans Strapless Skater Dress

    Effortlessly cute, always ready for fun. This strapless skater dress pairs a sleek fit with a pleated mini hem that’s made for twirling into your next big moment.

    Fit & Features

    • Smooth ponte fabric, knit lining
    • Strapless neckline
    • Skater silhouette
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000413

    Category Name: Preppy Rebel

    Price: $49.90

    Availability: In Stock

    Available Color: WINE

    Available Size: S, M, L

  • Cozy Check Plaid Knit Scarf

    Wrapped, but make it chic. This plaid knit scarf adds a soft, brushed texture that brings instant warmth and laid-back luxury—effortlessly tying together any cold-weather outfit with cozy polish.

    Fit & Features

    • Brushed knit fabric
    • Plaid pattern
    • Long fringe ends

    Style Number/Barcode: 07305-000026

    Category Name: Preppy Rebel

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denim Dream Strapless Belted Skater Dress

    She’s giving flirty, fun, and just the right amount of edge. The strapless fit and belted waist make this denim skater dress the definition of standout style.

    Fit & Features

    • Denim fabric
    • Strapless fold-over neckline
    • Smocked back
    • Belted drop waist
    • Short pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000232

    Category Name: Preppy Rebel

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hooked On Trouble Striped Top

    Business in the stripes, party in the cut—this hook-front striped top is a whole vibe. Pair it with your go-to mini skirt or jeans when you’re ready to blur the line between boss mode and nightlife.

    Fit & Features

    • Striped print, poplin woven fabric
    • Long sleeves
    • Collar neckline
    • Open front design with hardware hook closure
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06003-000164

    Category Name: Preppy Rebel

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAN

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Cool Intentions Long Sleeve Knit Bolero

    Layer it, slay it—this bolero is the ultimate fall cool-girl combo. Throw it on with your fave crop top or dress and you’re instantly serving street style.

    Fit & Features

    • Knit fabric
    • Long sleeves
    • Open front design
    • Ultra-cropped length hem
    • Runs true to size

    Style Number/Barcode: 06005-000123

    Category Name: Preppy Rebel

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • Checkmate Plaid Mini Skort

    Preppy with a playful twist. This plaid mini skort features front button details and a fitted waist, giving you that polished-yet-flirty vibe—perfect for pairing with the matching trench vest.

    Shop Matching Vest: Checkmate Plaid Trench Vest

    Fit & Features

    • Plaid pattern, faux wool-lined fabric
    • High-rise waist, button closures
    • Front flap pockets
    • Bodycon fit
    • Mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000056

    Category Name: Preppy Rebel

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Season’s Sleek Thigh-High Stiletto Boots

    The definition of drama. These scrunch thigh-high boots strike the perfect balance of luxe and daring, with a pointed toe and sleek stiletto heel made to elevate all your fall outfits.

    Fit & Features

    • 3” stiletto heel, 9.5” leg opening, 23” shaft
    • Pointed-toe
    • Side zipper closure
    • Thigh-high scrunch silhouette
    • Sleek faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000062

    Category Name: Preppy Rebel

    Price: $58.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9

  • Luxe Edit Faux Suede Blazer

    Tailored, timeless, and just the right amount of soft. This faux suede double-breasted blazer brings structure and sophistication with a plush twist—perfect for office dressing or upgrading your casual rotation.

    Fit & Features

    • Smooth faux suede fabric
    • Long sleeves
    • Lapel collar neckline
    • Double-breasted button closures
    • Front flap pockets
    • Longline hem
    • Runs true to size

    Style Number/Barcode: 06204-000044

    Category Name: Preppy Rebel

    Price: $54.90

    Availability: In Stock

    Available Color: BLACK, BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • All Tied Together Bungee Corset Top

    A daring twist on classic corsetry—this strapless corset top features all-over lace-up bungee detail for a bold, body-sculpting fit.

    Fit & Features

    • Woven fabric, sewn-in knit lining, slight stretch
    • Strapless neckline
    • All over bungee lace-up designs
    • Flexible boning inserts
    • Back zipper and hook-eye closure
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000167

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Polished Moves Faux Leather Skort

    This faux leather skort brings a sleek edge with its clean silhouette and subtle side slits. Pair it with a sweater or oversized blazer for a look that’s equal parts flirty and polished.

    Fit & Features

    • Coated faux leather fabric
    • High-rise waist
    • Form-hugging fit
    • Front slit
    • Mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000059

    Category Name: Preppy Rebel

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L