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.

  • Wild Chic Leopard Removable Faux Fur Cardigan

    Sweet, but with claws. This tie-front crop cardigan brings cozy meets chaos with its soft knit fabric and removable leopard faux fur trim. Whether you style it layered or solo, it’s the ultimate “don’t mess, I’m vibing” kind of top.

    Fit & Features

    • Soft rib knit stretchy fabric
    • Removable leopard faux fur collar
    • Tie-front closure
    • Fitted long sleeves with leopard removable faux fur cuffs
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000047

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Street Chic Poplin Corset Crop Top

    Button-up vibes, but make it bold—this poplin corset top brings structure with an off-the-shoulder collar and cropped fit. Perfect with wide-leg trousers or a mini skirt when you’re feeling polished but daring.

    Fit & Features

    • Cotton poplin woven fabric, no stretch
    • Collared off-the-shoulder neckline
    • Long sleeves with button cuffs
    • Corset-style bodice, flexible boning, hidden hook and eye fasteners
    • Back zipper and hook-eye closure, stretchy smocked panel
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000170

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Ace The Look Plaid Pleated Romper

    Plaid but make it playful—this strapless romper brings preppy vibes with a fitted bodice and flirty pleated hem. Perfect for when you want to keep it cute but still cool-girl.

    Fit & Features

    • Plaid print, knit fabric
    • Strapless neckline
    • Fitted bodice, hidden side zipper and hook-eye closure
    • Pleated skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000123

    Category Name: Preppy Rebel

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

    Product Badge:
    • Sale
  • Checkmate Vibes Plaid Hot Shorts

    Preppy, but make it spicy. These plaid hot shorts hug your curves with a comfy stretch fit that’s made for coffee runs, party nights, and everything in between.

    Fit & Features

    • Knit fabric, high stretch
    • Plaid print
    • Low-rise waist
    • Cheeky form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06503-000126

    Category Name: Preppy Rebel

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GRAY

    Available Size: M, L

    Product Badge:
    • Sale
  • Plaid About You Mini Skort

    A little preppy, a little flirty—this plaid mini skort does both. Perfect for dressing up or keeping it casual, it’s your go-to for effortless styling.

    Shop Matching Top: Plaid About You Vest Top

    Fit & Features

    • Woven fabric, moderate stretch
    • Plaid print
    • Mid-rise waist, mini bow detail
    • Side zipper with hook-eye closure
    • Mini-length overlay, fitted silhouette
    • Hidden knit fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000128

    Category Name: Preppy Rebel

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Long Sleeve Zip-Up Crop Top

    A little sporty, a little sultry—this zip-up crop top does it all. With a deep V neckline and long sleeves, it’s the perfect mix of casual comfort and effortless vibes with your favorite bottoms.

    Fit & Features

    • Rib knit stretch fabric
    • Fitted long sleeves
    • V-neckline
    • Front zip-up closure
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000363

    Category Name: Preppy Rebel

    Price: $29.90

    Availability: In Stock

    Available Color: BURGUNDY, BLACK

    Available Size: XS, S, M, L

  • Zip Me Up Off-The-Shoulder Top

    Effortlessly cool with a touch of attitude—this off-the-shoulder zip top nails that chic but not trying too hard vibe. The structured fit hugs just right while the front zipper adds that subtle, sultry edge perfect for night-out plans or casual moments.

    Fit & Features

    • Woven fabric, moderate stretch
    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Front zipper closure with double zip design
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-000177

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Chill Prep Striped V-Neck Sweater

    Classic stripes meet cute cable knit in this cropped sweater. Wear it with jeans for a relaxed vibe or dress it up with a midi skirt for a cute look.

    Fit & Features

    • Striped pattern
    • Soft cable knit fabric
    • V-neck
    • Relaxed long sleeves
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000130

    Category Name: Preppy Rebel

    Price: $32.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, L

  • Coffee Run Striped Sweater Topper

    Easy, cozy, and effortlessly cute—this striped knit sweater topper is your new go-to for errands, study sessions, or hangouts.

    Fit & Features

    • Striped pattern, knit fabric
    • Crew neckline
    • Long sleeves
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000145

    Category Name: Preppy Rebel

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Season Varsity 24 Sweater

    Sporty meets street. This varsity-inspired cropped sweater keeps it casual with a bold number graphic and cozy knit feel—made for styling with your favorite bottoms and boots!

    Fit & Features

    • Soft knit fabric
    • Crew neck
    • Long sleeves
    • Front '24' 
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000144

    Category Name: Preppy Rebel

    Price: $32.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Falling for Knits Crop Sweater

    Cozy with a little edge. This cable knit crop sweater levels up your casual days with subtle distressed accents and a cute vibe—perfect for coffee runs, study dates, or layering over slip dresses.

    Fit & Features

    • Cable knit soft fabric
    • Crew neck
    • Long sleeves
    • Cropped-length hem with distressed accents
    • Runs true to size

    Style Number/Barcode: 06005-000138

    Category Name: Preppy Rebel

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Season Chill Cable Knit Crop Sweater

    A cozy classic, reimagined for fall. This cropped cable knit sweater features a soft ribbed texture and Henley-style buttons for a laid-back yet polished feel. Pair it with high-rise denim or a mini skirt for your ultimate fall uniform.

    Fit & Features

    • Soft cable knit fabric
    • Crew neckline with henley-style buttons
    • Long sleeves
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000137

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Effortless Chic Knit Off-The-Shoulder Long Sleeve Bodysuit

    When your outfit needs a little “I didn’t try, but I did.” This off-the-shoulder knit bodysuit brings a soft, form-hugging fit with just the right touch of allure. Pair it with denim for the day or dress it up for the night—either way, it’s your go-to for instant polish.

    Fit & Features

    • Textured knit fabric, moderate stretch
    • Off-the-shoulder scoop neckline
    • Long fitted sleeves
    • Thong-cut bottom
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-000149

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK, IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Street Classic Faux Wool Coat

    Your cold-weather power piece. This faux wool double-breasted coat brings timeless tailoring and soft structure—an instant upgrade to every outfit, from latte runs to after-hours plans.

    Fit & Features

    • Faux wool fabric, sewn-in woven lining
    • Long sleeves
    • Lapel collar neckline
    • Double-breasted button closures
    • Front pockets
    • Structured silhouette
    • Runs true to size

    Style Number/Barcode: 06201-000044

    Category Name: Preppy Rebel

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Not Your Basic Grommet Sweater

    Prep meets punk in the best way possible. This grommet sweater gives classic knit energy with a rebellious twist—distressed edges, metal details, and all the attitude you need to stand out.

    Fit & Features

    • Soft knit fabric
    • Crew neckline
    • Long sleeves
    • Allover grommet accents
    • Distressed hem and cuffs
    • Runs true to size

    Style Number/Barcode: 06005-000141

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Cozy Allure Cable Knit Mini Dress

    Chic meets snuggly. This off-the-shoulder sweater dress hugs your curves with cable-knit texture while keeping things flirty and polished—perfect for autumn plans, latte runs, or cozy dinners out.

    Fit & Features

    • Cable knit fabric, moderate stretch
    • Folded off-the-shoulder neckline
    • Fitted long sleeves
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000157

    Category Name: Preppy Rebel

    Price: $42.90

    Availability: In Stock

    Available Color: CHARCOAL

    Available Size: L

  • Knit to Stun Open Back Mini Dress

    Keep your look playful and unexpected. This sweater mini dress keeps it sleek in the front, daring in the back. The cable knit keeps it cozy while the open back brings a hint of drama. perfect for fall slays.

    Fit & Features

    • Soft cable knit fabric with stretch
    • Mock neckline
    • Fitted long sleeves
    • Open back cutout design
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000161

    Category Name: Preppy Rebel

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On Repeat Crop Tank Top

    This spaghetti strap crop top is the kind of basic you’ll wear on repeat. Soft, fitted, and super versatile, it’s ready for gym days, coffee runs, or layering under your fave jacket.

    Fit & Features

    • Smooth knit stretchy fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000375

    Category Name: Preppy Rebel

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Effortless Edit Collar Knit Sweater

    Classic, cozy, and a little bit polished. This collared crop sweater gives laid-back luxe with its soft textured knit and relaxed silhouette—your go-to for everything from latte runs to weekend plans.

    Fit & Features

    • Soft texture knit fabric
    • Collared neckline
    • Long sleeves
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000171

    Category Name: Preppy Rebel

    Price: $36.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Cuddle Season Crop Sweater

    A cozy essential with a cool-girl twist. This fuzzy rib knit quarter zip sweater brings the perfect mix of soft and slouchy for those “cute but comfy” days with a coffee in hand!

    Fit & Features

    • Fuzzy rib knit fabric
    • Quarter zip-up front closure collar neckline
    • Slouchy long sleeves
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000164

    Category Name: Preppy Rebel

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN, TAUPE

    Available Size: XS, S, M, L

  • Everyday Chic Boat Neck Crop Sweater

    The definition of throw-on-and-go. This soft knit sweater keeps it classic with a boat neckline and cropped silhouette that flatters every outfit this fall and winter!

    Fit & Features

    • Soft fuzzy knit fabric
    • Long sleeves
    • Boat neckline
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000166

    Category Name: Preppy Rebel

    Price: $39.90

    Availability: In Stock

    Available Color: RAISIN

    Available Size: S, M, L

  • Snug Statement Cable Knit Crop Sweater

    Classic knit, cropped just right. This mock neck cable sweater mixes timeless texture with a modern silhouette—perfect for pairing with high-rise denim, leggings, or a little pleated mini moment.

    Fit & Features

    • Soft cable knit fabric
    • Mock neck
    • Long sleeves
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000178

    Category Name: Preppy Rebel

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NAVY

    Available Size: L

    Product Badge:
    • Sale
  • All Day Cute Striped Knit Sweater

    Stripes that never miss. This mock neck dolman sweater pairs soft knit comfort with a relaxed crop hem with slit accents that pair perfectly with fall and winter styling!

    Fit & Features

    • Striped pattern, cotton-blend knit fabric
    • Mock neck
    • Dolman long sleeves
    • Relaxed fit
    • Cropped-length hem, slit accents
    • Runs true to size

    Style Number/Barcode: 06005-000177

    Category Name: Preppy Rebel

    Price: $36.90

    Availability: In Stock

    Available Color: BLK/WHT

    Available Size: XS, S, M, L

  • Flirt Alert Plaid Lace-Up Mini Skirt

    Serving school-girl energy but make it cool girl approved. The lace-up waist and flouncy fit make this the ultimate skirt for brunch dates or casual hangs!

    Fit & Features

    • Plaid print, cotton woven fabric, stretchy knit shorts lining
    • High-rise waist
    • Front lace-up detail
    • Flouncy mini-length hem
    • Runs true to size

    Style Number/Barcode: 06303-000033

    Category Name: Preppy Rebel

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NAVY

    Available Size: S, M, L

    Product Badge:
    • Sale