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.

  • Cozy Edit Crop Sweater

    Soft, simple, and seriously versatile. This cropped pullover sweater features a cozy, ribbed texture and a relaxed fit that pairs perfectly with your favorite bottoms and boots for an effortlessly chic look.

    Fit & Features

    • Soft rib knit stretchy fabric 
    • Crew neckline
    • Relaxed long sleeves, rib knit cuffs
    • Relaxed fit
    • Side slit accents
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000188

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY, DENIM

    Available Size: S, M, L, XS

  • Autumn Stroll Striped Corduroy Shorts

    Cooler weather, cozier textures—these striped corduroy shorts are made for layering with knits and boots. A comfy-meets-chic staple for all your fall plans.

    Fit & Features

    • Striped pattern, corduroy fabric
    • Low-rise waist
    • Form-hugging fit
    • Front button closure, belt loop accents
    • Back pockets
    • Runs true to size

    Style Number/Barcode: 06303-000038

    Category Name: Preppy Rebel

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: L

    Product Badge:
    • Sale
  • Glam Code Patent Slingback Heels

    Classic with a little sparkle. These patent slingback heels feature a sleek pointed toe and rhinestone buckle detail that instantly elevates any look—from boardroom days to after-hours drinks.

    Fit & Features

    • 3" Stiletto heel
    • Closed pointed-toe 
    • Rhinestone-embellished buckle accent
    • Slingback ankle strap
    • Luxe fit cushioned insole
    • Patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000515

    Category Name: Preppy Rebel

    Price: $36.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Final Touch Buckle Stiletto Pumps

    She means business—with a side of glam. These patent slingback pumps feature bold buckle grommet details and a sleek stiletto silhouette that instantly sharpens any look from day to night plans.

    Fit & Features

    • 3.5" Stiletto heel
    • Closed pointed-toe
    • Buckle and studded embellishments
    • Slingback adjustable ankle strap, buckle closure
    • Cushioned insole
    • Patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000516

    Category Name: Preppy Rebel

    Price: $36.90

    Availability: In Stock

    Available Color: WINE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Polished Mood Double Breasted Trench Coat

    This faux wool coat brings instant polish — a clean double-breasted front, long tailored lines, and that “I planned this outfit” energy even when you absolutely didn’t. It’s warm enough for crisp days and chic enough for every coffee run, commute, or night out.

    Fit & Features

    • Faux wool fabric, sewn-in lining
    • Notched lapel collar
    • Long sleeves with button-detail cuffs
    • Double-breasted front with button closures
    • Side welt pockets
    • Longline tailored silhouette
    • Runs true to size

    Style Number/Barcode: 06201-000061

    Category Name: Preppy Rebel

    Price: $79.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free
  • Catch Feelings Plaid Pleated Skort

    She’s sweet, but she’s not subtle. This skort knows how to turn a hallway into a runway—with flirty pleats and lace-up sides that do all the flirting for you.

    Fit & Features

    • Plaid print, woven fabric
    • Mid rise waist
    • Dual side tie accents
    • Pleated mini skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06303-000031

    Category Name: Preppy Rebel

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Polish High-Rise Flare Trouser Pants

    Sleek, sculpted, and made to move with you. These high-waist flare pants blend polished tailoring with a flattering seam detail—perfect for dressing up your 9-to-5 or elevating your weekend look.

    Fit & Features

    • Smooth woven fabric
    • High-rise waist, belt loop accents
    • Hidden front zipper and hook-eye fasteners
    • Hip-hugging fit
    • Seam detailing down the front
    • Flare hem
    • Runs true to size

    Style Number/Barcode: 06402-000012

    Category Name: Preppy Rebel

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Preppy Play Plaid Bloomer Shorts

    These plaid bloomer shorts give lounge-meets-street vibes with their relaxed fit and gathered hem—perfect for pairing with an oversized tee, chunky sweater, or your “just rolled out but still cute” mood.

    Fit & Features

    • Plaid print, chiffon fabric, sewn-in woven lining
    • Mid-rise waist with bow accent
    • Smocked form-hugging silhouette
    • Ruffled trim hem
    • Runs true to size

    Style Number/Barcode: 06503-000162

    Category Name: Preppy Rebel

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Effortless Off-Duty Faux Leather Cabby Hat

    Meet the hat that instantly upgrades your outfit. With its sleek faux leather finish and structured cabby silhouette, this piece brings that effortless off-duty polish that looks perfectly put together without even trying.

    Fit & Features

    • Faux leather material
    • Classic cabby hat design
    • Flat top
    • Short curved brim
    • Side button accents

    Style Number/Barcode: 07302-000163

    Category Name: Preppy Rebel

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Stride Micro Suede Sneakers

    Cool, comfy, and city-ready—these microfaux suede sneakers feature sleek faux leather side stripes and a rubber traction sole that’s made for moving. Perfect for errands, off-duty looks, or casual hangs.

    Fit & Features

    • Square toe
    • Lace-up front placket
    • Faux leather side-striped design
    • Rubber traction bottom
    • Micro faux suede material
    • Runs true to size

    Style Number/Barcode: 07405-000014

    Category Name: Preppy Rebel

    Price: $32.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Falling For Layers Crop Knit Sweater

    Sweater weather, but make it cute. This cropped knit sweater is your go-to for layered fall looks—perfect for classes, coffee dates, or strolls through the farmer’s market.

    Fit & Features

    • Soft knit fabric with stretch
    • Crew neck
    • Long sleeves
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000200

    Category Name: Preppy Rebel

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Checked Out Button-Up Cardigan

    Your not-so-basic cardigan moment. This checkered knit button-up cardigan nails that oversized, effortlessly thrown-on vibe—perfect for coffee runs, cozy hangs, or layering over your fave basics.

    Fit & Features

    • Checkered pattern, soft knit fabric
    • Relaxed long sleeves, ribbed cuffs
    • Button-up front closures
    • Runs oversized

    Style Number/Barcode: 06005-000208

    Category Name: Preppy Rebel

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Agenda Crew Neck Knit Sweater

    Your PSL’s new BFF. With a classic crew neck and soft knit feel, this sweater was made for crisp air, latte runs, and all the pumpkin patches!

    Fit & Features

    • Soft knit fabric with stretch
    • Ribbed crew neck
    • Long sleeves with ribbed cuffs
    • Relaxed fit
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000202

    Category Name: Preppy Rebel

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Up Cable Knit Cardigan

    This chunky cable knit cardigan is cropped, cozy, and made for layering. Perfect for crisp fall mornings, coffee runs, and everything in between.

    Fit & Features

    • Chunky cable knit design
    • Relaxed long sleeves
    • Open front design
    • Relaxed cropped length hem
    • Runs true to size

    Style Number/Barcode: 06005-000263

    Category Name: Preppy Rebel

    Price: $12.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vintage Cool Cropped Moto Jacket

    Layer on instant vintage-inspired cool. This cropped moto adds that polished toughness that pulls a look together fast—structured enough to feel intentional, relaxed enough to throw on and go.

    Fit & Features

    • Glossy faux leather fabric, sewn-in smooth woven lining
    • Notched collar neckline with asymmetric zip front
    • Long sleeves 
    • Faux zipper pockets
    • Cropped silhouette with adjustable belt detail
    • Runs true to size

    Style Number/Barcode: 06204-000088

    Category Name: Preppy Rebel

    Price: $59.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Flirt Mode Faux Leather Skort

    Equal parts fierce and flirty. This faux leather skort serves attitude with a ruffled tiered design and a short, flattering fit—your go-to for a concert or a bold day look.

    Fit & Features

    • Sleek faux leather fabric, stretchy knit shorts lining
    • High-rise waist
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000093

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • City Flirt Polka Dot Halter Top

    This halter top turns classic polka dots into a modern moment with its high neckline, cowl drape, and open back tie—perfect for dinner dates, city strolls, and spontaneous mimosa brunches!

    Fit & Features

    • Polka dot print, knit stretchy fabric
    • High halter neckline with tie closure
    • Cutout front bust
    • Open strappy back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000344

    Category Name: Preppy Rebel

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

  • Time After Time Layered Necklace

    Bold meets timeless. This layered necklace mixes multiple chain styles with luxe charms—including a statement watch pendant—for a stacked look that does the most with minimal effort.

    Fit & Features

    • Multi-layered chain designs
    • Watch charm with adjustable side dial
    • Mixed charms
    • Lobster clasp closure

    Style Number/Barcode: 07007-000071

    Category Name: Preppy Rebel

    Price: $24.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • On Repeat Twist Front Top

    Simple but never basic. This long sleeve twist front top gives your outfit that effortless, elevated edge—perfect for pairing with denim, minis, or anything that deserves a confident upgrade.

    Fit & Features

    • Soft stretch knit fabric
    • Deep V-neckline, fitted long sleeves
    • Front twist knot detail
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000354

    Category Name: Preppy Rebel

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Soft Spoken Ribbed Crop Top

    A soft staple with just the right touch of flirty. This ribbed knit crop top features a foldover off-shoulder neckline and a fitted silhouette made for pairing with skirts, shorts, or your favorite denim.

    Fit & Features

    • Soft rib knit stretchy fabric
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000460

    Category Name: Preppy Rebel

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN, IVORY

    Available Size: XS, S, M, L

  • Sweet Talk Polka Dot Crop Top

    Vintage flirt meets modern cool. This polka dot hook-and-eye top brings all the retro charm with a curve-hugging fit and scalloped edges—made for pairing with low-rise pants, mini skirts, or your favorite weekend latte.

    Fit & Features

    • Polka dot print, knit stretch fabric
    • Halter plunge neckline
    • Front hook-eye closures
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000360

    Category Name: Preppy Rebel

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Polished Prep Patent Loafers

    These patent loafers bring a sleek, polished vibe to your everyday rotation. Glossy and structured with that classic preppy shape, they turn even a jeans-and-sweater day into something effortlessly put-together.

    Fit & Features

    • Square toe design
    • Classic penny strap detail
    • Cushioned footbed for all-day wear
    • Low-profile sole with sturdy traction
    • Glossy patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07405-000024

    Category Name: Preppy Rebel

    Price: $26.90

    Availability: In Stock

    Available Color: WINE, BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Plaid About You Vest Top

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

    Shop Matching Bottoms: Plaid About You Mini Skort

    Fit & Features

    • Woven fabric with knit lining, moderate stretch
    • Plaid print
    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Button-down front
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000048

    Category Name: Preppy Rebel

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Tailored Mood Plaid Woven Shorts

    Your “I planned this” shorts—clean, tailored, and instantly elevated. The plaid woven finish gives them that strategic, cool-girl polish that works from brunch to late-night plans without ever trying too hard.

    Shop Matching Blazer: Tailored Mood Plaid Woven Blazer

    Fit & Features

    • Plaid printed woven fabric
    • Mid-rise waist, belt loops
    • Front closure
    • Dual front pockets
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06403-000065

    Category Name: Preppy Rebel

    Price: $15.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Sale