Casual dresses that keep up with your plans—brunch, game day, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and sweater knits, these pieces prove laid-back can still look styled. Play it polished with a shirt dress or belted A-line, lean comfy-cute in a fitted bodycon, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute outing, these casual dresses are built to move with your mood—and your calendar.

Show filters

Sort:

Size

Color

Price

All filters

Sort

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); } }) })

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

Everyday Ease: Casual Dresses for Cool-Weather Plans

From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends.

Laid-Back & Versatile

Knit, ribbed, and sweater dresses bring comfort and style to crisp fall days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in burgundy or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.

Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.

What Makes a Dress Casual?

Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.

Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.

How Do I Style a Dress Casually?

Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.

For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!

Elevated Chic Off-The-Shoulder A-Line Mini Dress
Elevate any casual day in this off-the-shoulder mini dress! This stunning dress features a twisted bust accent for a trendy touch, an A-line silhouette, and a mini-length hem that creates a flattering fit on the smooth knit-lined fabric. Complete the look with luxe earrings for a dinner party!

Fit & Features
- Smooth knit lined fabric, moderate stretch
- Off-the-shoulder neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5755

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Moment Off-The-Shoulder Bell Sleeve Mini Dress
An off-the-shoulder mini dress that'll give you many chic moments! The crepe dress is designed with long fitted bell sleeves with flirty tie accents and a front slit for movement. Complete the look with a necklace.

Fit & Features
- Viscose crepe knit fabric with knit lining, moderate stretch
- Off-the-shoulder sweetheart neckline, can be worn on the shoulder
- Long fitted bell sleeves, tie accents
- Front slit
- Mini-length hem
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5881

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual Muse Scoop Neck Mini Dress
A casual mini dress that's sure to become your fashion muse! The mini-length dress features fitted long sleeves, a scoop neckline, a built-in shelf bra for extra support, and a flattering bodycon silhouette on stretchy rib knit fabric. Complete the look in a moto jacket and boots for day or evening plans!

Fit & Features
- Fitted long sleeves
- Scoop neckline
- Built-in shelf bra
- Bodycon silhouette, mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5244

Category Name: Casual Dresses

Price: $19.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Standout Staple Crew Neck Cutout Midi Dress
This midi dress may just become that special staple piece in your lineup! It features fitted long sleeves, a crew neck with a button-back closure and keyhole accent, a flattering bodycon silhouette and front slit, and a flirty cutout back design. Complete the look with statement earrings for a cocktail hour.

Fit & Features
- Fitted long sleeves
- Crew neck, back button closure, keyhole
- Bodycon silhouette, front slit
- Cutout back design
- Soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5335

Category Name: Casual Dresses

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek Silhouette Ribbed Knit Off-The-Shoulder Midi Dress
Showcase a sleek silhouette in this ribbed knit midi dress featuring an off-the-shoulder neckline with a fold-over design and a mermaid silhouette to highlight your curves. Style with knee-high boots for a chic look.

Fit & Features
- Ribbed knit fabric, plenty of stretch
- Off-the-shoulder neckline
- Fold-over design, short sleeves
- Midi-length mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5896

Category Name: Casual Dresses

Price: $14.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Simply Amazing Long Bell Sleeve Mini Dress
A simply amazing little black dress you'll adore wearing on dressy occasions! It features a square neckline, long bell sleeves with trendy ruched adjustable ties and slit accents, a flattering bodycon silhouette, and a mini-length hem. The dress is composed of a double-lined soft brushed knit fabric. Complete the look with a chic mini purse and heels.

Fit & Features
- Double-lined soft brushed knit fabric
- Moderate stretch
- Square neckline
- Long bell sleeves, ruched adjustable ties, slit accents
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5318

Category Name: Casual Dresses

Price: $5.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Endlessly Effortless Crew Neck Abstract Midi Dress
You'll always look and feel perfect in this sleeveless midi dress for parties or going out! Crafted from an abstract print mesh fabric, this dress boasts a crew neckline, a flattering bodycon silhouette, and a midi-length hem. Complete the look in stiletto heels and a purse!

Fit & Features
- Abstract print, mesh fabric, soft knit lining
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5819

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Expression Sleeveless Plaid Mini Dress
A sleeveless plaid mini dress features a flattering square neckline with a satin bow, shoulder straps, and a bodycon silhouette. Perfect for back-to-school styling.

Fit & Features
- Plaid woven fabric, bust lining, minimal stretch
- Square neckline with satin bow
- Shoulder straps
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5825

Category Name: Casual Dresses

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Lost In Love Strappy Back A-Line Mini Dress
Everyone will be lost in love once they catch sight of you in this strappy A-line mini dress! Perfect for any occasion, this dress will have you feeling fabulous. This playful A-line mini features a flattering sweetheart neckline, shoulder straps for added support, and a strappy back for flirty fun. Complete the look in block heels.

Fit & Features
- Smooth knit fabric lined with stretchy knit
- Sweetheart neckline
- Shoulder straps
- Strappy back
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5544

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chicly Femme Bodycon Abstract Mesh Midi Dress
A sleeveless midi dress features a square neckline and a bodycon silhouette that flaunts your curves. The abstract print mesh fabric offers an artsy look. Perfect for styling with stilettos.

Fit & Features
- Abstract print, mesh fabric
- Square neckline
- Spaghetti straps
- Bodycon midi-length fit
- Runs true to size
Style Number/Barcode: 05102-5580

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stunning Sweetie Open Back Bow Skater Dress
Arrive like the stunning sweetie you are in this short skater dress as the bride-to-be, graduate, or birthday girlie! This dress features a square neckline and shoulder straps, with an attention-grabbing open back and statement bow detail. The drop waist skater silhouette is flattering, and the short-length hem is perfect for showing off your legs. Complete the look in block heels.

Fit & Features
- Woven fabric, tulle and stretchy knit lining
- Square neckline, shoulder straps
- Open back, statement bow
- Back zipper and hook-eye closure
- Drop waist seam, skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3410

Category Name: Casual Dresses

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Colorful Essence Sleeveless Marble Print Mini Dress
You'll be the most colorful babe on the scene in this marble print mini dress! Perfect for art gallery openings and date nights, this sleeveless dress boasts a square neckline, adjustable spaghetti straps for a custom fit, and side ruched seams and a bodycon fit to accentuate your curves. Complete the look with a clutch and stiletto heels.

Fit & Features
- Marble print, mesh fabric, sewn-in knit lining, moderate stretch
- Square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5691

Category Name: Casual Dresses

Price: $42.90

Availability: Out of Stock
Product Badge:
- Sale
Easy Bliss Turtleneck Striped Mini Dress
This sleeveless knit mini dress boasts a turtle neckline and a bodycon silhouette with a trendy striped pattern. Style with simple hoop earrings for any casual plans.

Fit & Features
- Striped pattern, stretchy knit fabric
- Turtle neckline
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 06005-2045

Category Name: Casual Dresses

Price: $7.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Smooth Silhouette Long Sleeve Ruched Mini Dress
Embrace your curves in this must-have mini dress! The short dress features fitted long sleeves and a scoop neckline for a flattering look, while the side ruched seams and bodycon silhouette accentuate your curves. Crafted from a double-lined buttery soft fabric that fits like a glove with plenty of stretch. Layer with a jacket and a trendy shoulder bag to complete the look!

Fit & Features
- Fitted long sleeves
- Scoop neckline
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Double-lined buttery soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5519

Category Name: Casual Dresses

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Luxe Long Sleeve Ribbed Knit Mini Dress
Part casual, part luxe, this long-sleeved mini dress is perfect for your next date night! The ribbed knit dress features a square neckline, long sleeves, and a mini-length hem. Complete look with knee-high boots!

Fit & Features
- Ribbed knit fabric with knit lining, plenty of stretch
- Square neckline
- Long fitted sleeves
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5899

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Carefree Chic Long Sleeve Ribbed Knit Midi Dress
An off-the-shoulder midi dress perfect for those carefree days! It features fitted long sleeves and a bodycon fit that shows off your curves. Pair with sneakers.

Fit & Features
- Ribbed knit fabrication, stretchy knit lining
- Off-the-shoulder neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5924

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cute Flirt Drop Waist Ruffled Hem Mini Dress
Show off your stunning figure in this smooth knit mini dress featuring a boat neckline, long fitted sleeves, a cute scoop back, a drop waist design, and a short tiered ruffled hem with an A-line fit for that flirty flair. Style with strappy mules!

Fit & Features
- Smooth nylon knit fabric, plenty of stretch
- Boat neckline
- Long fitted sleeves
- Scoop back
- Drop waist
- Tiered ruffled mini-length hem, A-line fit
- Runs true to size
Style Number/Barcode: 05102-5938

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Serving Chic Long Bell Sleeve A-Line Mini Dress
Serve chic looks in this A-line mini dress featuring a halter V-neckline with flirty cutouts and long fitted bell sleeves to give coverage. Style with earrings.

Fit & Features
- Smooth knit fabric with partial lining, plenty of stretch
- Halter V-neckline, tie-back spaghetti straps
- Cutout shoulder design
- Long fitted bell sleeves, slit accents
- Lower back cutout
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3657

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Raise The Bar Ribbed Knit High Slit Midi Dress
Raise the bar in this knit high slit midi dress boasting a sultry off-the-shoulder neckline and a form-hugging fit. Pair with boots.

Fit & Features
- Ribbed knit fabric, plenty of stretch
- Off-the-shoulder neckline
- Fold over accent at bust
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2081

Category Name: Casual Dresses

Price: $7.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bold Allure Abstract Print Mesh Midi Dress
Show up and stun in this airy mesh midi dress accented with a trendy abstract print for a bold allure. The dress features a crew neckline, short cap sleeves, and a form-hugging silhouette to highlight your curves.

Fit & Features
- Abstract printed sheer mesh fabric with partial knit lining, plenty of stretch
- Lettuce edge hems
- Crew neckline
- Short cap sleeves
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5628

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Adorable Drop Waist Bubble Hem Skater Dress
Adorable and trendy will be your vibe in this soft knit skater dress featuring a mock neckline, tank shoulder straps, ruched side seams to accentuate your curves, and a short ruched bubble hem. Style with platform heels for a cute party look!

Fit & Features
- Double-lined brushed knit fabric, plenty of stretch
- Mock neckline, tank shoulder straps
- Ruching
- Drop waist seam
- Short skater silhouette
- Ruched bubble hem
- Runs true to size
Style Number/Barcode: 05102-5902

Category Name: Casual Dresses

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Alluring Moment Faux Suede Lattice Cutout Mini Dress
Fit & Features
- Faux suede fabric with knit lining, moderate stretch
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper with hook-eye closure
- Dual lattice side cutouts at bodice and waist
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5782

Category Name: Casual Dresses

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Marvelous Blooms Lace-Up Corset Floral Skater Dress
Stay stunning all night in this floral skater dress at prom, birthdays, or dressy events! With adjustable spaghetti straps and a drawstring sweetheart neckline, this dress offers a perfect fit every time. The underwire bust, flexible boning, and a lace-up back provide support and a flattering silhouette, while the mini-length hem adds a playful touch. Complete the look in chic block heels.

Fit & Features
- Floral print, woven fabric, woven lining, no stretch
- Adjustable spaghetti straps
- Drawstring sweetheart neckline
- Side zipper and hook-eye closure
- Underwire bust
- Flexible boning, lace-up back
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3550

Category Name: Casual Dresses

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sealed With Charm Ponte Mini Dress
Seal your style with this charming ponte mini dress featuring an adorable strapless sweetheart neckline with a bow and a bodycon fit. Style with earrings.

Fit & Features
- Ponte knit fabric, plenty of stretch
- Strapless sweetheart neckline
- Bow tie front accent
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5897

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

Reset Your Password

Email Sent

Order Status

Casual Dresses

HomeCasual Dresses

Product Recommendations