Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, 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 dinner date, these casual dresses are made to move with your mood—and your calendar.
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Everyday Ease: Casual Dresses for Transitional-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. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.
Laid-Back & Versatile
Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler 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 nuetral 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!
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City After Sunset Paisley Midi Dress
A midi dress for any occasion! This strapless mesh midi dress hugs in all the right places with a moody paisley print and a flirty front slit for effortless movement and allure.
Fit & Features
- Paisley print, mesh fabric, smooth lining
- Tube strapless neckline
- Front slit
- Form-hugging fit
- Flowy midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000637
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Flirting With Florals Mini Dress
Cute enough to cause a few double takes. This floral tube mini dress hugs in all the right places with a sleek bodycon fit that’s made for brunch dates, weekend plans, and wineries.
Fit & Features
- Dainty floral print, eyelet knit-lined fabric
- Strapless tube neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000638
Category Name: Casual Dresses
Price: $33.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Sunkissed Stunner Halter Maxi Dress
Vacation mode called, and this maxi dress already answered. With a plunging halter neckline, bold cutout details, and a flowy front slit silhouette, this maxi dress was made for beachside brunches, sunny getaways, and weekend plans.
Fit & Features
- Artsy print, woven fabric
- Halter neckline
- Strappy cutout bodice, back zipper and hook-eye closure
- High front slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000645
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sweet Escape Ruffle Halter Romper
Light, sculpting, and ready for plans that turn into stories. This halter romper features a plunging neckline, ruched body, and layered ruffle detailing that deserves the spotlight.
Fit & Features
- Smooth knit fabric with high stretch
- Sleeveless plunging V-neckline
- Tie-back halter straps, open back
- Form-hugging bodice, ruched detailing
- Tiered ruffled mini-length overlay, side ruffled accents
- Hidden shorts lining
- Runs true to size
Style Number/Barcode: 06503-000231
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: WINE
Available Size: S
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Double Take Paisley Print Mesh Maxi Dress
Low back, high impact. This paisley print mesh maxi dress brings the drama with a curve-skimming fit, barely-there straps, and a draped back that keeps every exit memorable.
Fit & Features
- Paisley printed mesh fabric with knit lining, high stretch
- Sleeveless deep V-neckline, bar strap detail
- Spaghetti straps
- Open cross-back strappy design with tie closure
- Lower draped back
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000647
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: RED, BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Soft Launch Slay Off Shoulder Mini Dress
Low effort but absolutely unforgettable. This mini dress stunner hugs just right with an asymmetrical off shoulder neckline and flirty side bows that turn a simple look into a total conversation starter.
Fit & Features
- Sweater knit stretch fabric
- Off shoulder asymmetrical neckline
- Side slit accents with bow ties
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000287
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Soft Curve Alert Rib Knit Midi Dress
Warning: compliments incoming. This rib knit midi dress features a sweetheart neckline, wide shoulder straps, and a cutout back that keeps things chic, while the form-hugging fit and side slit do all the subtle showing off for you.
Fit & Features
- Soft, stretch rib knit fabric
- Sweetheart neckline
- Wide shoulder straps
- Cutout back
- Side slit
- Form-hugging, midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000660
Category Name: Casual Dresses
Price: $24.90
Availability: Out of Stock
Product Badge:- Ships Free
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Play It Bold Lace Up Romper
A little daring, a lot intentional. This leopard multi print romper mixes mesh fabric and a lace-up sweetheart neckline with built-in knit stretchy shorts, giving you drama up top and comfort underneath.
Fit & Features
- Leopard multi-print mesh fabric
- Studded sweetheart neckline with lace-up front
- Adjustable spaghetti straps
- Drop waist seam
- Ruffled skirt overlay, stretchy knit shorts lining
- Runs true to size
Style Number/Barcode: 06503-000217
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M
Product Badge:- Best Seller
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Alluring Chic Ribbed Knit Belted Mini Dress
Confident curves, chic allure. This ribbed knit mini dress hugs in all the right places with a belted waist that pulls the look together for nights out, date plans, or anytime you want effortless polish with a little edge.
Fit & Features
- Ribbed knit fabric with high stretch
- Sleeveless scoop neckline
- Tie-back halter straps, partially open back
- Attached O-ring belt detail at the waist
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000283
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: S, M, L, XS
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Gallery After Hours Cowl Neck Midi Dress
It’s giving art opening energy, but make it wearable. This artsy abstract print midi dress features a draped cowl neckline, delicate spaghetti straps, and a front slit on a form-hugging silhouette that feels equal parts effortless and elevated.
Fit & Features
- Abstract print, knit-lined stretch fabric
- Cowl neckline, Adjustable spaghetti straps
- Front slit
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000661
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: S
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Serving Chic Halter Cutout Bodycon Midi Dress
Serving subtle drama with zero effort. This halter bodycon midi dress sculpts your shape with ribbed stretch and bold cutouts—made for nights when you want to feel chic and a little daring.
Fit & Features
- Hacci ribbed knit-lined fabric, high stretch
- Sleeveless crew neckline
- Halter tie-back straps, open back
- Waist cutouts leading to an open lower back
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000666
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Sultry Vibe Paisley Print Bodycon Maxi Dress
The kind of dress that does all the talking the second you walk in. This paisley print bodycon maxi dress skims your shape with a soft, sculpting stretch—perfect for sultry nights out.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Paisley print
- Sleeveless square neckline
- Adjustable spaghetti straps
- High-cut side slit
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000664
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Soft Curve High Slit Midi Tube Dress
Serving soft curves with a little edge—this one knows exactly what it’s doing. The midi tube dress hugs in all the right places with a high slit that makes every step feel intentional.
Fit & Features
- Ribbed cotton-blend knit fabric, high stretch
- Strapless sweetheart neckline, knot-front design
- High-cut side slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000665
Category Name: Casual Dresses
Price: $22.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet On Arrival Floral Skater Dress
Sweet, light, and made for daytime plans. This strapless skater dress features a soft sweetheart neckline and delicate floral details that feel easy and feminine, perfect for brunch dates, bridal celebrations, and plans that turn into golden hour.
Fit & Features
- Ditsy floral print, woven fabric
- Strapless sweetheart neckline with delicate trim
- Skater silhouette with pleating
- Mini-length flared hem
- Runs true to size
Style Number/Barcode: 05101-000956
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: M, L
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Sun Chasing Ribbed Knit Halter Midi Dress
Hot plans? Found the dress. This ribbed knit halter bodycon midi dress hugs in all the right places with a ruched bust and flirty keyhole cutout—aka your go-to for birthday dinners, rooftop nights, and every RSVP in between.
Fit & Features
- Ribbed sweater knit fabric, high stretch
- Sleeveless sweetheart neckline
- Tie-back halter spaghetti straps
- Ruched bust, keyhole cutout
- Midi-length hem, high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000286
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BANANA
Available Size: S, M, L
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Picture Perfect Lace Trim Floral Woven Skater Dress
You booked the brunch. Now match the vibe. This lace trim floral lace-up skater dress snatches at the corset bodice and flares into a twirl-ready mini made for parties, day dates, and every camera roll moment in between.
Fit & Features
- Floral printed woven fabric with lining, dainty lace trims
- Strapless straight-across neckline, ruched bust, tie detail
- Corset-style bodice, V-shaped drop waist
- Lace-up back design, tie closure
- Mini-length skater silhouette, pleated detailing
- Runs true to size
Style Number/Barcode: 05101-000973
Category Name: Casual Dresses
Price: $64.90
Availability: In Stock
Available Color: LAVENDER
Available Size: XS, S, M, L
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Vacay Mood Tropical Floral Halter Skater Dress
Booked, busy, and dressed like it. This tropical floral halter skater dress hugs just enough up top, then flares into a playful, twirl-ready silhouette made for plans that don’t end early.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless plunging V-neckline, bar strap with beaded accents
- Halter tie-back straps
- Open back, lower tie-back spaghetti straps
- Tiered ruffled design, mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000674
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: FUCHSIA
Available Size: XS, S, M, L
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Extra Flirty Ruffle Mini Dress
This is the mini dress you wear when you want something a little extra. The plunging halter neckline, open back, and ruched drop waist hugs your curves, while the tiered ruffle skirt keeps it flirty for parties, birthdays, and spontaneous nights out.
Fit & Features
- Smooth knit fabric with high stretch
- Sleeveless plunging V-neckline
- Tie-back halter straps, open back
- Ruched drop waist
- Tiered ruffled design
- Mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-001026
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: WHITE, WINE
Available Size: XS, S, M, L
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Charming Babe Bow And Floral Print Skater Dress
Soft florals, sweet bows, and a neckline made to flatter—this one feels instantly charming. The V-shaped drop waist and flutter sleeves keep it light, feminine, and perfect for brunch plans, daytime dates, and photo ops.
Fit & Features
- Poplin woven fabric, delicate lace trim detailing
- Bow and floral print
- Flattering V-neckline
- Short flutter sleeves
- Button-down front, V-shaped drop waist
- Short skater silhouette, pleated detailing
- Runs true to size
Style Number/Barcode: 05101-000768
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, L
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Flirty Flare Polka Dot A-Line Mini Dress
Both flirty and impossible to ignore. This polka dot mini dress hugs in all the right places before flaring into an easy A-line fit that’s made for dinner dates, rooftop plans, and drinks with the girls.
Fit & Features
- Smooth knit fabric, high stretch
- Polka dot print
- Sleeveless deep V-neckline
- Adjustable spaghetti straps
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000679
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Cutest Plans Floral Eyelet Corset Skater Dress
Your group chat is already asking where you got it. This floral eyelet corset skater dress cinches you in with a sculpted bodice and flares out into the cutest twirl-ready silhouette for brunch dates, garden parties, and every camera roll moment in between.
Fit & Features
- Floral eyelet woven fabric, tulle and knit linings
- Sleeveless sweetheart neckline, ruched bust, small cutout, tie-front detail
- Underwire bust support
- Tie-shoulder straps, side zipper and hook-eye closure
- Corset bodice with boning, V-shaped waist, ruffled trim
- Lace-up back design, short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000130
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
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Twice As Nice Halter Ruffle Mini Dress
Date night just found its favorite dress. This halter mini dress serves a plunging neckline and a tiered ruffle skirt that moves with you from cocktails to the dancefloor.
Fit & Features
- Lace-lined fabric
- Plunge halter neckline
- Open back
- Form-hugging fit
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000816
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M
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Sunny Plans Striped Crochet Strapless Mini Dress
Sunny plans, cute outfit, and you’re already out the door. This striped crochet mini dress hugs just right up top with a strapless fit and flares into an easy A-line that’s made for brunch, beach days, and last-minute invites.
Fit & Features
- Striped crochet knit fabric with knit lining, moderate stretch
- Strapless straight-across neckline, no-slip strip
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000689
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Obsessed Already Eyelet Knit A-Line Mini Dress
This one just does something to your confidence. The eyelet knit A-line mini dress hugs up top, flares just right, and feels like an easy yes for anything on your calendar.
Fit & Features
- Eyelet knit fabric with knit lining, high stretch
- Sleeveless sweetheart neckline, ruched bust
- Adjustable spaghetti straps
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000690
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
Product Badge:- Best Seller