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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Spice Done Right Mesh Midi Dress
Too good to save for just one occasion. This mesh midi dress hugs every curve with ruched detailing and a strapless neckline that makes the whole dress feel a little extra in the best way.
Fit & Features
- Mesh-lined fabric
- Strapless sweetheart neckline
- Back zipper closure
- Bodycon silhouette, ruched detail
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000588
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
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Daydream Detour Paisley Maxi Dress
Easy, floaty, and somehow always the prettiest thing in your closet. This floral paisley maxi dress features a flowy silhouette, lace trim details, and an open tie back that feels made for brunch, weekend markets, and sunny day plans.
Fit & Features
- Floral paisley print, woven fabric, short woven lining
- V-neckline, spaghetti straps
- Open tie-back
- Center front button-up closures
- Flowy maxi silhouette, sheer lace trim
- Runs true to size
Style Number/Barcode: 05102-000592
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Simple Charm Gingham Mini Dress
Feels like a picnic invite just showed up. This gingham mini dress keeps it cute and easy with a collar, cap sleeves, and a button-down front that works from coffee shop hangs to casual plans.
Fit & Features
- Gingham pattern, cotton-blend woven fabric, woven lining
- Collar neckline
- Cap sleeves
- Front button-down closures
- Tie-back strap
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000598
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Effortless Confidence Sheer Lace Maxi Dress
A little sheer, a little bold—exactly how you like it. This lace maxi dress skims your body with a soft stretch feel, made for slipping into when the vibe calls for effortless confidence.
Fit & Features
- Textured lace fabric with a mini-length knit lining, moderate stretch
- Sleeveless V-neckline with O-ring accent at the bust
- Adjustable spaghetti straps
- Maxi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000599
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Golden Hour Crochet Halter Dress
Booked for golden hour and not coming back early. This crochet halter mini dress features floral appliqué and a lace-up back that keeps things effortlessly pretty with just enough detail to stand out.
Fit & Features
- Crochet texture-lined knit fabric
- Halter plunge neckline with beaded strap
- Open back with lace-up design
- Floral applique
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000605
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Island Nights Mesh Halter Maxi Dress
Vacay booked. This tropical mesh maxi dress brings that breezy, curve-skimming fit with a trendy ruffled slit that moves with you from beach cocktails to dinner.
Fit & Features
- Tropical print, mesh fabric, soft knit lining
- Halter V-neckline with hardware insert
- Tie straps, open back
- High front ruffled slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000607
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Vacation Flirt Knit Cutout Maxi Dress
Serving vacation flirt and trendy vibes. This knit maxi dress hugs in all the right places with lace-up cutouts, a plunging halter neckline, and an open back that knows exactly what it’s doing.
Fit & Features
- Knit fabric with flame stitch pattern
- Sleeveless plunging V-neckline, beaded strap
- Tie-back halter straps
- Lace-up side cutouts
- Open back, lower tie-back spaghetti straps
- Maxi-length bodycon silhouette, back slit accent
- Runs true to size
Style Number/Barcode: 05102-000606
Category Name: Casual Dresses
Price: $48.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Love At First Glance Long Sleeve Bodycon Mini Dress
This one knows exactly what it’s doing. A long sleeve bodycon mini dress with a scoop neckline and button cutout that hugs close, highlights just enough, and feels made for date nights and Valentine’s plans.
Fit & Features
- Textured stretch knit fabric
- Scoop neckline
- Fitted long sleeves
- Front cutout detail
- Decorative button accents
- Mini length hem
- Runs true to size
Style Number/Barcode: 06005-000276
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Alluring Off-The-Shoulder Cutout Midi Dress
Dinner plans, last call, encore moment—this dress says yes to all of it. The off-the-shoulder neckline and front cutout keep things confident, elevated, and unforgettable.
Fit & Features
- Textured ribbed knit fabric, high stretch
- Off-the-shoulder neckline
- Long fitted sleeves
- Front cutout with hardware button details
- Bodycon silhouette
- Midi-length hem, high-cut side slit
- Runs true to size
Style Number/Barcode: 06005-000279
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Textured ribbed knit fabric, high stretch
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Raise A Toast Mesh Bodycon Midi Dress
Made for wedding invites, cocktail receptions, and the kind of nights that deserve extra photos. This strapless mesh midi dress sculpts your figure with flattering ruching and a draped side sash that brings the drama.
Fit & Features
- Mesh-lined fabric
- Strapless neckline
- Wrap side sash detail
- Back zipper closure, center back slit accent
- Ruched bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001186
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: LIGHT, BLUE-2
Available Size: XS, S, M, L, XL
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Weekend Flare Paisley Skater Mini Dress
Your weekend lineup just got cuter. This paisley mesh skater dress features delicate straps and a flowy tiered hanky hem that moves with every step, making it an easy pick for any sunny day plans.
Fit & Features
- Paisley print, mesh-lined fabric
- V-neckline
- Adjustable spaghetti straps
- Flowy skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000610
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS
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Garden Party Glow Floral Halter Midi Dress
Soft, sweet, and lowkey stealing all the attention. This floral halter midi dress hugs just right with a flattering fit that’s perfect for brunch plans, date nights, or any last-minute invite.
Fit & Features
- Lightweight eyelet fabrication with soft lining
- Sleeveless halter neckline
- Delicate floral pattern
- Fitted bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000609
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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After Hours Bloom Floral Burnout Mesh Mini Dress
Flirty with a side of intention—this one moves differently. The floral burnout mesh mini dress hugs up top, flows below, and shows up perfectly for plans that turn into after-hours moments.
Fit & Features
- Lined mesh fabric with floral burnout texture
- Strapless neckline, tube silhouette with a fitted bodice
- Drop waist with tiered ruffle mini skirt for movement
- Runs true to size
Style Number/Barcode: 05101-000999
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Stunner Mesh Strapless Midi Dress
Hot plans, zero overthinking—this dress just gets it. A sleek strapless mesh midi that hugs in all the right places and shows up ready for every RSVP on your calendar.
Fit & Features
Style Number/Barcode: 05102-000611
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Soft Spoken Statement Linen V Neck Maxi Dress
Quiet luxury, but make it cool girl. This linen V-neck maxi dress skims the body with an easy drape, delicate straps, and lace panel details that feel effortless for dinner plans, gallery nights, or that last-minute RSVP.
Fit & Features
- Lightweight linen blend fabrication
- Sleeveless v-neckline
- Adjustable spaghetti straps
- Lace panel inserts
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000614
Category Name: Casual Dresses
Price: $64.90
Availability: In Stock
Available Color: BLACK, WHITE
Available Size: S, M
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Spritz And Plans Strapless Mini Dress
This dress has "take me on vacay" written all over it! The playful print and easy strapless fit keep it light, while the flowy mini hem makes it perfect for enjoying a sunny day on your next getaway.
Fit & Features
- Garden fruit and veggie print, woven fabric, stretchy knit lining
- Strapless neckline, stretchy smocked bodice
- Fit and flare silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000617
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Unforgettable Entrance Plunge Neck Maxi Dress
This maxi dress doesn’t blend in—it arrives. This plunging cowl neck maxi dress drapes smoothly through the body with a halter neckline that feels bold, polished, and intentionally striking. Pair with heels for date night, dressy celebrations, or a sultry vacation look.
Fit & Features
- Smooth knit-lined fabric with high stretch
- Halter neckline with plunging cowl front
- Open back with adjustable tie closure
- Fitted bodice that skims the waist and hips
- High side slit for movement
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000736
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay State Of Mind Tropical Print Maxi Dress
Vacation state of mind, no passport required. This tropical print maxi dress hugs you in all the right places with a sleek bodycon fit and bold cutout details that feel both effortless and elevated.
Fit & Features
- Knit fabric with high stretch, soft knit lining
- Tropical print
- Strapless neckline
- Triple bust cutouts and oval-shaped hardware accents
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000622
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Mood Set Strapless Ruffled Mini Dress
Soft, sheer, and made for late plans. This strapless mini dress hugs through the bodice and flows into a tiered skirt that moves with you, giving effortless drama for nights out, date plans, and anywhere compliments are guaranteed.
Fit & Features
- Burnout velvet pattern, mesh-lined fabric
- Strapless tube neckline
- Form-hugging bodice
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000884
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: PINK, YELLOW
Available Size: XS, L, M
Product Badge:- Best Seller
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Island Heat Mesh Maxi Dress
Booked, busy, and dressed like it. This tropical floral maxi dress is form-hugging with a high side slit that brings just enough drama for your next getaway or sunset dinner.
Fit & Features
- Tropical floral print, mesh fabric, brushed knit lining
- Strapless tube neckline, non-slip grip lining
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000626
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
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Blush Blossom Halter Mini Dress
A little flirty mini dress, a little romantic, and made for sunny plans. This embroidered floral halter mini dress features a soft A-line shape that skims the body, while the delicate tie front and open back keep the look playful.
Fit & Features
- Embroidered floral woven fabric
- Halter neckline with adjustable tie
- Front tie detail at bust
- A-line silhouette with mini-length hem
- Hidden back zipper closure
- Runs true to size
Style Number/Barcode: 05102-000630
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: SAGE, PINK
Available Size: S, M, L
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Tropic Heat Floral Mini Dress
Serving vacation energy even if you’re not booked yet. This floral mesh dress contours your shape with a plunging neckline and open back that does all the talking.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Plunge halter neckline, tie straps
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000625
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Picture Perfect Floral Corset Skater Dress
Soft florals, a cinched corset, and a skirt made to twirl—this one’s pure heart-eyes. The structured bodice keeps everything snatched while the skater silhouette brings effortless movement for brunch dates, parties, and photo-ready plans.
Fit & Features
- Poplin cotton fabric with a structured feel, floral print, tulle and woven linings
- Square neckline with dainty ruffled trim, thin tank shoulder straps
- Corset-inspired bodice with lace-up front detail, boning inserts
- Back zipper closure
- Drop waist silhouette
- Flared skater silhouette, pleated detailing
- Runs true to size
Style Number/Barcode: 05101-000765
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S
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Bare It Back Knot Detail Mini Dress
Business in the front, drama in the back. This mini dress keeps it sleek with a high neckline and bodycon fit, then flips the script with an open back moment perfect for turning heads.
Fit & Features
- Soft stretch knit fabric
- Mock neckline with cap sleeves
- Twist front knot detail at waist
- Open back cutout design
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000635
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L