Casual Dresses

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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!

  • Pretty In Motion Halter Mini Dress

    Caught a vibe and dressed for it. This halter mini dress cinches at the waist with a flowy A-line skirt that moves with you—perfect for weekends that start with plans and end wherever.

    Fit & Features

    • Smooth stretch material
    • Halter neckline with open back, tie straps
    • Ruched waist detail
    • A-line mini silhouette with pleated skirt
    • Runs true to size

    Style Number/Barcode: 05102-000358

    Category Name: Casual Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: ROYAL

    Available Size: XS, S, M, L

  • Coastal Crush Cutout Crochet Maxi Dress

    A dress that does the flirting for you. The cutout crochet shows just enough, while the shell and sequin details add that subtle shimmer that catches light—and attention—without trying. This is your out-all-day, glow-all-night kind of maxi dress.

    Fit & Features

    • Sheer crochet knit fabric, mini-length knit lining, moderate stretch
    • Sleeveless ruched knit top, no-slip strip, wired V-neckline
    • Tie-back halter spaghetti straps, eyelet trim, shell and sequin embellishments
    • Partially open back
    • Maxi-length hem, high-cut side slit
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000360

    Category Name: Casual Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Sweet Trouble Halter Romper

    Playful yet bold. This halter plunge romper stuns with cascading ruffles and a flirty fit that’s ready for parties or date nights.

    Fit & Features

    • Smooth knit-lined stretchy fabric
    • Plunge halter neckline, tie closure
    • Side ruched seams
    • Ruffled layer mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000192

    Category Name: Casual Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

  • Sleek Attitude Cutout Mini Tube Dress

    Sleek with a hint of attitude—this cutout tube dress leans into confidence without overdoing it. The smooth knit hugs effortlessly, while the cutout crisscross beading gives your waist that sculpted, stop-scrolling energy.

    Fit & Features

    • Smooth double-lined knit fabric, high stretch
    • Strapless straight-across neckline
    • Front waist cutout
    • Asymmetric strappy design, beaded stone accents
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000359

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Yours Floral Romper

    Steal the scene in this romantic flocked floral romper featuring a sultry halter neckline and flirty ruffled hem. The open strappy back adds just the right amount of drama for your weekend plans.

    Fit & Features

    • Flocked velvet floral pattern, mesh-lined fabric
    • Plunge cowl halter neckline, tie closure
    • Open dual tie-back design
    • Form-hugging bodice
    • Ruffled mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000193

    Category Name: Casual Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winter Crush Sherpa Trim Faux Leather Tube Dress

    Think après-ski, but make it going-out glam. The faux leather gives you that sleek, sculpted confidence, while the faux sherpa trim adds that touch of softness that balances the boldness just right. It’s the kind of piece that feels luxe, a little daring, and completely worth showing off.

    Fit & Features

    • Faux leather fabric with sewn-in knit lining, moderate stretch
    • Faux sherpa trims
    • Strapless straight-across neckline, no-slip strip
    • Back zipper with hook-eye closure
    • Dual belted accents at the waist
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000362

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Off-The-Shoulder Mini Dress

    This long sleeve off-the-shoulder mini dress hugs in all the right places for that effortless “oh, this old thing?” vibe. Perfect for brunch, dinner dates, or any casual night out plans.

    Fit & Features

    • Smooth knit-lined stretchy fabric
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves with flare slit cuffs
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000363

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Whispers Ruffle Mini Dress

    Bring the drama (and the movement). This strapless mesh mini features a sweetheart neckline with a sultry O-ring cutout, open tie-back design, and layered ruffle skirt made to turn heads on every dance floor.

    Fit & Features

    • Abstract print mesh-lined stretch fabric
    • Strapless sweetheart neckline
    • Hoop insert, padded bra cups
    • Strappy open tie-back
    • Ruched bodycon fit
    • Tiered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000367

    Category Name: Casual Dresses

    Price: $18.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prep School Princess Rhinestone Collar Shirt Dress

    This polished poplin mini dress gets a glam upgrade with a gorge rhinestone-encrusted collar that instantly elevates your whole vibe. The corset-inspired seaming snatches your waist just right, while the flared skirt keeps things flirty. Whether you’re styling it with sheer tights and heels or chunky boots and a shoulder bag, this dress delivers classy-with-a-twist energy every single time.

    Fit & Features

    • Woven cotton-blend poplin fabric with structured hand
    • Pointed collar adorned with rhinestone embellishments
    • Long sleeves with buttoned cuffs
    • Fitted corset-style waist with front pleating
    • Mini-length button-up silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000366

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wildly Fierce Leopard Floral Maxi Dress

    Warning: this dress doesn’t do low profile. The leopard floral mesh print fabric and plunge halter neckline with bead inset sculpt a form-hugging maxi silhouette that’s made for vacations, birthday dinners, and any plan that deserves a little drama.

    Fit & Features

    • Floral, leopard print mesh-lined fabric
    • Plunge halter neckline with tie and bead
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000365

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Barefoot Glam Sequin Mini Dress

    This is the dress that makes every plan feel like a getaway. With its shimmering payette sequin texture and open-back detail, it’s made for sunny getaways, destination dinners, and dancing after sunset.

    Fit & Features

    • Allover payette sequin embellishment, knit lining
    • Spaghetti straps 
    • V-neckline
    • Sleeveless bodice with a fitted silhouette
    • Open back with adjustable lace-up tie detail
    • Mini-length hem with dangling shell trim
    • Runs true to size

    Style Number/Barcode: 05103-000842

    Category Name: Casual Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: IVORY-2

    Available Size: XS, S, M, L

  • Worth The Wait Chain Detail Maxi Dress

    The kind of dress that changes the whole plan. This abstract print maxi dress combines a plunging cowl neckline, draped chain detail, and an open-back silhouette for a look that's both art exhibit and dinner reservation.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Abstract print
    • Sleeveless plunging cowl neckline, triple chain strap accents
    • Tie-back halter straps, open back
    • Maxi-length hem, high-cut back slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000370

    Category Name: Casual Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: PLUM

    Available Size: XS, S, M, L

  • Polished Curves Off-Shoulder Knit Midi Dress

    This midi dress keeps it classy with a side of allure—the foldover neckline, sleek rib knit, and gold hardware detail turn a timeless silhouette into a subtle showstopper. It’s the kind of dress that makes minimal feel magnetic.

    Fit & Features

    • Rib knit fabric
    • Foldover off-shoulder neckline with hardware accent
    • Long fitted sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000232

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrapped in Charm Rib Knit Dress

    Soft meets sultry in this rib knit mini dress made for showing a little shoulder. The foldover neckline, waist wrap belt, and ruffled hem bring that flirty-feminine vibe—perfect for when cozy still calls for a look.

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Wrap waist belt accent with hardware insert
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000371

    Category Name: Casual Dresses

    Price: $30.00 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S

    Product Badge:
    • Sale
  • In Your Element Off-Shoulder Mesh Twist Midi Dress

    This midi knows how to move—soft mesh, abstract swirls, and an off-shoulder twist that feels effortlessly seductive. The high side slit adds that perfect hint of drama, making every step a little more intentional.

    Fit & Features

    • Abstract printed mesh fabric, knit lining
    • Off-shoulder neckline with twist detail
    • Bodycon silhouette
    • High side slit for ease of movement
    • Runs true to size

    Style Number/Barcode: 05102-000372

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Quietly Bold Lattice Side Midi Dress

    This is the kind of dress that holds eye contact a second longer. Clean lines up front with a subtle lattice moment down the side make it feel polished, confident, and a little unexpected.

    Fit & Features

    • Ribbed knit fabric with stretch
    • Square neckline
    • Fitted long sleeves
    • Side lattice cutout detailing
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000233

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Untamed Rhythm Halter Mini Dress

    Made for movement and meant to turn heads. This abstract mesh halter mini dress features a soft cowl neckline, open back, and flirty tiered ruffle hem that dances with every step.

    Fit & Features

    • Abstract print, mesh-lined stretch fabric
    • Cowl halter neckline with tie closure
    • Open back
    • Form-hugging fit
    • Tiered ruffle mini hem
    • Runs true to size

    Style Number/Barcode: 05102-000373

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Intentions Zebra Velvet Maxi Dress

    A little wild, a lot unforgettable. This burnout zebra velvet mesh maxi brings high-drama energy with its one-shoulder neckline, side cutout, and ruched bungee drawstring that lets you play with the slit height. Equal parts sleek and scandalous—just how we like it.

    Fit & Features

    • Zebra burnout velvet pattern, mesh fabric, sewn-in mesh lining
    • One-shoulder neckline, bungee spaghetti strap
    • Strappy back, bodice side cutout
    • High front slit and ruched drawstring bungee cord
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000757

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Vibes Geometric Knit Halter Mini Dress

    Meet the mini dress that knows how to make an entrance without trying too hard. The geometric knit hugs just right, giving you that effortless, sculpted look for beach nights, rooftop drinks, and the best vacay vibes.

    Fit & Features

    • Sheer embroidered knit fabric, knit lining, high stretch
    • Abstract geometric pattern, metallic woven threading
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000377

    Category Name: Casual Dresses

    Price: $45.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

  • Luxe Moments Removable Faux Fur Mini Dress

    Giving retro glam with a cozy twist, this ribbed mini dress brings major soft-lux vibes. The faux fur collar and cuffs add effortless drama, making it the perfect piece for chilly nights when you still want to look very put together.

    Fit & Features

    • Rib knit fabric
    • Deep V neckline with a removable faux fur collar
    • Long sleeves with removable faux fur cuffs
    • Front button-down design for adjustable coverage
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000378

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back To Bold Mock Neck Mini Dress

    Minimal from the front, major from the back. This mini dress offers a bold cutout back with hoop accents and a bodycon fit that turns heads and gives your rotation a trendy upgrade. 

    Fit & Features

    • Ribbed knit fabric with stretch
    • Mock neckline with fitted long sleeves
    • Sleek bodycon silhouette through the bodice
    • Open-back cutout detail with a detachable hoop chain accent
    • Mini-length skirt with a front side slit
    • Runs true to size

    Style Number/Barcode: 06005-000261

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch Crush Eyelet Skater Dress

    Caught feelings for this one instantly. This eyelet knit skater dress hugs through the bodice, then flares into the prettiest mini, made for brunch dates, grad pics, and those “just stepped out” kind of days.

    Fit & Features

    • Eyelet knit fabric with knit lining, moderate stretch
    • Sleeveless square neckline
    • Princess seams
    • Adjustable spaghetti straps
    • Mini-length hem
    • Skater silhouette, godet detailing
    • Runs true to size

    Style Number/Barcode: 05102-000381

    Category Name: Casual Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale