Casual Dresses

Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • Trendy Neutral Tie-Dye Mini Dress

    This trendy neutral tie-dye mini dress will step up your casual summer looks. It features a sleeveless scoop neckline, dual spaghetti straps that lead to a cross-back, strappy design, and a short, curve-hugging, bodycon silhouette. The brushed knit fabric offers plenty of stretch. Style with chic mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Dual spaghetti straps
    • Cross-back strap design, lower back bar straps
    • Mini-length, form-fitting, bodycon silhouette
    • Tie-dye print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4690

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boogie On Down Lace-Up Mini Dress

    Boogie all over town in this retro mini dress featuring a sleeveless, square neck, spaghetti straps, a trendy lace-up on the back, bodycon silhouette, on swirl marble print knit fabric with a moderate stretch. Complete your groovy fit with strappy stiletto heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Mini-length hem
    • Swirl marble print
    • Knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4688

    Category Name: Casual Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Summer Mood Knit Mini Dress

    This stretchy ribbed knit mini dress is perfect for those casual summer days. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing down the side seams with adjustable drawstrings at the hem, and a short, curve-hugging silhouette. Style with cute slides.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Ruching down the side seams, adjustable drawstrings at the hem
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4685

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Me On A Getaway Midi Dress

    You'll be ready for a fab weekend getaway in this curve-hugging midi dress! It features a sleeveless sweetheart neckline with halter straps, chic waist cutouts, and a midi-length, form-fitting silhouette with a thigh-high side slit. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Waist cutouts
    • Midi-length, form-fitting silhouette, high side slit
    • Textured ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4687

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eyes For One Shoulder Sweater Dress

    Everyone will only have eyes for you in this one-shoulder sweater dress featuring a long sleeve, flirty choker neck, a side waist cutout, and a form-hugging midi hem with a slit. Pair with strappy stiletto heels to complete the look!

    Fit & Features

    • One-shoulder, long sleeve
    • Choker neck
    • Side waist cutout
    • Form-hugging silhouette
    • Slit midi-length hem
    • Soft sweater-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1495

    Category Name: Casual Dresses

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Glam Ruched Short Dress

    Keep it glam on your tropical getaway with a mini dress that brings those island vibes! The dress features a tropical floral print, a sleeveless square neckline, spaghetti straps, ruching, and a short length with a rounded hem. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a straw hat. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching
    • Tropical floral print
    • Short length hem
    • Lined smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4683

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Away On Vacay Tropical Mini Dress

    Going away on vacation? This tropical mini dress will definitely get you in the vacay mood! It features a sleeveless, scoop neck, spaghetti straps, a form-hugging silhouette, and a side ruched seam that leads to the asymmetrical slit hem. Complete the look in chic oversized sunnies.

    Fit & Features

    • Sleeveless, scoop neck
    • Spaghetti straps
    • Form-hugging silhouette
    • Side ruched seam, asymmetrical slit hem
    • Mini-length 
    • Tropical print, sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4682

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Note V-Neck Sweater Dress

    Everyone will take note of how sultry this sweater dress is on you! It features a sleeveless, v-neck, cutout bodice with wrap tie-back closure, side slit accent, and a midi, curve-hugging silhouette. Complete the look in chic strappy heels for a daytime soiree.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, v-neck, tank-style straps
    • Cutout bodice
    • Wrap tie-back closure
    • Side slit accent
    • Midi, curve-hugging silhouette
    • Sweater rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1488

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Catch Up Crepe Slip Midi Dress

    This sleek slip midi dress is perfect for bringing chic vibes when catching up with friends! It features a sleeveless V-neck bodice with bungee spaghetti straps, a form-fitting silhouette to show off your figure, and a sultry front slit on the mid-length hem. The crepe fabric offers a moderate stretch. Complete your look with classic block heels.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Form-fitting silhouette
    • Front slit, midi-length hem
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5400

    Category Name: Casual Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Only View One Shoulder Sweater Dress

    You're the best view around in this one-shoulder dress! It features a sleeveless bodice, a single strap, cutouts along the waist, a bodycon silhouette, and a side slit midi hem. Complete the look in hoop earrings and heels.

    Fit & Features

    • Sleeveless, one-shoulder, single strap
    • Cutouts along the waist
    • Side slit
    • Bodycon silhouette
    • Midi hem 
    • Sweater rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1489

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blooming Beauty Floral Midi Dress

    Bloom with beauty in this gorgeous floral midi dress perfect for the season! It features a sleeveless square neckline, spaghetti straps, a knot-front design at the waist with ruching, a midi-length hem with a chic high front slit, and a curve-hugging fit. The stretchy knit fabric showcases a stunning bold floral print. Style with platform heels for a bridal shower.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, square back
    • High waist seam, knot-front design, ruching
    • Midi-length hem, high front slit
    • Form-hugging fit
    • Bold floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1678

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Resort Ready Palm Print Mini Dress

    You'll be ready for your getaway at the resort with this tropical mini dress in your arsenal! It features a sleeveless square neck, sleek spaghetti straps, a palm print, and a curve-hugging silhouette. Complete your vacay look in espadrille wedges.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Curve-hugging silhouette
    • Mini-length hem
    • Palm print
    • Soft brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4681

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Trendy Fave Mesh Mini Dress

    This adorable mini dress will be a new trendy fave! It features a sleeveless square neckline, bungee spaghetti straps, ruching down the side seams, and a short, curve-hugging, bodycon silhouette. The lined mesh fabric features an all-over tie-dye print pattern. Complete the look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting, bodycon silhouette
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4679

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall Nights Satin Button-Up Short Dress

    The perfect satin short dress for a night of wine and dining! Featuring long sleeves with buttoned cuffs, a collar neckline, button-up front closures, a smocked waist, and a curved short-length hem. Complete the look in knee-high boots.

    Fit & Features

    • Long sleeves, buttoned cuffs
    • Collar neckline
    • Button-up front closures
    • Smocked waist
    • Curved short-length hem
    • Smooth satin fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1927

    Category Name: Casual Dresses

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Treat Puff Sleeve Mini Dress

    This puff sleeve mini dress is the perfect sunny day sweet treat! It features a scoop neck, empire waist seam, bodycon silhouette, and a mini-length hem on jersey knit-lined fabric with a moderate stretch. Complete the look with a chic crossbody bag for a day out.

    Fit & Features

    • Puff sleeves
    • Scoop neck
    • Empire waist seam
    • Bodycon silhouette
    • Mini-length hem
    • Jersey knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4677

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Summer Style Knit Midi Dress

    Showcase that effortless summer style this season with this ribbed knit midi dress. It features a sleeveless one-shoulder neckline with a single spaghetti strap, a ruched side cutout with an adjustable drawstring, and a midi-length, curve-hugging silhouette with a chic front slit. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless one-shoulder neckline, single spaghetti strap
    • Ruched side cutout, adjustable drawstring
    • Form-fitting silhouette, front slit
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4674

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sandy Toes Crochet Bodysuit Dress

    The perfect long dress to walk the sandy beaches! This crochet maxi features a sleeveless, V-neck, adjustable spaghetti straps, dual front hoop inserts, and a bodysuit lining with dual-snap button closure on a cheeky bottom. Complete the look in boho earrings and a bracelet.

    Fit & Features

    • Sleeveless, V-neck, adjustable spaghetti straps
    • Dual front hoop inserts
    • Bodysuit lining, dual snap-button closure, cheeky bottom
    • Form-fitting silhouette
    • Maxi-length hem
    • Sheer crochet fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4675

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good For You Sweater Maxi Dress

    Cause you like looking good for yourself! This sweater maxi dress is the perfect staple for your seasonal closet. It features long sleeves, a collared v-neckline, a form-hugging silhouette, and a flirty front cutout slit. Style with booties for an afternoon lunch.

    Fit & Features

    • Long sleeves
    • Collared v-neckline
    • Form-hugging silhouette
    • Front cutout slit
    • Maxi-length hem
    • Ribbed knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1482

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Refresh Striped Sweater Dress

    Refresh your closet in this striped sweater dress featuring a sleeveless, crew neckline, bodycon silhouette, and a mini-length hem on stretchy, rib-knit fabric. Complete your trendy look in statement heels.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, crew neckline
    • Bodycon silhouette
    • Mini-length hem
    • Striped pattern
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1485

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Brush With Fate Halter Mini Dress

    Fate must've brought you and this halter mini dress together! It features a sleeveless, plunge V-neckline, tie-back neck closure, and a center front hoop insert atop the form-fitting silhouette. Complete the look in simple block heels for a sultry vibe.

    Fit & Features

    • Sleeveless, plunge halter V-neck, tie-back neck closure
    • Center front hoop insert
    • Form-fitting silhouette
    • Mini-length hem
    • Rib-knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4669

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twirl All Day Linen Skater Dress

    You'll be twirling all day in this linen skater dress perfect for a day date or Sunday brunch! It features a sleeveless, square neck, adjustable spaghetti straps, fitted bust, open-back with an elasticized band, and a flowy short hem. Complete the look in PVC strap heels.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Fitted bust
    • Open-back, elasticized band
    • Flowy skater silhouette
    • Short length hem
    • Linen woven fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1667

    Category Name: Casual Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Staple Bodycon Mini Dress

    This chic mini dress is an elevated staple! It features a sleeveless mock neckline, tank shoulder straps, and a mini-length, form-hugging, bodycon silhouette. Style with strappy mules and a cute handbag.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Mini-length hem
    • Bodycon silhouette
    • Brushed knit fabric, knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4663

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever In Floral Mini Dress

    They can catch you forever in this floral mini dress! It features a sleeveless sweetheart neckline, spaghetti straps, and a tie-front along the bust on ribbed knit fabric that offers a form-hugging fit. Complete the look in flirty mules for a daytime occasion.

    Fit & Features

    • Sleeveless, sweetheart neck, spaghetti straps
    • Tie-front along the bust
    • Form-hugging fit
    • Mini-length hem
    • Ditsy floral print
    • Ribbed-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4668

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Muse Satin Slip Dress

    You'll be a total retro muse in this sleek satin slip dress! It features a sleeveless V-neckline with a tie-front bodice, adjustable spaghetti straps, a short, A-line silhouette, and an all-over multi-colored swirl print pattern. Style this dress with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless V-neckline, tie-front detail, small cutout
    • Adjustable spaghetti straps
    • Mini-length, A-line silhouette
    • All-over multi-colored swirl print
    • Woven satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4665

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale