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.

  • Fall For Me Ruched Midi Dress

    People will fall for you over and over in this sultry curve hugging ruched midi dress! 

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • All over ruched detailing
    • Mid-length, form-fitting style
    • Knit fabric | Knit lining
    • Plenty of stretch

        Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

        Style Number/Barcode: 05102-0532

        Category Name: Casual Dresses

        Price: $9.97 $35.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Sweet like Candy Ruffle Mini Dress

        You’ll be looking sweet for date night in this fab mini dress! It features spaghetti straps, a wrap-front V neckline, front ruching, and a short, form-hugging fit with an asymmetric ruffled front hem. Style the dress with clear heels and a trendy mini bag.

        Fit & Features

        • Spaghetti straps
        • Wrap-front V neckline
        • Ruched detailing
        • Mini-length, asymmetric ruffled hem
        • Curve-hugging silhouette
        • Crepe fabric, moderate stretch
        • Runs true to size

        Style Number/Barcode: 05102-4088

        Category Name: Casual Dresses

        Price: $9.97 $33.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Snake A Difference Side Tie Mini Dress

        Move over LBD! Work your charm in this fiesty mini dress! 

        Fits & Features

        • Spaghetti Straps
        • Square Neckline 
        • Mini Length Silhouette
        • Drawstring & Ruching At Side Hem
        • Knit Fabric 
        • Curve Hugging Fit I Plenty Of Stretch 
        • Zipper Not Featured

        Style Number/Barcode: 05102-0537

        Category Name: Casual Dresses

        Price: $19.97 $33.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Thinkin' Bout It Floral Cowl Neck Mini Dress

        Thinkin' bout those sunny days out at brunch with the galzzz in a cute mini? Well we have the perf dress, the rest is up to you! Pair with a panama hat and booties for that girl-next-door finish!

        Fit & Features

        • Cowl neckline
        • Spaghetti straps
        • Form fitting silhouette
        • Mini hemline
        • Floral ditsy pattern
        • Nylon | Stretchy

        Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.  

        Style Number/Barcode: 05102-0534

        Category Name: Casual Dresses

        Price: $13.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Scoop Neck Midi Dress

        This must-have midi will give you an endless amount of OOTDs to wear and pair. 

        Fits & Features

        • Spaghetti Straps
        • Scoop Neckline I Square Back
        • Midi Length Silhouette
        • Stretchy, Jersey Knit Fabric I Fully Lined
        • Curve Hugging Fit 
        • Moderate Stretch

        Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

          Style Number/Barcode: 05102-0528

          Category Name: Casual Dresses

          Price: $9.97 $34.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Curve Appeal Crepe Mini Dress

          Showcase your curves in this mini dress that says it all! This must-have piece perfectly pairs with pumps and chunky jewelry accents for a bold statement! 

          Fit & Features 

          • V-Neckline | Spaghetti Straps
          • Vertical Princess Seams 
          • Mini Side Slit
          • Lined Crepe Fabric 
          • Form Hugging Fit 
          • Moderate Stretch 

           

           


          Style Number/Barcode: 05102-0526

          Category Name: Casual Dresses

          Price: $11.97 $29.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Casual Stunner Crepe Mini Dress

          Create a casual stunning look with this adorable crepe mini dress that is perf for every day. It features a sleeveless bodice, spaghetti straps, a square neckline, a cute tie-back detail, and a mini-length, curve-hugging silhouette. Style the dress with the tie in the front for a night out. Complete the outfit with a layered necklace and new mules.

          Fit & Features

          • Spaghetti straps
          • Square neckline
          • Tie-back detail
          • Short, form-hugging fit
          • Crepe fabric
          • Runs true to size

          Style Number/Barcode: 05102-0527

          Category Name: Casual Dresses

          Price: $19.97 $28.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Ships Free
        • Feelin' Slick Satin Puff Sleeve Mini Dress

          ...And lookin' slick! We are lovin' the puff sleeve trend and know you are too. You'll be lookin' oh-so-chic, everyone's going to think you came off the runway! 

          Fits & Features

          • Square Neckline 
          • Sheer Mesh Puff Shoulder Short Sleeves
          • Back Zipper With Hook & Eye Closure
          • Mini Length Silhouette 
          • Satin Fabric 
          • Form Hugging Fit I Moderate Stretch 

          Style Number/Barcode: 05101-0589

          Category Name: Casual Dresses

          Price: $12.97 $32.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Ditsy Floral Daze Mini Dress

          Ditsy florals are the trendy print of the season! This floral printed dress features a sleeveless square neckline with ruffle spaghetti straps, ruched detailing down the side, and a mini-length, curve-hugging silhouette. Pair this adorable dress with some cute strappy sandals for the perf daytime 'fit!

          Fit & Features

          • Ruffle spaghetti straps
          • Square neck and back
          • Ruched side detailing, adjustable drawstring at hem
          • Short, form-hugging fit
          • Ditsy floral print
          • Ribbed knit fabric, plenty of stretch
          • Runs true to size

          Style Number/Barcode: 05102-0524

          Category Name: Casual Dresses

          Price: $9.97 $28.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Mesmerizing Beauty Lace-Up Wrap Dress

          Mesmerize with a wrap dress that showcases your best angles! The dress features a sleeveless scoop neckline, spaghetti straps, a lace-up back, a high slit, and a wrap silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit, Complete look with mules. 

          Fit & Features

          • Sleeveless scoop neckline
          • Spaghetti straps
          • Lace-up back 
          • High slit
          • Wrap silhouette
          • Knit fabric
          • Form hugging fit, moderate stretch, runs true to size

          Style Number/Barcode: 05101-0586

          Category Name: Casual Dresses

          Price: $19.97 $36.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Ships Free
        • Button Down Knit Midi Dress

          For the modest yet trendy babe! This midi is a closet staple, whether it's work wear or a casual date night, just throw on some heels and you are lookin' gooood bb!

          Fit & Features

          • V- neckline | Long sleeves
          • Oil slick buttons down the center
          • Mid-length hemline
          • Ribbed knit material
          • Moderate stretch
          • Form fitting silhouette

          Style Number/Barcode: 06005-0516

          Category Name: Casual Dresses

          Price: $20.97 $52.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • New Love Ditsy Smocked Mini Dress

          Something sweet, something new. Charm them all by slipping into the New Love mini dress! Pair with some sneakers for a girls' day and switch to some heels for date night with the boo! 

          Fits & Features 

          • Adjustable Spaghetti Straps
          • Square Neckline
          • Mini Length Silhouette
          • Woven Fabric I All Over Smocking 
          • Ditsy Floral Print I Tiered Ruffle Design 
          • Form Hugging Fit I Ample Stretch 

          Style Number/Barcode: 05102-0522

          Category Name: Casual Dresses

          Price: $15.97 $39.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Get Groovin' Tie Dye Scoop Neck Mini Dress

          Get to movin' bb girl! This fab and fun mini dress features a splash of tie-dye print and goes perfect with white booties or sneakers!

          Fits & Features

          • Tank Shoulder Straps
          • Scoop Neckline
          • Mini Length Hemline
          • Smooth Brush Knit Fabric | Tie Dye Print
          • Form Hugging Fit | Plenty Of Stretch 

           

          Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

          Style Number/Barcode: 05102-0523

          Category Name: Casual Dresses

          Price: $9.97 $24.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Stunning Beauty Tropical Maxi Dress

          Showcase your stunning beauty in this tropical maxi dress on your next weekend getaway! It features a sleeveless V neckline, spaghetti straps that lead to an open back with a strappy design, a high waist, and a floor-length hem with a relaxed fit. The knit fabric has an all-over palm leaf print to bring the vacay vibes. Complete the look with strappy sandals.

          Fit & Features

          • Sleeveless V neckline
          • Spaghetti straps
          • Open back, strappy design
          • High waist
          • Floor-length hem, relaxed fit
          • Knit fabric, palm leaf print
          • Runs true to size

          Style Number/Barcode: 05102-0525

          Category Name: Casual Dresses

          Price: $9.97 $44.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Take Me Back Tropical Maxi Dress

          Get taken back to that dream vacay with a fab maxi dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a tropical print, an open back, a smocked waist, and a flowy maxi length silhouette. Complete with wedges. 

          Fit & Features

          • Sleeveless V-neckline
          • Adjustable spaghetti straps, cross at back 
          • Tropical print
          • Open back 
          • Smocked waist
          • Maxi length silhouette
          • Relaxed fit, minimal stretch, runs true to size

          Style Number/Barcode: 05101-0572

          Category Name: Casual Dresses

          Price: $6.97 $46.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Sleeveless V Neck Ruffled Floral Mini Dress

          Get frilly in a ruffled floral dress. Celebrate with your squad in a floral mini dress that features a sleeveless bodice, a plunging V neckline, and spaghetti straps. The relaxed fit waist leads to a mini-length silhouette with a frilly ruffled hem. The all-over floral print features bright hues that contrast with the dark background. Complete your look with wedges and sunglasses.

          Fit & Features

          • Sleeveless V neckline
          • Spaghetti straps
          • Floral print 
          • Mini-length silhouette
          • Ruffled hem
          • Lightweight knit fabric with a moderate stretch
          • Runs true to size

          Style Number/Barcode: 05102-0517

          Category Name: Casual Dresses

          Price: $6.97 $26.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Ships Free
        • Flirty In Florals Midi Dress

          Get a little flirty in pretty florals with this gorg printed midi dress!

          Fit & Features

          • Adjustable spaghetti straps | Cross back
          • V neckline
          • Ruched side detailing
          • Asymmetric hem
          • Mid-length, curve hugging fit
          • All over floral print
          • Knit fabric | Plenty of stretch

          Model is 5'9" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

          Style Number/Barcode: 05102-0516

          Category Name: Casual Dresses

          Price: $9.97 $34.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Falling For It Ruffled Chiffon Leopard Print Dress

          Have them all falling for you when you step out in this flirty chiffon ruffled mini dress! Easily style with a pair of black mules and sweet pearl hoops!

          Fit & Features

          • Ruffle trim mock neckline
          • Long sleeves with a ruffled wrist
          • Relaxed bodice
          • Stretchy smocked waist line
          • Tired ruffled skirt
          • Mini hemline | Lined at the skirt
          • Slip on fit | No closures

          Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

          Style Number/Barcode: 05102-0513

          Category Name: Casual Dresses

          Price: $9.97 $42.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Puff Sleeve Leopard Print Mini Dress

          Puff sleeves and leopard print - this mini dress couldn't get any trendier!

          Fit & Features

          • Off the shoulder neckline
          • Short puff sleeves
          • High waist seam
          • Short, form hugging fit
          • Leopard print
          • Knit fabric | Plenty of stretch
          • Form hugging fit

          Style Number/Barcode: 05102-0521

          Category Name: Casual Dresses

          Price: $9.97 $30.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Go Get 'Em Tiger Print Cowl Neck Mini Dress

          Girl, go get em' in tiger print! We will always love our classic leopard print but have been gradually leaning into tiger to change it up and stand out a lil'! Pair with a leather jacket and boots, or black heels!

          Fit & Features

          • Cowl neckline
          • Spaghetti straps that cross in the back
          • Mini hemline
          • Form fitting silhouette
          • Side slit detail
          • Lined at the bust | Lots of stretch
          • Tiger print pattern

          Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small. 

          Style Number/Barcode: 05102-0518

          Category Name: Casual Dresses

          Price: $11.97 $29.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Can't Forget Me Floral Side Ruched Mini Dress

          Honey, they can't even take their eyes off of you! Walk around like the goddess you are in this figure-hugging mini dress! Don't forget to add some heels to really pull th look together for that brunch you got planned 

          Fits & Features

          • Adjustable Spaghetti Straps 
          • V Neckline I Square Back 
          • Mini Length Silhouette 
          • Ruching Along Side Seam 
          • Stretchy Woven Fabric 
          • Form Hugging Fit I Plenty Of Stretch 

          Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

          Style Number/Barcode: 05102-0520

          Category Name: Casual Dresses

          Price: $9.97 $34.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Flowy In Floral Tie Waist Mini Dress

          Charm them all with this pretty mini dress! It's perf for those upcoming warm and sunny days. 

          Fits & Features

          • Adjustable Spaghetti Straps 
          • V Neckline I Smocked Back 
          • Waist Tie Design
          • Mini Length Silhouette I Wrap Skirt Design
          • Crinkle, Gauze Lined Fabric I Floral Prints 
          • Moderate Stretch 

          Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

          Style Number/Barcode: 05102-0514

          Category Name: Casual Dresses

          Price: $9.97 $42.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Angora Knit Leopard Print Sweater Dress

          Cozy and chic, this leopard print sweater dress is purrfect for the season.

          Fit & Features

          • Turtleneck
          • Long sleeves
          • Ribbed hems
          • Leopard print
          • Angora fuzzy knit fabric | Moderate stretch
          • Relaxed, comfortable fit

          Style Number/Barcode: 06005-0507

          Category Name: Casual Dresses

          Price: $4.97 $39.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Floral Bliss Smocked Mini Dress

          Bring out the floral prints and wave those gloomy winter-blues goodbye! Radiate that early springtime energy in this cute mini dress! 

          Fits & Features 

          • Adjustable Spaghetti Straps 
          • Lettuce Edge Trim At Square Neckline & Hem 
          • Smocking Throughout 
          • Mini Length Silhouette 
          • Curve Hugging Fit 
          • Ample Stretch 

          Style Number/Barcode: 05102-0519

          Category Name: Casual Dresses

          Price: $19.97 $34.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale