Workwear Dresses

Elevate your professional wardrobe with our sophisticated collection of work dresses, perfect for speaking presentations to business casual days. Our selection is tailored to meet the demands of the modern workplace, ensuring you find the ideal dress to showcase your style and professionalism. Opt for a refined crepe midi dress that exudes elegance and grace, ideal for important meetings or a day at the office. For a more contemporary twist, explore our sweater dresses, blending classic style with modern comfort. Whether you're presenting in the boardroom or networking at a business luncheon, our work dresses are designed to make a statement, balancing the perfect blend of sophistication, functionality, and style

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WORKWEAR DRESSES
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Fall Workwear Dresses for the Office, Conference, or Meeting

Refresh your fall wardrobe with our latest workwear dresses, designed to elevate your professional style while keeping you cozy as the temperatures drop. Perfect for office days, industry conferences, or after-hours events, our work dresses combine style, comfort, and versatility to ensure you're ready for anything the day brings.

This season, embrace the chic 2024 trends with midi dresses in ribbed sweater knit and woven crepe—ideal for creating an elegant, tailored look. These midi styles not only elongate your silhouette but also provide a polished below-the-knee length that’s perfect for your workday. Pair a sleeveless midi dress with a tailored blazer and classic point-toe heels for a sharp, professional ensemble.

As fall settles in, layer up with a cozy cardigan over a dark floral or abstract print dress and finish the look with tall boots for a stylish boho-inspired outfit. For a business casual vibe, consider a ribbed knit midi dress teamed with a denim jacket and ankle booties, striking the perfect balance between comfort and polish. These midi-length work dresses from Windsor are a must-have for easy, everyday styling.

Knit and sweater dresses are your go-to choices for both the nine-to-five grind and any work-related events. These all-in-one ensembles are versatile enough to transition from day to night—just swap your blazer for a faux leather moto jacket before heading to happy hour or a client dinner.

Prepare to make power moves this fall with our collection of workwear dresses that will keep you looking effortlessly chic and professional. Explore our latest arrivals now and start curating your perfect 2024 fall work wardrobe. Shop online or visit your nearest Windsor store today!

How can I style a dress for work?

You can style your work dresses with layers, statement and minimal jewelry, and chic footwear. Starting with layers, you can layer your workwear dress with structured or boyfriend blazers to elevate your business casual look. You can style your blazer by rolling the sleeves up to a quarter length, then adorn your look with dainty chain link bracelets. For your sleeveless dresses that may not be work-appropriate when worn alone, you can style these dresses with long sleeve tops or collared blouses underneath to refresh your sleeveless dresses for work. Another chic layering option could be styling your tie-front tops over your sleeveless or strapless dresses. Be sure to choose a pattern that compliments your dress. Avoid clashing by pairing prints with muted colors to create a seamless contrast that goes together. Be sure to add accessories like statement necklaces, dainty chain-link necklaces, versatile hoops, and studs that elevate your workwear outfits. For your footwear, you can style your dress with sturdy mules, block heels, or ankle booties that are comfortable enough to wear all day but give your dresses a stylish feel—avoid wedges and sandals that may be deemed too casual for the workplace.

How do I know if my dress is ok to wear at work?

The best way to know if your dress is ok to wear at work is to consult your employee handbook to gauge whether your outfit is in line with the dress code. Now if your handbook isn’t explicitly clear on the dress code, a good rule of thumb would be to dress business casual or err on the side of classic and accessible. For the fabrication choose dresses that come in durable fabrications like ribbed knit, Ponte knit, and crepe—avoid sheer fabrics that can reveal more than you’d like to at work. For example, it’s best to not have any spaghetti straps, strapless styles, or halter dresses without another layer. That’s where sweaters and blazers as layering pieces come in handy to make sure your dress is work-appropriate. In addition, you should also think about the length of your dress and how tight it is. If it seems more club-appropriate than work-appropriate, it’s best to leave it at home and reach for a classic shift dress instead. The bottom line is that you want to look professional in all that you do in your career or that part-time gig, and wearing a work-appropriate dress sends just that message.

  • Casual Chic Ruched Ribbed Knit Maxi Dress

    Effortlessly elevate your everyday looks with this casual chic ribbed knit maxi dress. It features a sleeveless boat neckline, tank shoulder straps with a trendy twist-back design, ruched side seams at the waist to accentuate your curves, and a fitted A-line silhouette with a maxi-length hem to flaunt your figure. Style with hoop earrings and strappy mules.

    Fit & Features

    • Stretchy ribbed knit
    • Boat neckline
    • Tank shoulder straps, twist-back design
    • Side ruching at the waist
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5834

    Category Name: Workwear Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: GRAY, BLACK

    Available Size: S, M, L

  • Compliment Me High Slit Knit Midi Dress

    You'll spark up all the compliments in this simply chic high slit midi dress! Designed with a stretchy structured knit fabric, this dress is shaped with a sleeveless square neck and back with thin tank shoulder straps. The mid-length hem is accented with a high-cut side slit to show off some leg, and the bodycon silhouette will flaunt your stunning curves. Style with a faux leather jacket and heels to go bar-hopping!

    Fit & Features

    • Stretchy structured knit fabric
    • Sleeveless square neck and back
    • Tank shoulder straps
    • High side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5526

    Category Name: Workwear Dresses

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy-Chic Belted And Pleated Skater Dress

    This preppy-chic twill skater dress features a collared neckline with a partial button-down front, short cap sleeves, and a subtle drop waist with a belted design. The mini-length pleated skater fit adds that flirty touch to the short silhouette.

    Fit & Features

    • Twill woven fabric
    • Collared neckline, button-down front
    • Cap sleeves
    • Belted drop waist
    • Mini-length pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5915

    Category Name: Workwear Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Living A Dream Marble Off-The-Shoulder Midi Dress

    This dreamy mesh midi dress is ready for you to take on any event! The stylish marble mesh fabric is sure to make a dramatic statement with its off-the-shoulder neckline, ruched fitted sheer long sleeves, flattering side ruched seams, and bodycon silhouette. Complete the look in stiletto heels for a birthday dinner or date night!

    Fit & Features

    • Off-the-shoulder neckline
    • Ruched fitted sheer long sleeves
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Marble print, mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5332

    Category Name: Workwear Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Check It Plaid Mini Skirt With Suspenders

    Check this plaid mini skirt into your weekly lineup! Featuring a mid-rise waist with suspender straps with tie closure, a bodycon silhouette, and a flirty slit along the hem. Style with a basic tee and boots for a cute complete look!

    Fit & Features

    • Mid-rise waist
    • Suspender straps with tie closure
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Plaid pattern, texture knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06501-0970

    Category Name: Workwear Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Looks Mock Neck Long Sleeve Knit Midi Dress

    This mock neck midi dress will look so good on you! The midi dress features fitted long sleeves, a flattering form-hugging fit, and a center back slit on soft and stretchy ribbed knit fabric. Complete the look with a moto jacket for day or evening plans!

    Fit & Features

    • Soft and stretchy ribbed knit fabric
    • Mock neckline
    • Fitted long sleeves
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5221

    Category Name: Workwear Dresses

    Price: $26.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS, S, M, L

  • Resort Babe Distressed Sweater Mini Dress

    A chic sweater mini dress that'll have you dreaming of your next getaway plans or sunny adventure! The mini-length dress is designed with fitted long sleeves, a crew neckline, a flattering bodycon silhouette, trendy side cutout accents to show a peak of skin and an asymmetrical hem on distressed soft sweater knit fabric. Complete the look in clear sandals and a handbag!

    Fit & Features

    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Side cutout accents
    • Asymmetrical mini-length hem
    • Distressed soft sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1837

    Category Name: Workwear Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Things To Do Ponte Plaid Blazer Dress

    You've got things to do and this ponte plaid blazer mini dress will keep you chic throughout the day! Designed with a trendy glen plaid print, this mini blazer dress features long sleeves, a lapel collar neckline, double-breasted button closures, faux pockets, and a form-hugging fit. Complete the look in knee-high boots and a purse!

    Fit & Features

    • Long sleeves
    • Lapel collar neckline
    • Double-breasted button closures
    • Form-hugging fit
    • Mini-length hem
    • Glen plaid print, ponte fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06204-1684

    Category Name: Workwear Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely In Lace Ruffled Puff Sleeve Mini Dress

    You'll be looking oh-so-lovely in this adorable ruffled puff sleeve mini dress! The sheer floral lace fabric gives that dainty-chic vibe, while the partial knit lining provides coverage. The mini-length dress features a square neckline and sheer short puff sleeves with the cutest ruffle trim, a small bust cutout with a sleek ribbon tie-front design, and a flattering empire waist seam. The flowy A-line silhouette adds that effortless flair. Style this short dress with heeled mules for date night.

    Fit & Features

    • Sheer floral lace fabric with knit lining, minimal stretch
    • Square neckline, ruffle trim
    • Sheer short puff sleeves, ruffle trim
    • Bust cutout, tie-front design
    • Empire waist seam, hidden side zipper closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3338

    Category Name: Workwear Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Highly Selective Choker Neck Sweater Midi Dress

    Highly sophisticated and selective, this off-the-shoulder sweater midi dress is an exquisite piece for any occasion! It features a choker neckline, fitted long sleeves, and a bodycon and midi-length hem to ensure you look polished and elegant. Complete the look in booties for dinner and drinks!

    Fit & Features

    • Off-the-shoulder, choker neckline
    • Fitted long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Sweater ribbed knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1897

    Category Name: Workwear Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple Staple Ribbed Knit Bodycon Mini Dress

    Comfy and chic, this knit bodycon mini dress is the simple staple you need in your closet! Made with a stretchy ribbed knit fabric, it features a sleeveless scoop neckline, spaghetti straps, and a form-hugging fit to flaunt your curves along the bodycon silhouette. Style this mini-length dress with a denim jacket and sneakers for a cute and casual vibe.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Scoop neckline
    • Spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1937

    Category Name: Workwear Dresses

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK, TAUPE

    Available Size: S, M, L, XS

  • Total Feels Sleeveless Maxi Sweater Dress

    You'll love how you feel in this sleeveless maxi sweater dress perfect for casual day-to-night occasions! The maxi-length dress features a mock neckline, a form-hugging fit, and a flirty high slit along the hem. Complete the look in booties.

    Fit & Features

    • Sleeveless mock neck
    • Form-hugging fit
    • High slit
    • Maxi-length hem
    • Sweater ribbed knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1900

    Category Name: Workwear Dresses

    Price: $3.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Beauty Chiffon A-Line Midi Dress

    Create a truly beautiful look for spring and summer weddings in this floral chiffon midi dress! The airy chiffon fabric showcases a blooming floral print and includes a stretchy knit lining for coverage. The tea-length dress is shaped with a sleeveless square neckline and adjustable spaghetti straps for a perfect customized fit. Smocking at the back provides added stretch and features a secure zipper closure. The fitted high waist seam flows out to a classic A-line silhouette with a front slit for extra movement. Style this pretty midi dress with sleek hoops and block heels.

    Fit & Features

    • Sheer chiffon fabric with stretchy knit lining, floral print
    • Sleeveless square neckline, no-slip strip, adjustable spaghetti straps
    • Stretchy smocked back, zipper with hook and eye closure
    • High waist seam, front slit
    • A-line silhouette
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05101-2356

    Category Name: Workwear Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Match Sleeveless Striped Ribbed Knit Mini Dress

    You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

    Fit & Features

    • Striped pattern
    • Ribbed knit fabric with moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Cutout back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1940

    Category Name: Workwear Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: TAN

    Available Size: S, M

  • Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress

    Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Twisted bust, cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5280

    Category Name: Workwear Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS

  • Find Your Style Button Down Pleated Mini Dress

    Make a style statement in this woven shirt mini dress! Featuring long sleeves with button cuffs, a collar neckline, a button down front, and a flattering A-line silhouette and pleated mini-length hem for an adorable and undeniable stylish look. Complete the look in knee-high boots for brunch downtown!

    Fit & Features

    • Long sleeves with button cuffs
    • Collar neckline
    • Button down front
    • A-line silhouette
    • Pleated mini-length hem
    • Woven poplin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5379

    Category Name: Workwear Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

  • Showstoppin' Staple Long Sleeve Maxi Dress

    Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!

    Fit & Features

    • Hacci rib knit fabric, plenty of stretch
    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5887

    Category Name: Workwear Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L, XL

  • Glimmer Girl Long Sleeve Mini Sweater Dress

    It's the season of glam, and you'll shimmer and glimmer in this mini sweater dress! It features a sweetheart neckline, long fitted sleeves, a mini-length hem with a fab side slit, and a bodycon silhouette to show off your curves. The ribbed knit fabric features a sparkly lurex threaded design for a glam touch. Style this sweater dress with strappy mules for a holiday party!

    Fit & Features

    • Sweetheart neckline
    • Long fitted sleeves
    • Mini-length hem, side slit
    • Bodycon silhouette
    • Ribbed knit fabric, lurex threaded design
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1771

    Category Name: Workwear Dresses

    Price: $3.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Abstract Beauty Printed Slit Midi Dress

    Embrace your inner beauty in this abstract printed slit midi dress for any casual occasion! Featuring a flattering sleeveless square neckline perfect for layering, delicate spaghetti straps, and a bodycon fit, this dress flatters every figure. The front slit and midi-length hem add a touch of elegance, while the abstract print and mesh fabric create a unique style. Complete the look in mules and a cropped jacket.

    Fit & Features

    • Abstract print, stretchy mesh fabric, sewn-in knit lining
    • Spaghetti straps
    • Bodycon fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05102-5736

    Category Name: Workwear Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strut And Snap Ribbed Knit Midi Dress

    Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Square neckline
    • Tank shoulder straps
    • Metal button accents
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1167

    Category Name: Workwear Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Make It Work Sleeveless Tank Midi Dress

    Make a bold statement in any setting in this sleeveless midi dress perfect for work or play! The midi dress features a sleeveless square neckline, an underbust seam, tank shoulder straps, a bodycon silhouette that flaunts your curves, and a flirty center back slit accent on smooth woven fabric. Complete the look with pumps and a posh jacket for business mixers and happy hour!

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Underbust seam
    • Bodycon silhouette 
    • Midi-length hem, center back slit
    • Smooth woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2871

    Category Name: Workwear Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Adorable Factor Chiffon Sweetheart Midi Dress

    Raise the bar looking adorable in this chiffon midi dress perfect for upcoming dressy occasions! The midi-length dress features short puff sleeves, a sweetheart neckline, a ruched bust, and a flirty cutout waist to show some skin. The flattering A-line silhouette boasts a playful front slit and a flowy midi hem. Complete the look with cute sandals and jewelry!

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline, stretchy smocked back
    • Ruched bust, cutout waist
    • A-line silhouette, front slit
    • Midi-length hem
    • Chiffon woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-3189

    Category Name: Workwear Dresses

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Sweetheart Mesh Short Dress

    Create a sweet moment with a mini dress that brings the charm! The dress features a sweetheart neckline, short puff sleeves, ruching throughout to enhance curves, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.

    Fit & Features

    • Sweetheart neckline
    • Short puff sleeves
    • Ruching
    • Short-length silhouette
    • Lined mesh fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1698

    Category Name: Workwear Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

  • Casual And Cozy Off-The-Shoulder Sweater Dress

    This on-trend sweater dress is the casual and cozy staple you need this fall and winter season. It features a chic off-the-shoulder neckline, long sleeves, a short-length hem, and a relaxed fit. The ribbed sweater knit fabric offers a moderate stretch. Pair this sweater dress with over-the-knee boots for a stylish and elevated look.

    Fit & Features

    • Off-the-shoulder neckline
    • Long sleeves
    • Short-length hem
    • Relaxed silhouette
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1764

    Category Name: Workwear Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance