Work Dresses & Outfits

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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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.

  • Sharp Lines Asymmetrical Long Sleeve Midi Dress

    Strike a fierce impression in a ribbed knit dress with an asymmetrical off-the-shoulder neckline, a pleated popover accent, fitted long sleeves, and a midi-length hem. Complete the look with strappy heels for the perfect work-to-happy hour look! 

    Fit & Features

    • Ribbed knit fabrication
    • Asymmetrical off-the-shoulder neckline
    • Pleated popover accent at the neckline
    • Long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5947

    Category Name: Work Dresses & Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: M, L, XL

  • Sleek Vibes Long Sleeve Ruched Midi Dress

    Channel sleek vibes in a midi dress that features a boat neckline, fitted long sleeves with thumb holes, and ruching that enhances curves. Complete look with strappy heels to take you from the office to happy hour! 

    Fit & Features

    • Smooth knit fabrication, double-lined
    • Boat neckline
    • Long sleeves with thumb holes
    • Ruching
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3954

    Category Name: Work Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Elevated Button-Down Drop Waist Mini Dress

    So elevated, this adorable mini dress is designed with a textured knit fabric and a sleek button-down front. It features a sleeveless square neckline with tank straps, a drop waist, and a short pleated A-line silhouette for that cute flair.

    Fit & Features

    • Textured knit fabric, sewn-in knit lining
    • Square neckline
    • Tank shoulder straps
    • Button-down front
    • Drop waist
    • Mini-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3842

    Category Name: Work Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Note To Self Ribbed Knit A-Line Mini Dress

    Note to self, this sleeveless mini dress is a must-have for every day! Perfect for any occasion, this stretchy ribbed knit dress will surely become a staple in your wardrobe. It features a crew neckline with tank straps and a flattering A-line silhouette with a flirty front slit on the mini-length hem. Complete the look with an oversized blazer and a sleek necklace.

    Fit & Features

    • Soft and stretchy ribbed knit fabric
    • Crew neckline
    • Tank shoulder straps
    • Front slit
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5632

    Category Name: Work Dresses & Outfits

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Vibes Off The Shoulder Knit Midi Dress

    Keep it sleek and stylish in a ribbed knit dress that features a v-neckline that can be worn off-the-shoulder, fitted long sleeves, and a midi-length hem. Complete the look with sneakers to add a casual touch! 

    Fit & Features

    • Lined ribbed knit fabrication
    • V-neckline and off-the-shoulder 
    • Long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5942

    Category Name: Work Dresses & Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

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

  • Cosmic Chic Tie-Dye Knit Midi Dress

    The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe. 

    Fit & Features

    • Ribbed knit fabrication
    • Scoop neckline
    • Long sleeves
    • Tie-dye pattern
    • Center slit at back of hem
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2132

    Category Name: Work Dresses & Outfits

    Price: $54.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • All Things Cozy High Slit Knit Midi Dress

    Oh-so-cute and cozy, this knit midi dress is a seasonal staple. It features a mock neckline, long fitted sleeves, an asymmetric mid-length hem creating a thigh-high side slit, and a form-hugging silhouette. The ribbed hacci knit fabric has an ultra-soft feel with plenty of stretch. Style this midi dress with knee-high boots for a latte date.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Asymmetric mid-length hem
    • Thigh-high side slit
    • Form-hugging fit
    • Ribbed hacci knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5333

    Category Name: Work Dresses & Outfits

    Price: $24.90

    Availability: In Stock

    Available Color: COGNAC

    Available Size: XS, S, M, L

  • Perfect Curves Ribbed Knit Off-The-Shoulder Midi Dress

    Showcase your perfect curves in this midi dress designed with soft ribbed knit fabric. It features an off-the-shoulder neckline with a chic fold-over design, long fitted sleeves, and a midi-length bodycon silhouette.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5894

    Category Name: Work Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: HEATHERGRAY

    Available Size: XS, S, M, L

  • Adorable Look Plaid Print Strapless Skater Dress

    Adorably chic will be your vibe in this woven skater dress designed with a classic plaid print. It features a strapless subtle sweetheart neckline, a drop waist, and a short pleated skater silhouette for that cute flair.

    Fit & Features

    • Plaid printed woven fabric
    • Strapless sweetheart neckline
    • Back zipper closure
    • Drop waist
    • Mini-length pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5925

    Category Name: Work Dresses & Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

  • Preppy Posh Strapless A-Line Pleated Mini Dress

    Look fabulously mod with this strapless mini dress! Made from smooth woven fabric, discover a next-level fashionista vibe in this dress featuring an A-line silhouette, belt loop accents along the waist, and a pleated mini-length hem for added flair. Complete the look in a blazer for weekend plans!

    Fit & Features

    • Strapless neckline
    • A-line silhouette
    • Belt loop accents along the waist
    • Pleated mini-length hem
    • Smooth woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5444

    Category Name: Work Dresses & Outfits

    Price: $6.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

  • Flawless Allure Crepe Tube Mini Dress

    Keep it flawless in a mini dress that features a sleeveless square neckline and faux front pockets with trendy flap closure. Complete look with a blazer for the perfect workwear outfit. 

    Fit & Features

    • Woven crepe fabrication, moderate stretch, stretchy knit lining
    • Sleeveless square neckline
    • Faux front pockets with flap closure
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05101-3811

    Category Name: Work Dresses & Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: GRAY

    Available Size: XS, S, M, L

  • Chic Staple Ribbed Knit Skater Dress

    A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels.

    Fit & Features

    • Ribbed knit fabric with plenty of stretch
    • Off-the-shoulder neckline, fold-over accent
    • Long fitted sleeves
    • Short-length hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2070

    Category Name: Work Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: OATMEAL, HUNTER, HEATHERGRAY, PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Fabulous Icon Sleeveless Ribbed Knit Midi Dress

    An iconic knit midi dress that can go from day to night! Crafted from soft and stretchy ribbed knit fabric, this sleeveless dress offers a stylish square neckline, a flattering underbust seam, and a bodycon silhouette that will hug your curves in all the right places. Complete the look with a moto jacket and stiletto heels for a chic style.

    Fit & Features

    • Soft, stretchy ribbed knit fabric
    • Square neckline
    • Underbust seam
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-1853

    Category Name: Work Dresses & Outfits

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Sleek Square Neck Bodycon Midi Dress

    Serve a gorgeous sleek silhouette in this brushed knit midi dress featuring a sleeveless square neckline, thin tank straps, and a midi-length bodycon fit to hug your curves. Style with hoop earrings and stiletto heels.

    Fit & Features

    • Brushed knit fabric with knit lining, plenty of stretch
    • Square neckline
    • Thin tank shoulder straps
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5975

    Category Name: Work Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: S, M, L

  • Fresh Breeze Floral Chiffon Midi Dress

    Freshen up your wardrobe for spring to summer with this floral chiffon midi dress - a lovely style for wedding showers and birthday brunches! It features adorable puff short sleeves, a square neck, a flirty bust tie and underbust seam detail, and a slim-fit silhouette with a front slit hem. The airy chiffon fabric features a bouquet floral print pattern. Complete the look with dainty hoop earrings.

    Fit & Features

    • Puff short sleeves, elastic cinched hems
    • Square neck, bust tie, underbust seam detail
    • Back zipper, hook and eye closure
    • Slim-fit silhouette, front slit, midi-length hem
    • Bouquet floral print
    • Sheer chiffon fabric, full knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2130

    Category Name: Work Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Chic Long Sleeve Midi Dress

    Keep it chic in this knit midi dress boasting an off-the-shoulder neckline and trendy button accents that lead to a flirty slit. Pair with boots.

    Fit & Features

    • Ribbed knit fabrication
    • Off-the-shoulder neckline, foldover accent
    • Long sleeves
    • Snap button accents at the hem
    • High side slit
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2137

    Category Name: Work Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: RED, BLACK, PLUM

    Available Size: XS, S, M, L

  • Striped Delight Surplice Collared Mini Dress

    You're sure to have a day full of sweetness in this delightful striped mini dress perfect for upcoming weekend plans! This dress is designed with chic long sleeves with button cuffs, along with a flattering collar V-neckline and wrap tie waist belt for that cinched look. The surplice mini-length hem adds a touch of sass while the pleated form-hugging fit accentuates your curves. Complete the look in clear sandals and earrings.

    Fit & Features

    • Striped non-stretch woven lightweight fabric
    • Collared V-neckline
    • Long sleeves with buttoned cuffs
    • Wrap tie waist belt with pleating
    • Surplice mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5610

    Category Name: Work Dresses & Outfits

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

  • She's The Main Rib Knit Strapless Midi Dress

    Flaunt your look with ease and chicness with this midi dress this season! The knee-length dress features a strapless neckline, a flattering bodycon silhouette, and a fitted maxi-length hem on soft and stretchy rib knit fabric with a short knit lining. Style with the matching bolero and heels for weekend plans!

    Shop Matching Bolero: She's The Main Rib Knit Slouchy Bolero

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Fitted midi-length hem
    • Soft and stretchy
    • Rib knit fabric, short knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5872

    Category Name: Work Dresses & Outfits

    Price: $33.90

    Availability: In Stock

    Available Color: GRAY, IVORY, SAGE, BROWN-2

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

  • Basic Bae Square Neck Tank Sweater Mini Dress

    Fall for this basic sweater mini dress to meet all of your day-to-night fashion needs! Crafted from a luxe rib knit fabric with the perfect amount of stretch, this short dress is designed to fit your body like a glove. Featuring a classic square neckline for a show of skin, comfortable tank shoulder straps, and a bodycon silhouette that'll turn heads! Style this mini dress with strappy heels to elevate your look.

    Fit & Features

    • Sweater rib knit fabric with stretch
    • Tank shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-1838

    Category Name: Work Dresses & Outfits

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Draw The Line Striped Sweater Midi Dress

    Draw the line at basic and reach for this sensational striped sweater dress! It features a trendy off-the-shoulder neckline, fitted long sleeves, a flattering bodycon silhouette, and dual tie-back closures, and a cutout design. Complete the look with a chic crossbody bag for day or evening plans.

    Fit & Features

    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Dual tie-back closures, cutout design
    • Bodycon silhouette
    • Midi-length hem
    • Striped pattern, stretchy sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5360

    Category Name: Work Dresses & Outfits

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

  • Attract And Allure Marble Print Midi Dress

    Attract and allure in this marble print midi dress that puts your curves on display! It features a high crew neckline, long fitted sleeves, a midi-length hem with a form-hugging silhouette, and an all-over trendy marble print pattern. The sheer mesh fabric includes a full-length sleeveless knit lining. Style this mid-length dress with clear heel mules for a cool-girl vibe for a rooftop bar!

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Midi-length hem, form-hugging fit
    • Marble print, sheer mesh fabric
    • Full-length sleeveless knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5403

    Category Name: Work Dresses & Outfits

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

  • Abstract Moment Mesh Mock Neck Midi Dress

    Step out in this stylish mesh midi dress and not miss a single moment to have all eyes on you! The knee-length dress features a feminine mock neck with back button closures, fitted sheer long sleeves, and bodycon silhouette with abstract print on mesh fabric. Complete the look with gold hoop earrings for an art gallery opening and dinner downtown!

    Fit & Features

    • Mock neck, back button closures
    • Fitted sheer long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5294

    Category Name: Work Dresses & Outfits

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

  • Cozy Luxe Cable Knit Off-The-Shoulder Midi Dress

    Show off a luxe look while still keeping it cozy in this soft cable knit midi dress is designed with an off-the-shoulder fold-over neckline, long fitted sleeves, and a high front slit to accent the midi-length form-hugging silhouette. Style with knee-high boots or strappy heels!

    Fit & Features

    • Ribbed cable knit fabric, plenty of stretch
    • Off-the-shoulder fold-over neckline
    • Long fitted sleeves
    • High front slit
    • Midi-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2106

    Category Name: Work Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: OATMEAL

    Available Size: S

  • Chic Flowy Chiffon Midi Dress

    Get the perf semi-formal look in this effortlessly chic chiffon midi dress. It features a sleeveless sweetheart neckline with a padded bust, spaghetti straps, a flattering high waist seam, and a mid-length skirt with a front slit and a flowy A-line silhouette. Style this dress with sleek earrings and cute heels.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Built-in padded bust
    • Adjustable spaghetti straps
    • Partially smocked back, zipper and hook-eye closure
    • High waist seam, flowy A-line silhouette, front slit
    • Sheer chiffon fabric, inner knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2187

    Category Name: Work Dresses & Outfits

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale