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.

  • Major Charm Crepe One Shoulder Dress

    Bring major charm in this one-shoulder midi dress showcasing a sleek and sultry silhouette perfect for flaunting curves! It features a sleeveless bodice with a single spaghetti strap, a tie-front waist belt, and a front-side slit accent on crepe fabric. Complete the look in simple nubuck block heels.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single spaghetti strap
    • TIe-front waist belt
    • Bodycon silhouette
    • Front side slit. midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1699

    Category Name: Workwear Dresses

    Price: $28.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Stroll Along Surplice Tie Waist Mini Dress

    Stroll along the city streets in this casual mini dress perfect for a day out! The mini dress features relaxed long sleeves with banded cuffs, a V-neckline with a surplice accent, a tie-waist belt, and a flattering bodycon fit on stretchy knit fabric. Complete the look with a crossbody bag.

    Fit & Features

    • Relaxed long sleeves, banded cuffs
    • V-neckline, surplice accent
    • Tie-waist belt
    • Bodycon fit
    • Mini-length hem
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5354

    Category Name: Workwear Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Zadie Formal High-Slit Midi Dress

    Special Occasion 

    Impress in an elegant midi dress that is simply sophisticated! Zadie features a strapless square neckline, flexible boning, a draped accent at the bodice, and a midi-length silhouette accented with a high side slit. The midi dress is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete the look with rhinestone heels and an anklet.

    Fit & Features

    • Strapless square neckline
    • Draped accent on bodice, flexible boning
    • Back zipper closure 
    • Form-hugging fit, midi-length silhouette, high side slit
    • Crepe fabric with moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-2067

    Category Name: Workwear Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: HUNTER-2

    Available Size: S

  • It's A Must Collared Denim Mini Dress

    This denim mini dress is a must for curating a cute and trendy lineup this season! The short dress features long sleeves, a collar neckline, zipper front closure, dual flap pockets with snap-button closures and lower pockets, an elasticized waist with belt loop accents, a bodycon fit, and a mini-length hem. Complete the look in pointed-toe booties for a day out with friends!

    Fit & Features

    • Long sleeves, collar neckline
    • Zipper front closure
    • Flap pockets with snap-button closures
    • Lower pockets
    • Bodycon fit, mini-length hem
    • Rigid denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5364

    Category Name: Workwear Dresses

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Stylish Sleeveless Ribbed Knit Midi Dress

    Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • High front slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1645

    Category Name: Workwear Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: WHITE, BLACK, DARK, DENIM, RED, MAUVE

    Available Size: M, L, XS, S

  • Make A Debut Plaid Strapless Pleated Mini Dress

    Make a debut in classic plaid and on-trend silhouette! This plaid mini dress is sure to stand out from any crowd. Featuring a strapless neckline, form-hugging bodice, belt loop accents, and a flirty pleated mini-length hem. Complete the look in lug boots for an edgy vibe!

    Fit & Features

    • Strapless neckline
    • Back zipper closure
    • Form-hugging bodice
    • Belt loop accents
    • Pleated mini-length hem
    • Plaid print, woven fabric, knit lining at the bust, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5415

    Category Name: Workwear Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Trendy Striped Slit Maxi Dress

    A trendy maxi dress features a flattering square neckline, form-hugging fit, and a high front slit to show off your shoes. Perfect for styling with a denim jacket and sandals.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Square neckline, spaghetti straps
    • High front slit
    • Form-hugging maxi-length fit
    • Runs true to size

    Style Number/Barcode: 05102-5867

    Category Name: Workwear Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make An Appearance Lace-Up Sweater Mini Dress

    Make an appearance in this sweater mini dress for dates to dinners! The mini dress features fitted long sleeves with flared cuffs and eye-catching lace-up packets, a mock neckline, and a flattering bodycon silhouette, on rib knit sweater fabric. Complete the look with simple hoop earrings and heels.

    Fit & Features

    • Fitted long sleeves
    • Flared cuffs, lace-up plackets
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1741

    Category Name: Workwear Dresses

    Price: $3.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Babe With Taste Buckle Strap Pleated Mini Dress

    Let everyone know you're a babe with taste in this pleated mini dress! Made from a twill woven fabric for structure and has a stretchy knit lining for coverage. With a square neckline and seam detailing, this dress exudes style. The adjustable buckle shoulder straps provide a customizable fit, while the fitted bodice and pleated mini-length hem flatter your figure. Complete the look with sunglasses and a purse!

    Fit & Features

    • Twill woven fabric, stretchy knit lining
    • Square neckline
    • Back zipper closure
    • Adjustable buckle shoulder straps
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5629

    Category Name: Workwear Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Impress Me Pinstripe Strapless Mini Dress

    This pinstripe mini dress is sure to impress! Featuring a strapless foldover neckline with non-slip grip lining, a stretchy smocked back, form-hugging silhouette, and a flirty front slit along the hem. Complete the look in a cropped blazer for a posh vibe!

    Fit & Features

    • Strapless foldover neckline
    • Non-slip grip lining
    • Stretchy smocked back
    • Form-hugging silhouette, front slit, mini-length hem
    • Back zipper and hook-eye closure
    • Pinstripe print, woven fabric, and lining
    • Runs true to size

    Style Number/Barcode: 05102-5469

    Category Name: Workwear Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

  • Good Times Bodycon Abstract Print Mini Dress

    A mini dress that calls for good times only at casual parties or weekend plans! Designed with an alluring abstract print on mesh fabric, this dress is both chic and versatile. The sleeveless crew neckline and bodycon silhouette highlight your curves, while the side ruched seams flatter your figure. Complete the look with a mini shoulder bag and heels.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Side ruched seams
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5606

    Category Name: Workwear Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S

    Product Badge:
    • Sale
  • Your Needs Met Sleeveless Slit Midi Dress

    A sleeveless midi dress that meets all of your style needs! This knee-length dress features a square neckline, wide shoulder straps, a flattering bodycon silhouette, and a front slit on woven fabric. Style this midi dress with sleek stiletto heels for a cocktail party or rehearsal dinner!

    Fit & Features

    • Sleeveless square neckline
    • Wide shoulder straps
    • Back zipper closure
    • Bodycon silhouette, front slit
    • Midi-length hem
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2884

    Category Name: Workwear Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Chic Floral Chiffon Midi Dress

    Enchanting and chic, this floral chiffon midi dress is perfect for a garden wedding. It features a sleeveless sweetheart neckline with a bust outline, adjustable spaghetti straps, a high waist seam, a smocked back panel with a zipper closure, a midi-length hem with a high front slit, and a flowy A-line silhouette. The airy chiffon fabric features a romantic blooming floral print alongside a dainty flower pattern. Style with clear block heels.

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust and outline
    • Adjustable spaghetti straps
    • High waist seam, stretchy smocked back, zipper and hook-eye closure
    • Midi-length hem
    • Front slit, A-line silhouette
    • Floral print, chiffon fabric, smooth stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-3213

    Category Name: Workwear Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS

    Product Badge:
    • Sale
  • Jullian Formal Crepe Off-The-Shoulder Midi Dress

    Special Occasion

    A timeless addition to your wardrobe, the Jullian formal midi dress is beautiful and perfect for banquets or formal parties! With its foldover off-the-shoulder neckline, bodycon fit, and midi-length hem with a front slit - you'll exude classic sophistication. The formal midi dress is composed of a sleek crepe fabric with a bust knit lining and plenty of stretch for comfort! Complete the look with strappy block heels.

    Fit & Features

    • Foldover off-the-shoulder neckline
    • Bodycon fit
    • Front slit, midi-length hem
    • Crepe fabric, bust knit lining
    • Strapless bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-2035

    Category Name: Workwear Dresses

    Price: $24.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Spirit Collared Midi Dress

    Get some pep in your step by styling this casual midi dress for art shows or family dinners! The mid-length dress features a collared V-neckline, long fitted sleeves, and a bodycon silhouette on stretchy ribbed knit fabric. Style with knee-high boots to complete the look!

    Fit & Features

    • Collared V-neckline
    • Long fitted sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5214

    Category Name: Workwear Dresses

    Price: $19.00 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

    Product Badge:
    • Sale
  • Chic In The City Turtleneck Mini Dress

    You'll look chic as you take a stroll in the city in this trendy turtleneck mini dress! It features a turtleneck that you can fold over, long fitted sleeves, ruching down the side seams, a mini-length hem, and a bodycon silhouette to showcase your curves. The soft brushed knit fabric offers plenty of stretch for comfortable wear. Style this mini dress with a faux leather blazer and over-the-knee boots for a cute fall 'fit.

    Fit & Features

    • Turtleneck
    • Long fitted sleeves
    • Ruched side seams
    • Mini-length hem
    • Bodycon silhouette
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5220

    Category Name: Workwear Dresses

    Price: $17.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swirl Fun Chain Strap Midi Dress

    Perfect for your next getaway, this swirl midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. The dress is composed of a swirl print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless square neck
    • Half chain, adjustable spaghetti straps
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Swirl print
    • Slinky knit fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5301

    Category Name: Workwear Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Annika Formal Mid-Length Bandage Dress

    Special Occasion

    Create the snatched silhouette of your dreams in the iconic Annika formal mid-length bandage dress! She features a sleeveless square neckline, spaghetti straps, a hidden back zipper closure, a midi-length hem with a chic back slit accent, and a bodycon silhouette that will hug your figure. The bandage knit fabric offers a smooth and sculpted look with plenty of stretch. Style with clear heels for your next cocktail hour.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Hidden back zipper, hook and eye closure
    • Midi-length hem, back slit
    • Bodycon silhouette, sculpted look
    • Bandage knit fabric, plenty of stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1570

    Category Name: Workwear Dresses

    Price: $9.97 $99.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Day Dreamer Strapless Abstract Midi Dress

    Make your daydream come true and wear this mesh midi dress for a gorgeous look this weekend! It features a strapless neckline with non-slip grip lining, flexible boning inserts along the bodice for structure, and ruched seams to accentuate your figure along the bodycon silhouette. The dress is designed with an abstract print on mesh fabric with a sewn-in knit lining. Complete the look with hoop earrings.

    Fit & Features

    • Strapless neckline, non-slip grip lining
    • Flexible boning inserts
    • Side zipper and hook-eye closure
    • Ruched seams, bodycon silhouette
    • Midi-length hem
    • Abstract print, mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5363

    Category Name: Workwear Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

  • Only Chic Vibes Vest Dress

    Bring only chic vibes in this on-trend fitted vest dress. It features a sleeveless bodice, a V-neckline with a lapel collar, a button-down front, and a mini-length silhouette. Style this crepe-woven dress with an embossed handbag and strappy heels.

    Fit & Features

    • Sleeveless bodice
    • V-neckline, lapel collar
    • Button-down front
    • Mini-length hem, fitted silhouette
    • Crepe-woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1580

    Category Name: Workwear Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Midi Sweater Dress

    This adorable retro print sweater dress is giving major weekend getaway vibes! It features a sleeveless scoop neckline, a front O-ring accent with a small keyhole cutout, tank shoulder straps, a scoop-back design, a midi-length hem, and a form-hugging silhouette. The sweater knit fabric features a trendy retro-inspired multi-print pattern. Style with espadrille sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Front O-ring accent, small keyhole cutout
    • Tank shoulder straps, scoop-back design
    • Midi-length hem, form-hugging fit
    • Retro-inspired multi-print pattern
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1642

    Category Name: Workwear Dresses

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dreamy In Floral Satin Midi Dress

    Create a dreamy look in this floral satin midi dress for brunch or bridal showers! It features a sleeveless cowl neckline, adjustable spaghetti straps, a curve-hugging slim silhouette, and a flirty side slit accent. Complete the look in heeled mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Curve-hugging, slim silhouette
    • Side slit accent
    • Midi-length hem
    • Floral print, silky satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4985

    Category Name: Workwear Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Styling Ribbed Knit Midi Dress

    This casual-chic ribbed knit midi dress will create effortless styling for everyday wear! It features a sleeveless scoop neckline, tank shoulder straps, a midi-length hem that hits mid-calf, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered charm necklace and clear mules.

    Fit & Features

    • Sleeveless scoop neckline, scoop back design
    • Tank shoulder straps
    • Midi-length hem
    • Form-hugging fit
    • Ribbed knit fabric, top lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5037

    Category Name: Workwear Dresses

    Price: $19.00 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Halter Sweater Mini Dress

    Leave an impression in this sweater mini dress for dates or weekend getaways! The rib knit dress features a sleeveless halter neckline, a partially open back, a bodycon silhouette, and a mini-length hem with a flirty slit. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless halter neckline
    • Partially open back
    • Bodycon silhouette
    • Mini-length hem, slit accent
    • Rib-knit sweater fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1424

    Category Name: Workwear Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance