Workwear Dresses

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.