27 Fall and Winter Dress Deals I’m Buying Ahead of Cyber Monday—Starting at $29

Melony Forcier
·9 min read

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J.Crew, Madewell, and Nordstrom are brimming with cozy styles.

Madewell/ InStyle

Madewell/ InStyle

Between holiday parties, winter weddings, and New Year celebrations, this is by far the busiest time of the year. That being said, it can feel overwhelming for us fashion-minded individuals to pick out a new outfit for every occasion. While I’m always one for outfit repeating, I like adding a few new pieces to my wardrobe during the holiday season. So, I’m using this shopping weekend to find unbeatable dress deals for every occasion.

Whether it’s a cozy sweater dress or a sequin maxi dress, I set out to find the steepest markdowns on fall and winter dresses at my favorite retailers, including Amazon, Nordstrom, J.Crew, and more. Ahead, I’ve rounded up 27 of the best dress deals to shop before Cyber Monday, starting at $29.

Best Overall Early Cyber Monday Fall and Winter Dress Deals

Madewell Denim Button-Front Mini Shirtdress

Madewell

Madewell

This weekend, I plan to fill my shopping carts with everything from sparkly holiday dresses to warm sweater dresses. I found deals up to 55 percent off from my go-to retailers, including J.Crew and Banana Republic. Plus, I discovered many expensive-looking dresses for under $100 that would seriously shock my friends if they heard the price tag.

Best Early Cyber Monday Sweater Dress Deals

From holiday festivities to last-minute shopping outings, sweater dresses are an easy (and comfy) outfit that will carry you through fall and winter. I found cozy sweater dresses from Amazon, Nordstrom, and more marked down ahead of Cyber Monday, starting at just $29.

Prettygarden Sweater Dress

Amazon

Amazon

Keep comfortable in this stylish mini sweater dress from Prettygarden. The knit dress features a V-neckline, a button-down front, and a flattering cinched waistline. You can shop the look in 14 colors, but I’m partial to the khaki shade, which has an elevated, quiet-luxury feel.

Pink Queen Loose Turtleneck Pullover Sweater Dress

Amazon

Amazon

With over 13,000 five-star ratings, this turtleneck sweater dress is a favorite among Amazon shoppers. The cozy oversized sweater can be worn as a mini dress or with leggings for a more casual look, and it has side pockets. For under $30, what more can you ask for?

Banana Republic Merino Mini Sweater Dress

Banana Republic

Banana Republic

Luxurious and super soft, this Merino wool sweater dress is perfect for any fall or winter occasion. The fit-and-flare mini has a wide turtleneck neckline and seam detailing down the front and the back. Style yours with black tights and tall boots for a stylish night-out look that is ideal for colder weather.

Mango Long-Sleeve Mini Sweater Dress

Nordstrom

Nordstrom

This easy-to-wear long-sleeve sweater dress will keep you warm and can take you from day to night all winter. Shop the crewneck dress in a festive green shade, or keep it classic with a timeless little black dress.

Best Sweater Dress Deals

Best Early Cyber Monday Holiday Dress Deals

Whether you’re looking for a holiday party ensemble or a glittering outfit to ring in the year, there’s no shortage of holiday dress deals this weekend. Find elegant long-sleeve dresses that keep you warm and fashionable, or opt for a statement-making sequin number for a touch of sparkle.

Dokotoo V-Neck Midi Dress

Amazon

Amazon

Slip into this festive skater dress for a winter wedding or holiday celebration. Falling around mid-calf, this polished dress features a wrap-waist detail, ruffled sleeves, and a deep V-neckline.

Banana Republic Crepe Twist-Shoulder Dress

Banana Republic

Banana Republic

Turn heads in this stunning crepe dress from Banana Republic, currently 40 percent off. The holiday party-ready dress has a twist-shoulder neckline and a flattering draped silhouette with bias-cut panels.

Banana Republic Stretch-Sequin Maxi Dress

Banana Republic

Banana Republic

Make the whole place shimmer in this eye-catching sequin maxi dress. The stretch fit will keep you comfy and on the dance floor all evening. The dress also comes in three luxe-looking metallic shades, including Cinnamon Dolce Latte and Chocolate Ganache Brown.

J. Crew Long-Sleeve Dress

J.Crew

J.Crew

This sophisticated long-sleeve dress is made from comfortable jersey crepe with cinched side detailing. J.Crew shoppers say it is “so flattering” and “versatile,” making it an excellent choice for holiday parties and beyond.

Best Holiday Dress Deals

Best Early Cyber Monday Mini Dress Deals

Grab your tights and celebrate the season in a fun, flirty mini dress. From sleek shift dresses to denim shirt dresses, there’s a dress style for everyone and every occasion, whether you’re looking for a sophisticated party dress or an everyday piece.

Mango Button Tab Shift Minidress

Nordstrom

Nordstrom

This effortlessly chic minidress from Mango is the perfect work dress to take you through fall and winter. The sleeveless shift dress is made from suiting fabric that offers a bit of stretch for a comfortable yet put-together look.

J.Crew Elena Long-Sleeve Mini Dress

J. Crew

J. Crew

Leopard print is having a moment right now, so hop on the trend with this short and sweet J.Crew mini dress. It’s made from an elegant, subtly sheer chiffon and is currently on sale for 55 percent off.

Madewell Denim Button-Front Mini Shirtdress

Madewell

Madewell

Keep things casual with this weekend-worthy denim button-front dress from Madewell. The best-selling mini is 40 percent off right now, so I’m adding it to my shopping cart immediately.

Best Mini Dress Deals

Best Early Cyber Monday Midi Dress Deals

Whether you dress them up or down, midi dresses are a versatile option that can take you from work, happy hour, or a holiday party. I found a variety of mid-length dresses on sale this weekend, including elevated party dresses, semi-formal wedding guest dresses, and knit shirtdresses.

Madewell Puff-Sleeve Sweetheart Midi Dress

Madewell

Madewell

Add a touch of romance to your fall wardrobe with this sweetheart neckline mini dress from Madewell. It has a peekabo side slit and subtle puff sleeves for an elegant yet playful fall look.

Banana Republic Jersey Knit Shirtdress

Banana Republic

Banana Republic

Allow me to introduce you to your new go-to dress. This knit shirtdress from Banana Republic has all the makings of a closet staple. Made from a wrinkle-resistant jersey material, the stretchy dress can seamlessly be dressed up or down.

Eloquii Cross Front Midi Dress

Nordstrom

Nordstrom

Whether you’re attending a winter wedding or searching for a new occasion dress, this Eloquii midi dress is a great option. The blouson sleeves add a bit of movement to the dress, while the adjustable ties at the waist allow you to customize the fit.

Best Midi Dress Deals

Best Early Cyber Monday Maxi Dress Deals

From sweater dresses to pleated frocks, I searched far and wide for the best maxi dresses on sale this holiday shopping weekend. As someone on the shorter side, finding a maxi dress that I don’t need altering can be difficult, but these options include everything from ankle-grazing styles to long sweater dresses.

Prettygarden Puff Sleeve Maxi Dress

Amazon

Amazon

Transition from fall to winter in style with this cute puff-sleeve maxi dress. The smocked dress features an empire waistline and a smocked bodice.

J.Crew Pleated Ballet Dress

J.Crew

J.Crew

Embrace your inner ballerina with this long pleated dress from J.Crew. Leotards inspire the fitted, long-sleeve bodice, while the bottoms feature a full-length, flowy pleated skirt that might give you the urge to twirl.

Madewell Sweater Maxi Dress

Madewell

Madewell

Warm up by the fireplace in this chic sweater maxi dress marked down to less than $100 ahead of Cyber Monday. The long dress is made from a cozy cotton-blend material, with a ribbed crewneck and long sleeves.

Best Maxi Dress Deals

I hope this curated list of fall and winter dress deals helped you narrow your search in the sea of markdowns, from Black Friday to Cyber Monday. Taking on the season in style, whether in a cozy sweater dress or a head-turning holiday number, is always a little easier with wallet-friendly options.

Zeagoo Oversized Sweater Vest Dress

Amazon

Amazon

Spanx AirEssentials Pleated Dress

Nordstrom

Nordstrom

Madewell Sleeveless Satin Midi Dress

Nordstrom

Nordstrom

Banana Republic Jersey Knit Twist-Front Maxi Dress

Banana Republic

Banana Republic

Melony Forcier is a shopping writer with over four years of experience. She’s tested fashion, beauty, and home finds, and specializes in staying up-to-date on the latest must-have items, from celebrity-loved fashion trends to the season’s hottest accessories.

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