Embrace the changing seasons with our collection of plus size cool weather dresses, designed to keep you stylish and comfortable as temperatures drop. Each piece in this curated selection effortlessly balances warmth and fashion, making it easy to transition from cozy indoor gatherings to brisk outdoor strolls. Discover a variety of flattering silhouettes, rich textures, and versatile designs that pair perfectly with your favorite boots and accessories. Whether you're dressing up for a special occasion or seeking everyday elegance, our plus size cool weather dresses are crafted to enhance your confidence and fit seamlessly into your wardrobe.

Best Seller

Cable Sweater Dress
by Jessica London

~~$119.99~~

From $79.99
Save up to $40 (33%)
Best Seller

Double-V Maxi Dress
by Jessica London

~~$109.99~~

From $38.49
Save up to $72 (65%)
Best Seller

2-Piece Sweater Dress
by Jessica London

~~$169.99~~

From $119.99
Save up to $50 (29%)
Jacket Dress Set
by Roaman's

~~$89.99~~

From $69.99
Save up to $20 (22%)
Best Seller

Pullover Wrap Sweater Dress
by Jessica London

~~$129.99~~

From $44.98
Save up to $85 (65%)
Best Seller

2-Piece Sweater Jacket Dress
by Jessica London

~~$159.99~~

From $99.99
Save up to $60 (38%)
Best Seller

French Terry Hooded Sweatshirt Dress
by ellos

~~$62.90~~

From $44.03
Save up to $19 (30%)
Best Seller

Cotton Ribbed Sweater Dress
by Jessica London

~~$99.99~~

From $69.99
Save up to $30 (30%)
Best Seller

Scoop-Neck Sweater Dress
by Jessica London

~~$99.99~~

From $69.99
Save up to $30 (30%)
Best Seller

Cable Knit Cape Sweater Dress
by Jessica London

~~$169.99~~

From $58.98
Save up to $111 (65%)
Best Seller

Textured Cowlneck Sweater Dress
by Jessica London

~~$99.99~~

From $34.98
Save up to $65 (65%)
Best Seller

2-Piece Sweater Jacket Dress
by Jessica London

~~$159.99~~

From $59.98
Save up to $100 (63%)
Tiered Lorelai Maxi Dress
by June+Vie

~~$129.99~~

From $90.99
Save up to $39 (30%)
Best Seller

Button Front Sweater Dress
by Jessica London

~~$129.99~~

From $44.98
Save up to $85 (65%)
Best Seller

Smocked Waist Midi Dress
by ellos

~~$85.90~~

From $60.13
Save up to $26 (30%)
Best Seller

Two Piece Sweater Dress Set
by Jessica London

~~$169.99~~

From $83.99
Save up to $86 (51%)
Best Seller

Puff-Sleeve Shirtdress
by June+Vie

~~$159.99~~

From $49.98
Save up to $110 (69%)
Best Seller

Belted Cable Sweater Dress
by Jessica London

~~$129.99~~

From $35.98
Save up to $94 (72%)
Best Seller

Hooded Velour Lounge Dress
by ellos

~~$59.90~~

From $35.94
Save up to $24 (40%)
Best Seller

Chiffon-Paneled Midi Sweater Dress
by June+Vie

~~$189.99~~

From $59.98
Save up to $130 (68%)
V-Neck Midi Sweater Dress With Side Slits
by ellos

~~$109.90~~

From $65.94
Save up to $44 (40%)
Best Seller

V-neck Tiered Midi Dress
by ellos

~~$84.90~~

From $24.98
Save up to $60 (71%)
Tartan Fit-And-Flare Sweater Dress
by Roaman's

~~$99.99~~

From $79.99
Save up to $20 (20%)
Best Seller

Tiered Print Lounger
by Only Necessities

~~$54.99~~

From $39.99
Save up to $15 (27%)

Credit Card

Enjoy these top rewards and special benefits when you use the Roaman's Platinum credit card:

Earn Rewards Every Time You Shop

Free Shipping up to 4 Times a Year

A Special Birthday Surprise!

Shipping To

Customer Service

Quick Links

Plus Size Cool Weather Dresses 150 Items

Request a Free Catalog

Roaman's Platinum Credit Card

Customer Service

My Account

Credit Card

Gift Cards

Catalog

Roaman's

Shipping To

Plus Size Cool Weather Dresses 150 Items

Best Sellers

Related Pages