From workdays to weekend plans and even last-minute errands, my schedule requires winter dresses that can do all three without any extra effort. After trying countless styles as a shopping writer, I’ve become particular about exactly what actually earns my closet space. If a style isn’t comfortable and doesn’t come with pockets, it simply won’t make the cut.
This roundup includes the 17 winter picks I reach for most, including cozy sweater styles, tunic knit midis and easy wrap silhouettes. Each one is easy to throw on with boots or sneakers, layers well under coats and looks put-together with little effort. Best of all, every pick has functional pockets — and costs under only $40!
Winter Dresses With Pockets for Under $40
1. Our Favorite: Checking all of the boxes, this bestselling tunic dress is comfy, flattering and shoppers love the quality of the material, saying it’s “soft and comfy!”
2. Casual-Chic: This babydoll sweater dress is the kind I’d throw on for a coffee date when I still want to feel polished.
3. Trending Tunic: This flattering tunic dress is a top favorite of Amazon shoppers, and honestly, I get the hype. The ribbing is ultra-flattering, and shoppers say the flowy fit is, too.
4. Loose and Slimming: This loose midi dress sits comfortably on the body and proves that more relaxed styles can be just as flattering as form-fitting options.
5. Deal Alert: If you’re watching your budget, you’re going to want to pick up this flowy midi dress that’s now discounted to 53% off.
6. Plaid-Perfect: This plaid mini dress is ideal for those who love a cozy vibe. The slightly stretchy fabric makes this easy to style with leggings, allowing you to wear it all year round.
7. Brunch Beauty: Designer for brunch moments, this elegant maxi dress blends a flattering cinched waistline with a tiered, puff-sleeve design that looks far more expensive than it is.
Nordstrom Dropped New Elevated Pieces — Here’s What I’m Buying Before Everyone Else
8. Swiss Dot Stunner: With its cinched waist, this Swiss-dot midi dress adds boutique-level visual texture while helping create a more defined waistline.
9. Midi Must-Have: Thanks to a flared hem and ribbed fabric, this comfy midi dress is polished enough for daytime plans while still maintaining all-day comfort.
10. Office-Ready: This mock neck sweater dress has a modest design that’s office-appropriate, and a soft and stretchy knit fabric that keeps you comfortable all day.
11. Wedding Guest Winner: If you’re on the hunt for a winter wedding guest dress, you’re going to want to take a look at this pleated maxi dress that’s made with a flattering fit-and-flare design that accentuates the silhouette.
12. Options Galore: If you’re anything like me and love having choices, this comfy midi dress comes in 10 different options (like sea blue to beige) to pick from.
13. Curve-Flattering: This flattering wrap dress is designed to flatter, complete with a slimming V-neckline, cinched waist and flared skirt.
14. Pretty Prints: I’m a sucker for a good print moment, and this long-sleeve midi delivers with several options to pick from, like florals, polka dots and more.
15. Floral Favorite: With its relaxed, easy-to-style design, this floral T-shirt dress works with a cardigan now, and can be worn solo when it warms up.
16. Make it a Maxi: Designed with a bold floral print, this T-shirt maxi dress gives coverage, comfort and personality all in one easy piece.
17. Trusty T-Shirt: With its comfy, throw-on design and soft, stretchy fabric, this crewneck T-shirt dress is made for travel, errands and busy days.
It’s Official: Here Are the 17 Best Jeans to Pair With Sneakers in 2026
Us Weekly has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more!
