How To Style A Midi Sweater Dress Outfit + 13 Flattering Midi Sweater Dresses

I adore wearing midi sweater dresses in winter for a chic, yet comfortable look. For those who are unsure, a midi sweater dress is a woven or knit dress that falls below your knees, but is higher than your ankles. Basically, it dances around the middle of your tibia bone. My preferred length is when it hits your mid to lower calf. You don’t want a longer length or the dress starts to butt up against your shoes. For the best look, you never want your sweater dress to touch your shoes. Keep reading for more tips on how to style a midi sweater dress, including what shoes, outerwear, and jewelry to wear for the perfect midi sweater dress outfit.

How To Style A Midi Sweater Dress Outfit: The Shoes

I advise skipping the sleek leather pumps and dainty flats and steering yourself towards heartier footwear. If you want to wear heels, go for a chunky heel like Linda Paolo’s block heel loafer, but my all-time favorite shoe to wear with a midi sweater dress is a sleek square toe or pointed-toe bootie, like my navy Steve Maddens pictured above. An open-toe bootie could work, too, but I like to skip round-toe booties since they are not as flattering. Chunky loafers also work with a midi sweater dress, but again, they’re not as flattering as a sharp bootie look. I also recommend skipping wedges with a midi sweater dress. When in doubt, go for the booties!

Midi Sweater Dress Outfit: The Outerwear, Jewelry & Tights

Now that we’ve figured out what shoes to wear with a midi sweater dress, let’s discuss how to style the rest of your outfit…

• Outwear: I love to pair trench coats with midi sweater dresses. The key is the length. You want your outerwear to hit past the bottom of your hips. It can go as long as your ankles.
• Jewelry: You can wear statement earrings, like I’m doing above, or go with the more on-trend look of layered delicate necklaces with stacking rings. I generally skip bracelets since midi sweater dresses tend to have sleeves.
• Tights or no tights? I live in San Diego, so I go bare leg, but in cities that drop below 60° throw on a pair of tights. They should match your skin tone, shoe, or dress, and can be opaque, sheer, or textured. You can even put leggings on underneath your midi sweater dress if the dress is made from a thicker fabric or has a flared skirt.

Flattering Midi Sweater Dresses

Now that you know how to style your midi sweater dress, let’s get you a flattering dress to wear this winter! Below are all the best midi sweater dresses I’ve come across when shopping for my clients this year. I’ll continue to update this post with flattering dresses as I find them.

Available at Nordstrom.

Sizing: XS-XL

Material: 87% rayon, 13% polyester

Ann Taylor Cashmere Ribbed Cardigan Dress

Available at Ann Taylor.

Sizing: XXS-XXL

Material: 100% cashmere

PAIGE Bel Dress

Available at PAIGE and Amazon.

Sizing: XXS-XL

Material: 52% acrylic, 28% polyester, 20% nylon

Available at Nordstrom and Bloomingdale’s.

Sizing: M-XL

Material: 100% cashmere

Anthropologie Mare Mare Scoop-Neck Knit Midi Dress

Available at Anthropologie.

Sizing: XXS-XL

Material: 30% viscose, 27% polyester, 25% acrylic, 18% nylon

Glade Rachel Knitted Shirt Dress

Available at Boden.

Sizing: 0-22

Material: 70% cotton 30% wool

Available at Nordstrom.

Sizing: XXS-XXL

Material: 70% wool, 30% recycled cashmere

Available at Nordstrom.

Sizing: XS-L

Material: 48% cotton, 32% nylon, 20% linen

Available at Nordstrom, Bloomingdale’s, Saks Fifth Avenue, Shopbop, and Simon Miller.

Sizing: XS-XL

Material: 50% polyester, 45.2% acrylic, 4.8% lambswool

WAYF Morgan Long Sleeve Midi Sweater Dress

Available at Nordstrom.

Sizing: XS-M

Material: 45% acrylic, 28% nylon, 27% polyester

Lela Rose Off the Shoulder Long Sleeve Milano Knit Dress

Available at Nordstrom.

Sizing: XS-L

Material: 50% rayon, 40% viscose, 10% polyester

SER.O.YA Phyllis Metallic Knit Cardigan

Available at Saks Fifth Avenue and FWRD.

Sizing: XS-XL

Material: 74% Viscose , 26% Metallic

Available at Nordstrom, Saks Fifth Avenue, and Neiman Marcus.

Sizing: XS-XL

Material: 33% viscose, 23% nylon, 20% wool, 20% cotton, 4% cashmere

 

Photos by Dayley Photography