Winter Maxi Dresses For Every Body Type

This winter we wanted to highlight dresses for every body, whether you’re petite or tall and no matter what your shape may be.
Kim Hancher

There’s no denying that a good dress can offer an easy styling solution. The one-and-doneness of it - just add shoes and jewelry – has saved many overbooked women who are getting to their next destination in a pinch. And, especially in midlife, a dress can offer salvation to the most style-challenged among us.

Today, dresses are for every day.

They come in dozens of styles and fabrications, so no matter your personal aesthetic (classic, boho, uber femme) or your lifestyle (from a corporate working woman to CEO of your own home), there’s a dress that fits the bill.

This winter, we wanted to highlight dresses for every body, whether you’re petite or tall and no matter what your shape may be. The trick, of course, is choosing wisely.

Sweater Dresses

If a sweater dress conjures images of a sausage casing, it’s time to rethink. Today they come in all different shapes and styles and a myriad of materials. A great winter option, they also deliver unparalleled comfort because knit fabrics allow for stretch and movement. Best advice? Use shapewear to create a smooth foundation, and experiment with accessories and layers to add interest.

If you’re petite: Try a version that hits at or just below the knee in a whisper-weight cashmere knit. For extra elongation, try a turtle neck style paired with tall boots and keep the ensemble monochromatic. Avoid overly bulky details (like cable knits).

If you’re curvy: Try wrap styles and don’t shy away from bold colors and small prints.

If you’ve got a tummy: Top the dress with a long top coat, vest, or duster that hangs open in front.

If you’re big-busted: Go for v-necklines and fit and flare styles that will balance out your proportions.

Nordstrom Holiday Long Sleeve Cable Sweater Dress
Modern Citizen Brea Off-Shoulder Sweater Dress
Faherty Legend Sweater Long Dress
COS Funnel-Neck Wool Midi Sweater Dress
Rails Mila Tie Waist Turtleneck Sweater Dress
REISS Fallon Long Sleeve Turtle Neck Sweater Dress

Wrap Dresses

How do we love a wrap dress, let us count the ways. For starters, it’s universally flattering because the style creates a gorgeous hourglass shape between the v-neckline and the cinch at the waist, both built into the garment. We especially favor patterned versions (floral, plaid), which can add life to winter dressing. If you plan to wear it with tights, get yourself a pretty slip with a lace hem to wear underneath so when it plays peek-a-boo it’s worth the show.

If you have a belly: Choose a wrap dress with more volume and tie the dress higher (at your rib cage) to avoid any tugging at the tummy.

If you’re petite: Beware of too much volume in the skirt. Look for elongating details like vertical weaves and button-up styles.

If you’re big-busted: Give the dress a good test drive in the fitting room to make sure it stays put and, for styles you love that plunge a little extra, consider adding a hook and eye closure at the décolletage.

If you’re arm-phobic: Try styles with balloon sleeves–this is particularly on trend this season. Or, buy a sleeveless version and pair it with a smart jacket (sleeveless=less bulk).

Pink Queen Wrap Sweater Dress
Kiyonna Whimsy Wrap Dress
Topshop Wrap Detail Midi Dress
Donna Morgan Long Sleeve Midi Wrap Dress
Banana Republic Fiori Ruffle Wrap Dress
Equipment Morgan Abstract-Print Wrap Midi Dress

Printed Dresses

Typically long-sleeved and made from heavier materials (wool gabardine, corduroy, flannel), they also feature darker colors and patterns (if it has a black or brown background in the print, proceed). Like their summer counterpart, they’re flowy and not confining, and they can be worn with tall boots, booties, loafers, high-heeled sandals, and even sneakers (only without tights).

If you’re petite: Select a style that has a tie at the waist so you can control some of the volume and create a shape, or add a leather belt from your closet. If choosing a print, opt for a smaller-scale pattern (dainty floral, small polka dots).

If you’ve got a tummy: Wear it without a belt and use a shrunken jacket or shrug to rein in volume with structure while leaving fabric loose over your midsection.

If you’re curvy: Try more tailored styles which provide structure, like a shirtdress. A layered leather bomber is a great complementary element here.

If you’re tall: Have the hem hit you mid-calf to give the fabric a bit of a break.

If you’ve got a big bust: Look for fabrics that give a little, like knits, to keep pulling and gaping at a minimum.

Boden Tiered Jersey Maxi Shirt Dress
Anthropologie Farm Rio Long-Sleeve Shirt Dress
Anthropologie Farm x Anthropologie Printed Maxi Dress
Mille Victoria Dress
Scotch & Soda Long-Sleeved Tiered V-Neck Maxi Dress
Kim Hancher

I am a style consultant and blogger dedicated to helping women 40+ regain their unique style and dress their body type so that they feel confident getting dressed. Hailing from the San Francisco Bay area, I love the color green, anything to do with healthy living, and a great purse.

All products featured on Six to Sunday are independently selected by our editors and contributors. We may get paid commissions on products purchased through our links to retailer sites. However, we recommend products based on our independent research and point of view, and the decisions we make regarding the products we feature on our site are always driven by what we believe our community will love, first and foremost.

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