Dresses may not be at the top of your outfit menu this time of year, especially the year we’ve been having, but there are some mid-season dress trends for winter that offer a chance to refresh your wardrobe and maybe even your outlook. Who can resist the call from cozy knits and the velvet fabrics of cold-weather frocks? Those are just two dress trends we’ll break down below.
First up, the classic sweater dress. Whether you’re outfitting for the office, a cozy dinner, or Saturday shopping, if you haven’t already, it’s not too late to embrace sweater weather in dress form. For a more casual look, check out Gap Factory’s CashSoft Relaxed Crewneck Sweater Mini Dress in taupe or navy. This is a blank canvas of a dress and can be worn on its own around the house with fuzzy socks and slippers or layered with leggings and hiking boots for a quick coffee run. For something with a bit more structure, there’s the same brand’s CashSoft Ribbed Mockneck Midi Dress. This is more formal and form-fitting in shades of burgundy, beige, and black. Wear with a blazer and heeled boots for work, or with a cardigan and clogs for a chill date night. If you’re looking to experiment with your sweater dress game, consider a cardigan-style knit dress. Nordstrom Rack has a Rib Knit Cardigan Midi Dress in soft grey or classic navy. Wear it on its own or open it up and wear it as a duster with jeans and a turtleneck.
And speaking of turtlenecks, another dress style to explore this mid-winter into early-spring is high-neck dresses. From turtlenecks and mock necks to cowl necks and boatnecks, frocks with higher necklines provide great coverage during the transitional season. And while they are a bit reserved, they can come across as chic and flirty. Combine this trend with a sweater dress, and you’ll have another great option from Nordstrom Rack with their Tie Waist Fit & Flare Sweater Dress in a wide range of colors. This knit number has a mock neck, a tie waist, and a flared pleated skirt, and definitely hits on the flirty side of this trend. For a chic factor, there’s Target’s A New Day Long Sleeve Midi Dress in black, black floral, or olive green. This frock features an easy pullover design with a mock turtleneck and a side slit for easy movement. Accessorize this with gold earrings and a statement bangle, preferably also gold.
Another chic dress trend is velvet dresses. When it comes to winter fabrics, velvet is the undisputed favorite. You may feel velvet is more of a holiday material, but when rendered in an unexpected silhouette, it can feel quite fresh come March. Loft’s Velvet Ruched Midi Dress in black with a red floral motif feels very slinky and cool with the ruched detail, long sleeves, and front slit. Wear it with tall black boots and a utility jacket for a mix-match of femininity and function. For a more earthy, boho style, there’s Baltic Born’s Veronica Velvet Maxi Dress in a rust, dark sage, or espresso. This romantic frock features a floral burnt effect with fluttery sleeves, a v-neckline, and a smocked waist with stretch. If you’re feeling a bit fanciful, feel free to wear it as you dive into your latest winter read, or take it on the town with a wool coat and cowboy boots.
If your tastes run more toward the preppy than the bohemian, well, you’re in luck because there are lots of plaid dresses on offer. You may feel tartan is strictly a fall and holiday print, but there’s plaid for all seasons. For winter, that plaid should be edgy in deep color combos; leave the gingham for the warmer months. You can also wear plaids in unexpected silhouettes for winter. Sure, there’s the classic shirtdress, as Kiel James Patrick’s Apple Cinnamon Flannel Maxi dress with a matching belt for a seamless outfit. However, I’m liking the silhouettes from Boden, like their Check Long Sleeve Maxi Dress with a button half placket, empire waistline, and buttoned cuffs. Or, the Eda Check Shift Dress with piping, structured fabric, and a statement collar. For plaid dresses in general, this season, look for unexpected silhouettes, either in stores or in your own closet.
And speaking of unexpected silhouettes, lastly, we have the blazer dress. Full disclosure: this style is not for the faint of heart or anyone triggered by ’80s trends. Yes, a blazer dress can bring to mind the bold shoulders and hard lines of 1980s power dressing, but with some subtle shifts, it’s been brought into the modern day. Dillard’s Scuba Crepe Long Sleeve Blazer Pleated Fit and Flare dress features a faux wrap waistline, notched collar neckline, and is available in a shade of rhododendron, creating both a contemporary and classic outfit when worn with black tights and pumps. Another classic to check out is Ann Taylor’s Double Breasted Blazer Dress in pine, which can be worn as a stand-alone dress or worn open for an avant-garde take on the oversized blazer with a button-up and trousers.
Sweater dresses, velvet dresses, plaid dresses, and unexpected silhouettes are all up for grabs as we continue to journey along with the season. You probably already have versions of these dress trends in your closet, so why not take this as a sign to “dress up” and take on the rest of this winter with style?


