It’s cold, it’s dreary and it’s hard to get inspired to get dressed some mornings in the thick of winter.
Finding a look that is as warm as it is cute is no lay up. But there is actually nothing easier than throwing on a long-sleeved comfy dress for your workday wardrobe. Just add a pair of your favorite opaque tights -- in black, brown, tan, or a jazzy color-- your favorite boots, and insta-presto, you are READY!
We found 16 great dresses to solve your winter “What to wear to work?” quandaries. Or to wear for drinks, or brunch or casual date night for that matter. Consider your winter dressing problem, SOLVED!
Best part? All these dresses are priced at $100 and under! Your OOTD is a snap!
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This vibrant, paisley-print dress is as effortless as it is adorable. While it looks like a mini, it wears longer. It gets bonus points for comfort, since it's made of a cozy, stretchy knit. Style Hint: Throw a cardigan over it for work, or a suede moto jacket for date night, since it has an open-back keyhole.
The basic sweater dress gets a big upgrade with an elegant midi-length hem and a vertical ribbed texture, both of which add slimming lines to any wearer. Style Hint: This body-conscious silhouette is a perfect layer for your favorite embellished jacket, so add a blazer, belt and any other accessories that need a plain background underneath. We'd reach for a trendy shearling with a moto cut to bring this basic into 2019.
Faux fur cuffs transform this simple black sheath into a luxurious dress. The sleeves are ¾ length which makes it even chic-er in a Jackie O kind of way, and keeps the fur out of the way when you’re working or at dinner. Style Hint: Pair with ladylike heels or grown up Mary Janes, and add a sparkly necklace for extra date-night drama.
This asymmetrical hemmed design in a chiffon fabric looks pulled together with a simple black belt. It's lined and long, so while you look like you're in a flowing print cloud, this dress is perfect for winter functions. Style Hint: Wear with black boots and if the neckline is a little low for your office, layer a sleek black turtleneck underneath. It will offer coverage without distracting from the print of the dress.
We love this dress by Universal Standard in collaboration with J. Crew, for its bright berry color and sumptuous cashmere. But above all, we love it because it's available in sizes small through 5X (XXXXXL). Style Hint: Wear with or without tights, and throw on a pair of black flat over-the-knee boots on for an adorably mod 1960's look.
The most flattering dress to slip on, any day of the week, is what's called fit and flare because it fits from the neckline to waist and then flares into a gentle A-line from there to the hem. We love the gentle bell sleeves with elastic around the wrists -- the best of both worlds since some oversized sleeve draping can get in the way when we're working! Style Hint: The keyhole neck is a flattering detail: Wear your hair up to accentuate the tie-neck, and no other accessories are required!
Nothing makes us fall in love with a dress instantly more than pockets! This one, in faux suede material and a chic ochre color is perfect as a diversion from all our winter black and grey tones. We’re sold, all for under $30. Style Hint: Try brown or hunter green tights with this color because black looks a little bumblebee, and wear brown suede boots to keep the earth tones going.
This oatmeal cable-knit dress is cozy, chic and ultra-flattering with an oversized cut and gently undulating texture. Style Hint: If this shape overwhelms your frame, defining your waist with a wide belt is a great solution. We'd reach for a faux snakeskin one, as we love mixing textures. Add boots or sneakers and you’re good to go.
This button front, tie-waist dress will be your go-to office outfit because of its menswear-inspired check in a comfortable cut with built-in belt. Style Hint: Throw on a pair of opaque black tights and black ankle booties and your legs will look miles long.
Get into the Cowgirl trend with this western-inspired floral midi. We love that the olive cherry blossom print works for any season. Style Hint: Pair it with cowgirl boots, but try some of the shorter ones with tights that pick up any of the colors of the print.
Don't shy away from this bright red bold, since it actually flatters most complexions beautifully and adds a touch of pop to your winter wardrobe. Style Hint: A long overcoat will highlight the short hemline of this red mini, so never worry that your coat is longer than your dress, since contrasting hems looks confident. Add some black tights and slouchy boots and your outfit is complete.
This ultra-feminine, breezy dress is made even better because Treasure & Bond have vowed to donate 2.5% of net sales to youth-empowering organizations. Style Hint: Add a leather belt to cinch the waist like in the picture: this creates the illusion of much longer legs. Match your belt with your boots, even lace-up hiking style boots like these, since it goes with the chic country vibe.
This candy-striped midi looks as comfortable as it does delicious. Hidden internal buttons mean that despite the wrap feature, you won't find yourself caught in any embarrassing wardrobe malfunctions. Style Hint: Match your shoes to your favorite color stripe and you're made in the shade. For a jacket, camel suede or leather adds a little fun texture.
Your winter wardrobe needs a few unexpected pieces like this bright, poppy floral. We love the layered gauzy fabric and skater style skirt, criss cross neck and sheer sleeves. Style Hint: Pick up the skater vibe with white booties as shown. Throw on a pair of nude tights to keep this look cohesive yet cozy.
Wear it just like Something Navy founder and blogger Arielle Charnas does here with heeled black suede booties for an effortlessly chic look.
