The cold winter months often have us reaching for our warmest sweaters and bundling up in layers to stay cozy.
However, dressing for winter doesn’t have to mean sacrificing style for comfort.
This season, be bold and make a stylish statement with your winter wardrobe.
With the right attire, you can look and feel your best all winter long.
So grab your favorite winter coat and scarf and get ready to brave the cold in serious style. Let’s get started with 13 show-stopping dressy winter outfits!
Velvet Dress and Boots
Velvet is having a major moment this winter.
For a sophisticated nighttime look, choose a long sleeve velvet dress in a deep shade like forest green, burgundy, or navy.
The plush velvet fabric will keep you cozy while the dark hue and long silhouette is elegant and slimming. Look for a wrap style dress with ruching details for extra flattery and warmth.
Pair with over-the-knee suede boots in black or brown.
The boots elongate the legs while providing insulation from the cold. Accessorize with a sparkling statement necklace and oversized cocktail ring for some added drama.
Finish off with a quilted clutch and faux fur wrap. You’ll look festively chic for any winter soirée or date night.
The luxe velvet and thigh-high boots offer stylish contrast for a dressy yet daring winter outfit. It’s perfect for making a bold entrance at a holiday party or fancy dinner.
Faux Fur Coat and High-Neck LBD
Nothing beats the classic pairing of a Little Black Dress and statement coat.
Choose an LBD in a winter-friendly fabric like sweater knit, ponte, or merino wool.
Opt for long sleeves and a high mock neck to keep you warm and chic. Look for body-skimming silhouettes with subtle details like front seams or asymmetrical hems for modern flair.
Top it off with a plush faux fur coat in a bold color or print.
Faux fur offers drama while keeping you cozy and animal-friendly. Accessorize the monochrome outfit with metallic shoes and bag for a luxe feel. Finish with sparkly hoop earrings and a red lip for timeless sophistication.
This outfit formula is foolproof for any dressy winter occasion, from black-tie galas to birthday dinners.
The high-contrast coat makes a statement and adds warmth while the figure-flattering LBD keeps you looking sleek. It’s an effortlessly chic cold weather combo.
Sweater Dress and Tall Boots
For chic daytime style, you can’t go wrong with a sweater dress and boots.
Choose a sweater dress in soft merino wool, cashmere blend, or chunky knit.
Look for one that hits at least mid-thigh for warmth and coverage. Neutral hues like camel, grey, or oatmeal make versatile wardrobe additions.
Pair it with tall leather or suede boots in black or brown.
The leg-lengthening boots add polish and a touch of edge.
Finish the outfit with a longline wool coat and circle scarf. Carry a structured satchel bag. This outfit works for both casual and dressy winter daytime affairs, from brunch to baby showers.
The sweater dress and boots combination is an effortless way to stay cozy and chic on cold winter
It’s an ideal outfit for running errands or meeting friends when you want to stay warm while still looking put-together.
Faux Leather Leggings and Fur Vest
For a seriously stylish winter outfit, rock a pair of leather leggings with a fur vest.
Faux leather leggings have a edgy vibe while keeping your legs extra warm. Pair them with a chunky oversized sweater in a neutral shade like grey marle.
Top the look with a longline faux fur or shearling vest. This adds a luxe layer while accentuating your waist.
Finish with knee-high boots or booties with block heels for stability on icy terrain. Accessorize with a quilted chain strap bag and felt fedora for a model-off-duty feel.
This outfit is equal parts cozy and cool for winter.
The contrasting textures from the leather leggings to plush fur vest create visual interest. It’s perfect for everyday activities like meeting up with friends or doing casual errands in chilly weather while still looking polished.
Turtleneck Sweater Dress and Tights
A turtleneck sweater dress is a winter wardrobe essential for its stylish comfort.
Choose one in super soft merino wool or cashmere in a neutral solid color like black, navy, tan, or grey.
The turtleneck elongates the neckline while keeping you extra warm. Look for a dress that hits above the knee for easy layering.
Pair it with thick opaque tights and ankle booties or knee-high boots.
Add warmth and flair with a long wool coat and oversized plaid scarf.
Carry a structured top-handle satchel or dome-shaped bag. Finish off with dainty gold jewelry for an effortlessly elegant daytime look.
This outfit formula is fuss-free yet polished for winter.
The figure-skimming sweater dress provides insulation while the neutral color palette offers versatility. Dress it up or down depending on your plans. It works everywhere from the office to day dates.
Faux Fur Jacket and Maxi Skirt
Make a seriously elegant statement in a faux fur coat and maxi skirt.
Choose a longline faux fur coat in a neutral color like taupe or grey. Opt for a subtle shaggy texture instead of long hair for a modern luxe look. Pair it with a fluid jersey maxi skirt in black.
The long length will keep your legs cozy and stylish.
Finish with a mock neck sweater or bodysuit tucked into the maxi skirt. Add suede over-the-knee boots in a neutral tone. Accessorize with a hat and oversized sunglasses for diva-worthy glamour.
Carry a small quilted handbag.
This outfit channels retro Hollywood vibes with its voluminous faux fur coat and flowing maxi skirt.
It’s all about dramatic shapes and textures for high-impact winter style.
The neutral color scheme keeps it modern and chic for day or nighttime wear.
Faux Leather Pants and Funnel Neck Sweater
Give your winter wardrobe an edge with faux leather pants paired with a chunky sweater.
Choose faux leather pants in a dark wash for the look of denim with the insulating properties of leather.
Opt for a straight or wide leg silhouette that’s comfortable while still sleek.
On top, layer a thick funnel neck sweater in a bold primary shade like cobalt blue or cherry red.
The statement sweater adds a fun pop of color. Add cozy warmth with an oversized faux fur collared coat. Finish the rocker chic outfit with heeled ankle boots with chunky lug soles.
This outfit contrasts edgy faux leather with soft knits for a cool winter look. It’s perfect for staying stylish and warm whether you’re heading to dinner with friends or shopping around town.
The bold color sweater makes it festive for the holidays too.
Metallic Midi Skirt and Turtleneck
Make your holiday party entrance unforgettable in a shimmery metallic midi skirt paired with a turtleneck.
A midi skirt is the perfect winter skirt length, hitting below the knee for coverage while still showing some leg.
Look for one with a touch of metallic sheen, like bronze, silver, or gold for instant holiday glam.
On top, layer a black fine gauge turtleneck bodysuit tucked into the high-waisted metallic skirt.
The black turtleneck elongates the torso and anchors the dazzling skirt. Complete the outfit with pointed toe pumps, a glittering minaudière, and elegant drop earrings. A faux fur wrap adds extra glamour.
This holiday party outfit shimmers from head to toe.
The contrast between the muted turtleneck and sparkling skirt makes a stunning style statement. Let the standout metallic skirt be the focal point by keeping the rest of the accessories minimal.
Embellished Sweater and Wide Leg Pants
Stand out with winter whites in an embellished sweater and wide leg pants.
A white sweater feels crisp and fresh for winter.
Choose one with artful beaded or sequined embellishments on the collar or sleeves for festive flair. Opt for a crew neck or mock neck style in a medium weight knit that layers well.
On bottom, pair it with high-waisted white wide leg pants for comfort and polish. Flowy wide leg trousers provide ease of movement while showing off your shoes.
Add heels or black platform booties for a leg-lengthening boost. Finish with a black wool peacoat and bold gold jewelry.
This monochromatic winter white outfit acts as a chic blank slate you can dress up or down. Keep it bright and minimalist for daytime or go dramatic with glittering accessories at night.
However you style it, this look guarantees you’ll stand out from the crowd.
Sweater Cape and Printed Pants
Make sweater weather more exciting by layering an oversized sweater cape over printed pants. Choose a roomy sweater cape that drapes elegantly over your frame for instant warmth and flair.
Opt for a wool, cashmere, or mohair blend in a neutral like camel or oatmeal to get the most wear.
On bottom, pair it with wide leg trousers in a vibrant printed velvet, silk, or satin.
The bold printed pants offer festive contrast under the neutral cape. Finish the outfit with heeled booties and an embellished clutch for dinner or cocktails. Or keep it casual with sneakers and a crossbody bag for daytime.
This outfit combo is easy to dress up or down depending on your plans.
The luxe fabrics and prints feel celebratory for the holidays while the sweater cape keeps you cozy in winter weather. It’s an effortlessly stylish seasonal look.
Shearling Jacket and Matching Mini Skirt Set
Double up on a luxe fabric like shearling by rocking a matching jacket and mini skirt set.
Shearling is a plush wool lining attached to a suede or leather exterior that looks stylish while providing serious warmth. Look for a neutral-toned shearling moto jacket with an oversized silhouette.
Then pair it with a coordinating A-line mini skirt.
On top, add a slim turtleneck sweater in black, white, or beige to balance the voluminous shearling layers. Finish with over-the-knee boots. For extra flair, try a colored hat like red or leopard print.
Carry a small structured bag like a lady baguette.
This coordinated shearling set offers texture, dimension, and coziness ideal for winter. Matching separates in the same luxurious fabric instantly pull an outfit together.
It’s a showstopping look for the colder months.
Satin Slip Skirt and Embellished Sweater
Make a glamorous style statement by pairing a satin slip skirt with an embellished sweater.
Satin has a gorgeous high-shine finish that instantly dresses up any outfit. Look for a bias-cut slip skirt that flatters your frame.
A midi or ankle-length is perfect for staying warm. Choose a rich jewel tone like emerald, ruby red, or sapphire.
On top, layer a crewneck or turtleneck sweater that’s embellished with sequins, beads, or metallic threading.
The ornate sweater offers an opulent contrast to the sleek satin skirt. Finish off the outfit with strappy heels and dazzling chandelier earrings.
Grab a glittering minaudière and swipe on bold lipstick.
This outfit combo is all about striking textures and colors for an elegant winter night out.
The satin skirt billows beautifully as you walk while the embellished sweater catches the light. It’s a showstopping look that’s sure to get you noticed at any holiday party or winter wedding.
Pleated Midi Skirt, Cashmere Sweater and Knee-High Boots
Transition an office or daytime look into evening elegance with the addition of boots. Start with a below-the-knee pleated midi skirt. The modest length is work-friendly while the pleated style adds fluid movement.
Choose one in wool, corduroy, or faux leather.
Pair it with a slim turtleneck sweater or fitted mock neck top.
Opt for soft cashmere in black, navy, ivory, or grey for timeless appeal. Add over-the-knee suede boots in a rich shade like chestnut, dark green, or burgundy.
The boots instantly dress up the look for night while keeping your legs warm. Finish with a quilted chain strap bag.
The pleated midi skirt anchors the outfit while the boots provide a stylish finish. You can also try ankle booties for the office then switch to OTK boots for cocktails or dinner after work.
It’s a versatile winter outfit easily dressed up or down.
This winter, beat the cold weather blues by sprucing up your wardrobe with stylish statement pieces.
By thoughtfully combining dressy and casual pieces, you can take any outfit from day to night.
Finish with elegant accessories like over-the-knee boots, sparkly jewels, and structured bags to tie your whole look together.
