winter dinner outfits

30 Chic and Cozy Winter Dinner Outfits for Every Occasion 

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As the winter months continue to set in, navigating the terrain of appropriate dinner outfits can get pretty overwhelming. From casual weekday quick bites to fancy dinner parties and everything in between, finding the right outfit for your winter events can be a determining factor in feeling good and having a great time with your loved ones. No matter what’s on your calendar, we have got you covered when it comes to your closet. Dive into the 30 winter dinner outfits we’ve put together with you in mind! From attending all of your holiday dinners and enjoying great company in great comfort and style, these outfits might just be what you need to get by this season. 

Cold Weather Dinner Outfit Ideas…

… For a Cozy Dinner Out

1. Wide-leg jeans + blouse + crossbody bag + boots + silver earrings

winter dinner outfits

jeans | blouse | bag | bootie | earrings

These wide leg jeans flaunt an elegant silhouette with a seam detail that works to elongate your figure. Unlike skinny jeans, this more relaxed fit and high waist detail make for an elegant feel and even more flattering fit. The best part? These 90s-inspired blue jeans make for the perfect foundation for a chic and easy outfit to put together. 

While jeans can often serve to dress down an outfit, this truly timeless piece can be styled for (almost) every occasion. Pair with this delicate top for a feminine touch and effortlessly balance the relaxed vibe of the denim with an elevated, charming piece. 

A small bag is essential for any dinner outing, and this look wouldn’t be complete without this particular choice. This crossbody bag can be carried both through the longer or shorter strap, on top of being the ideal size to hold all of your valuables throughout the night. Its elongated shape and curved edges work to simultaneously soften the look and maintain its sophisticated flair.

Matching the seam detailing from the jeans, these booties are the perfect shoe for this “laid-back” but ever-so-elegant look. With a block heel and square toe, these ankle boots also feature modern elements that effortlessly blend the contemporary and the classic. 

For the final piece, add these beautiful sterling silver earrings as an extra charming detail. 

2. tie belt jacket + draped pants + studded buckle shoes + bag

winter dinner outfits

jacket | pants | shoes | bag

Who ever said cozy can’t mean chic?! This outfit turns a last-minute dinner out into an occasion with comfortable pieces and fashion-forward style. A beautiful jacket starts off the look; use the tie detail to cinch in your waist and give structure to your overall look. 

When it comes to casual-chic fashion, drape pants are a fool-proof alternative. Comfortable, flattering, and easy to style, these staple wardrobe pieces will always have your back. Keeping your main components relatively monochrome is a great choice if you’re looking to keep your outfit simple and sophisticated. 

For this look, our accessories bring in the fun and edge. These buckle shoes are ideal for their classic silhouette, while their studded details balance an otherwise timeless outfit with a subtle contemporary touch. Bring it all together with this textured bag that brings together the color palette of your outfit! 

3. low-slung wide-leg pant+ + cashmere sweater + wool coat + sneakers + shoulder bag

winter dinner outfits

pants | sweater | coat | sneakers | bag

For braving the cold, enjoying your dinner, and staying on top of your fashion game. We all love layering during the colder months of the year, and that statement couldn’t be more true than when a big wool coat is involved in the mix. 

As another take on the monochrome look, this outfit features the most comfortable pieces ever for a truly warm and cozy outing. The cashmere crew sweater and wide-leg pant keeps the silhouette straight and boxy, making for an oversized, laid-back feel.

A wool blend overcoat solidifies the chic element of the composition, while both the Sambas and the handbag work to bring balance and elegantly accessorize the final ensemble. 

Want to know the best way to balance casual and elegant styles? I created a free printable for you that you can get by signing up here!

4. wool topcoat + turtleneck + pants + loafers + handbag + hoop earrings

winter dinner outfits

coat | top | pants | shoes | bag | earrings

If you’re weary about mixing these two classic colors, we have a few tricks to get you going! Black and brown can be overwhelming to style for the first few times, but focusing on similar tones makes the process that much easier to navigate. For this outfit, focusing on deep brown shades and a true black allows us to find cohesive pieces that come together in an elegant look for any night of the week. 

Start with the basics! A simple, fitted black turtleneck and straight pants make for a sleek base, while the wool topcoat takes the spotlight with its sweeping style. Finish things off with this beautiful pair of loafers that blend together all of the colors, while also bringing in some gold hardware detailing to go with a delicate pair of small gold hoops.

This staple brown bag is the cherry on top, with a beautiful elongated structure that keeps things interesting and functional. 

5. wool pants + turtleneck sweater + oval earrings + ankle-high leather boots

winter dinner outfits

pants | sweater | earrings | boots

Truly simple outfits can be some of the greatest hits when done right – it’s all about finding those few perfect pieces and bringing them together. Pair these beautiful Italian wool pants with a turtleneck sweater for an already perfect start.

Leather ankle boots bring in texture to the look, also working to diversify the color palette and feel of the outfit. For this look, less is more. Add in a pair of beautiful oval earrings for a romantic accessory that continues to bring harmony and elegance to your fashion choices. 

6. fringe knit top + corduroy pants + mary jane flats + shoulder bag

winter dinner outfits

top | pants | shoes | bag

Including a couple of fun elements when creating a simple look for a relaxed dinner makes all the difference. Something as simple as detailing on a sweater or a handbag can easily bring together your outfit and your confidence for the best time with your loved ones – and this fringe knit top is the perfect example. 

The material keeps this piece weather-appropriate and comfortable, while the corduroy pants also keep you warm and feature a flattering fit. 

Even out the light colors from the clothing with some timeless, black accessories. This simple quilted bag accessorized the look perfectly, while these Mary Jane flats bring in a dash of preppy, chic charm. 

7. straight pants + cashmere crew sweater + clutch + horsebit sandal + herringbone necklace

winter dinner outfits

pants | sweater | clutch | sandals | necklace

You know how truly timeless outfits make us feel – and this is one of them. This simple, understated, yet ultra-elegant combination is everything we love about classic style. Elegant, cohesive, and clean, these looks will always be the ideal choice for a night out – wherever it is you’re going.

These straight pants make for the perfect base with a beautiful neutral tone, while a camel cashmere sweater brings in some color. For an eye-catching accent detail, the deep brown sandal and clutch do the trick, polishing off the entire outfit with class.

A herringbone necklace adds the ultimate final touch, tying together the gold hardware detailing from the shoe and balancing the look on top. 

8. rib-knit dress + oversized coated jacket + sheer tights + chelsea boot + headband

winter dinner outfits

dress | jacket | tights | boots | headband

When you’re crunched for time – and, let’s be honest, even when you’re not – an all-black outfit can be the easiest way to get it right. The original monochrome shade has won us over many times before, which is why we always come back. 

This rib-knit little black dress starts things off, featuring a twist detail on the back that’s perfect for when you get warmed up. The oversized faux leather jacket is the real star, giving this otherwise classic look a relaxed and modern twist.

Pair with black tights and ankle boots for warmth and comfort, and a beautiful detailed headband for the much-needed sparkle of a charming finishing touch.

9. faux leather pants + sleeveless cashmere sweater + slingbacks + flap chain bag + hinge bracelet

winter dinner outfits

pants | sweater | shoes | bag | bracelet

We meant what we said: cozy and elegant do go together, and all-black is a no-miss game. These faux leather pants bring an immediate heightened feel to this otherwise very simple outfit. 

While getting monochrome right isn’t hard, getting it perfect is a matter of finding the perfect fit. This sleeveless cashmere sweater is beautifully designed to cinch in and out at all of the right places, resulting in a top that looks like it has been made for you. 

For accessories, keep it simple with a small black bag, classic slingbacks, and a gold wide bracelet that seamlessly connects it all.  

… For a Casual Bite

10. draped pants + half-zip sweater + fitted tee + ballet flats + metallic ball earrings

winter dinner outfits

pants | sweater | tee | shoes | earrings

If you’re being whisked away on a last-minute dinner with friends or even a casual date, this outfit has you covered. The delicate balance of casual and chic makes this combination perfect for a number of fun occasions, starting with these striped draped pants that feature a flowy, very elegant fit as it falls. 

This half-zip merges the structure of a classic sweater while also throwing in a more relaxed feel. For a heightened casual look, try tucking in the edge of your sweater for more interesting layers and better composition. 

Pro tip: If your sweater isn’t fitted, wearing a simple white tee underneath makes for a charming and truly elevated detail. Give it a try! Feel extra comfortable and chic as your tee gives off the elegant touch we know and love. 

Finish off with a simple but always effective pair of ballet flats and some silver earrings. 

11. wool coat + wide-leg jeans + sweater + loafers + jade earrings

winter dinner outfits

coat | jeans | pullover | shoes | earrings

We’ve said it before and we’ll say it again! The right pieces can take a simple outfit and make it some of the best – it’s all about finding the perfect fit and playing around with proportions. 

For this outfit, take the simple concept of jeans and a sweater. This slim wide-leg denim piece is just right, falling perfectly with the funnel-neck pullover that effortlessly brings in a touch of elegance. Bring it all together with a beautiful green woolen coat, making sure to wear it open to expose all of your gorgeous layers. If you need to brave the cold and button-up, the belt allows you to cinch in your waist for the perfect look either way.

A pair of stunning earrings bring in a chic air of fun, while loafers keep the outfit grounded and you ready for anything. 

12. straight jeans + ruffle-neck sweater + rib-knit scarf + ankle-high sock boots + shoulder bag + twisted hoop earrings

winter dinner outfits

jeans | sweater | scarf | boots | bag | earrings

With delicate details to these classic pieces, this outfit goes to show just how many variations there are when it comes to putting together a classic-casual vibe.

Pair these 90s straight jeans with this gray Merino sweater – both the asymmetrical buttons in the denim and the ruffle neckline of the top bring a more modern flair to an otherwise timeless combination. 

Dress this outfit down slightly by throwing on a simple black scarf on top, a structured shoulder bag, and a pair of simple twisted silver earrings. Round everything out with these beautiful ankle-high sock boots for a little bit of height and a little bit (more) of chic! 

13. jeans + boots + cashmere sweater + shoulder bag + hoop earrings

winter dinner outfits

jeans | boots | sweater | bag | earrings

These jeans set the scene for this outfit with the right proportions: super high-rise pants that are slightly shorter on the bottom – which means it’s perfect for showing off your shoes! 

These gorgeous brown boots complement the color of the jeans and determine the overall direction of the look. By adding height and a heavy component to the bottom, this shoe choice calls for a simple yet cohesive piece at the top. This cashmere sweater brings in the color of our main piece while also softening the look with its classic silhouette. 

Small gold earrings bring in a fun, elegant element and this beautiful shoulder bag tops it off with a hint of beautiful color for balance and an added sprinkle of your personal style. 

14. straight jeans + faux shearling-lined jacket + turtleneck + shoulder bag + ballet mules

winter dinner outfits

jeans | jacket | turtleneck | bag | shoes

Focusing on a neutral color – or colors – is a great way of ensuring your outfit stays elegant – and gives us the opportunity to land the interest of the look in the design of the pieces themselves. 

Beautiful straight jeans and a turtleneck compose the base of this already-stunning look. Here, this faux shearling-lined jacket is the main event – if the weather permits, wear it open for a more casual and laid-back moment. The blended textures of the base pieces, the neck detailing and the leather in this oversized piece are just what we want! 

Use this beautiful shoulder bag to bring together the different cream tones throughout the look, and these modern ballet mules for balance and yet another bulls-eye hit of classic modern style. 

15. leather blazer + knitted miniskirt + monk strap shoes + sheer tights + fine-knit turtleneck sweater

winter dinner outfits

blazer | miniskirt | shoes | tights | sweater

This is another great example of how you can take all of your favorite closet staples and earn your spot on the best-dressed list for your casual dinner! 

Start with a classic knit turtleneck sweater – when it comes to true closet must-haves, this piece will always make the list. Pair with this mini skirt on top for some great texture and balance.

Black tights and some elegant chunky shoes finish off the perfect foundation for your upgraded casual bite look. Feel free to stop there and accessorize, or switch it up with our preferred main piece. This big leather blazer fights off the cold and brings in a few beautiful textures to your outfit. Wear it open to show off your layers! 

… For a Glam Dinner 

16. knitted dress + shoulder bag + mules + drop earrings

winter dinner outfits

dress | bag | mules | earrings

Of course, we could never get through winter date outfits without shouting out our favorite sweater dresses. A beautiful dress can make us look more put-together than ever while cutting our efforts in half when the time comes to get ready – which is why we love building outfits around them!

This open-back knitted dress is ideal for every glamorous dinner you have to attend for the season, keeping you ultra comfortable and warm while making no sacrifices on the style front.

When it comes to styling, bold black accent pieces are the perfect way to dress up this look with a few simple touches. A small black shoulder bag balances out the delicate mules, while these statement earrings make for the perfect final piece. 

17. ribbed midi dress + metallic leather shoes + crystal clutch bag + orb earrings

winter dinner outfits

dress | shoes | bag | earrings

If you love the low-maintenance of a dress but tend to go towards darker colors, this look might be the one you’ve been waiting for. 

This classic black turtleneck midi dress hugs your figure in all of the right spots, making you look and feel your best as you chat away throughout the night. 

For a fun end-of-the-year touch, try adding a few metallic pieces to your final ensemble. These leather Mary Jane-inspired shoes are ideal for bringing a different element to a well-loved basic, while still maintaining a chic and elevated feel to the whole outfit.

To go with it, opt for a simple but interesting pair of silver earrings and, of course, a small crystal clutch bag as a way to add some sparkle without overwhelming the look at all. 

18. pleated metallic top + mini slip skirt + earrings + pumps

winter dinner outfits

top | skirt | earrings | pumps

This gorgeous pleated metallic top makes this look! This stunning silhouette values your collarbone area while the subtle cinched detail at the waist ensures that you get the flattering fit we are all always after.

Since we want to keep the attention on top, pair this top with an elegant midi slip skirt. The slight sheen of the skirt will complement the fabric and feel of the top, without overwhelming it in any way. Finish off with a simple black pump for the ultimate chic choice. 

For accessories, keep it simple but fun with these small two-toned earrings that bring in the different color aspects of our beautiful top. 

19. satin wrap dress + jewel-heel shoes + earrings + ring

winter dinner outfits

dress | shoes | earrings | ring

It’s a “yes” for silver accessories that complement the shoes without overpowering them.

When it comes to getting the fit right, wrap dresses have a way of ranking high. This versatile look in dark green makes dressing for a fancy dinner easy – its beautiful satin fabric brings in an already-elevated feel, while the buckle detailing ensures a perfect cinch at the waist for structure.

Finish off with some beautiful classic pumps, and match a couple of simple yet impactful pieces of jewelry for a full-circle dinner fit.  

20. metallic pleated skirt + cashmere top + ankle-detail heels + pleated clutch

winter dinner outfits

skirt | top | shoes | clutch

Dress up in comfortable glamour with this metallic pleated skirt that steals the show. Simple in structure and designed with beautiful eye-catching fabric, this piece is way easier to style than it may seem.

Pair with this sleeveless cashmere top for equal doses of elegance and comfort, as the turtleneck detailing elongated your silhouette. For accessories, opt for a black pleated clutch for a subtle match, and anklet-detail heels for some added flair and the ideal final touch.

… For a Romantic Date Night

21. mid-rise straight jeans + square-toe slingback flats + button-up shirt + pearl headband

winter dinner outfits

jeans | shoes | top | headband

Romance can manifest in many different ways when it comes to outfits. Starting off with our dinner date looks, this oh-so-classic look might just make its way into your year-round dinner outfit rotation. 

Begin with some straight dark jeans, making sure that they’re the right fit. On top, add this button-up shirt – with a cardigan look to it, this top immediately screams elegance while also balancing a romantic, lightweight feel with its sheer fabric and jewel-button detail. 

Add the final romantic touches with these mesh slingbacks that were made for date night! The pearl headband polishes off all of the delicate details of the outfit for a perfect evening – whether you’re getting dressed for a first date or the 100th, you’ll get it just right with this look. 

22. knee-high boots + sweater dress + buckle belt + hoop drop earrings

winter dinner outfits

boots | dress | belt | earrings

If you feel like stepping it up for date night, this gorgeous dress is the way to do it. Simple in structure and intricate in design, this sweater dress pretty much does all of the styling for you (make sure to pick out your most comfortable, nude slip dress to wear underneath!) 

Pair with some simple gold earrings and a knee-high brown boot to balance the delicate fabric of our main component. Pair with a brown belt to cinch in the waist even more and add a little something extra, or pass on the accessory to keep it super clean and ultra-feminine. 

23. tweed miniskirt + shirt with ruffle detail + ballet flat + sheer ankle socks + flap bag + hoop earrings

winter dinner outfits

miniskirt | top | shoes | socks | bag | earrings

Yet another classic take on a date night outfit that you won’t want to miss. This shirt steals the spotlight, with its beautiful ruffle detailing shining front and center of this winter dinner look.

A simple tweed miniskirt balances out the more conservative top, while sheer black ankle socks and ballet flats add a modern take on a classic shoe & sock combination. 

To finish things off, add a small black bag with gold hardware, and pull those details together in delicate gold earrings. 

24. draped pants + off the shoulder top + slingback pumps + clutch

winter dinner outfits

pants | top | shoes | clutch

A special romantic night wouldn’t be complete without the perfect winter date night outfit.

Start your look with these beautiful draped pants for a flowy, elegant feel. This off-the-shoulder top flatters your collarbone area while also balancing your beautiful black and white ensemble, also keeping you warm in the process. 

To bring it to the next level, accessorize your look with this pair of stunning slingback gold pumps that contribute an air of sophistication and undeniable style flair to your final look. A gold clutch tops everything off perfectly, working to both emphasize the shoe and elevate the elegance of your look. 

25. striped polo-neck sweater + faux-leather miniskirt + tall boot + sheer tights + hair clips

winter dinner outfits

sweater | miniskirt | boots | tights | hair clips

For this look, the classic comes together with the help of some subtle, contemporary elements. This striped polo-neck sweater kicks things off with a warm and classic feel, and the faux leather mini skirt brings on the perfect proportions; tuck the sweater slightly inside your skirt for a better overall fit. 

To complete your look, add a pair of sheer black tights and knee-high flat boots. Include these open-shape, gold hair clips for some less traditional (but just as fun!) final touch – who doesn’t love a hair accessory?

26. herringbone coat + ribbed dress + bucket bag + knee-high boot

winter dinner outfits

coat | dress | bag | boots

Go for unparalleled sophistication in this outfit – and we’re not sure you’ll ever want to take it off.

This gorgeous dress fits beautifully with its wrap detail at the waist, and its neckline works to balance out the rest of this otherwise modest look. 

Pair with black knee-high boots and a small black bag that brings cohesion to your beautiful date night fit; the boot’s pointed tips and the bag’s more modern design make for the perfect blend of contemporary elegance. 

27. ribbed dress + knee-high boot + mini shoulder bag

winter dinner outfits

dress | boots | bag

Truly simple, chic, and fun. Steer away from blacks and grays and enter a new arena of stunning classic neutrals for your date night look. 

This ribbed dress sets the scene, making for a comfortable and naturally elevated look through its length, neckline, and ribbed detailing.

When it comes to shoes, the croc-embossed boots bring some elegant edge through their texture and light color that balances perfectly with the warm tone of the dress. 

For a perfect accessory, this mini shoulder bag contributes a subtle and still-beyond-elegant accent color while bringing some diversity to this quintessential outfit. 

28. smocked button-up shirt + leather belt + wide-leg tuxedo pants + mule

winter dinner outfits

top | belt | pants | mules

Another all-black ensemble for the books, and we have zero regrets. Whether you are getting dressed for dinner earlier in the day or right before you head out the door, this outfit works every time when it comes to making a lasting impression. 

This short-sleeved button-up shirt brings gorgeous texture and class to your dinner date, pairing perfectly with a messy ponytail that allows you to show off that collar. 

Wear it with black pleated tuxedo pants made from luxurious fabric, bringing weight to the final look without stealing the moment from your top.

For accessories, a belt helps you cinch in at the waist and break up your monochrome outfit, while simple gold hoops are the only jewelry you need.

Finish off with a pair of stunning mules with a block heel that contributes to your look just as much as it does to your confidence!

29. ribbed midi skirt + turtleneck long-sleeve tee + knee-high boots + leather belt + puffy hoop earrings

winter dinner outfits

skirt | top | boots | belt | earrings

In our opinion, dressing to impress isn’t ever quite as comfortable and chic as it is during the winter, and this outfit proves our point. 

This cream ribbed midi skirt is the main piece for this composition with its great texture, quality material, and stunning aesthetic. A beautiful turtleneck with long sleeves complements the skirt and allows it its time to shine, and both are brought together by a leather belt that effortlessly softens the transition in the look. 

A knee-high brown boot continues to complement the brown accents and small silver earrings tie together with the subtle hardware on the belt. 

30. striped pleated skirt + ribbed long-sleeve t-shirt + knee-high boot + bag with feathers

winter dinner outfits

skirt | top | boots | bag

If you’re after some more modern elements in a classic outfit, all you have to do is pick out a couple of your favorite pieces to work around!

In a similar composition to our last date night fit, we are beginning this look with a pleated midi skirt. Unlike the other looks, this skirt switched things up with a slight geometric design that leans more towards a contemporary feel while still maintaining classic elements like its length, shape, and texture.

Continue to balance this detail out in the rest of your outfit with a classic knee-high black boot and a simple long-sleeve top. 

To finish it off with a dash of fun, romantic edge, include this feather handbag in your final look! 

Finding Your Perfect Winter Dinner Outfit Is Easier Than Ever

From classic combinations to sculptural accessories, we included it all. We hope these winter outfit ideas can get you through the many fun, cozy, glamorous, and casual winter dinners we know this time of year holds for you. We’ll see you for your next date! 

Looking for more winter outfit ideas? These Dark Academia outfits are classic, moody, mysterious, and perfect for this cooler season.


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.