classy winter dresses outfits

Dress Your Best in These 16 Classy Winter Dresses Outfits

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It’s about this time each year that I start to feel like I’m in a slump with my wardrobe. The holidays are over, winter is in full swing, and some days it feels so much easier to reach for the same pieces again and again. However, just because we’re in between holidays and it may be gray outside doesn’t mean you can’t shine in a fun outfit and feel classy and confident – no matter if there’s a special occasion or not!

Read on below for 16 classy winter dresses outfits that will add a bit of glamour to your cold-weather looks. They’re perfect for a date night, a trip to the theater, drinks with the girls, or maybe even a candlelit dinner at home!

1. Emerald Green Slip Dress

classy winter dresses outfits

dress | coat | shoes | earrings

Jewel tones are the perfect look for winter months, and this emerald green number delivers. The longer length of this dress is perfect for cold weather, and a classic appearance.

Plus, it’s easy to use as a layering piece – if you’d like to add sleeves, wear a black or white turtleneck underneath. Or, pull out one of your chunky sweaters to wear on top, which will give this dress new life as a long skirt. This is also a way to give this dress a more casual appearance.

Though this dress doesn’t have sleeves, it’s the perfect opportunity to throw on an elegant overcoat to complete the look. As for jewelry, a simple pair of linked interlocking gold hoops make the perfect statement. Add a pair of slingback kitten heels with a closed toe for the finishing touch.

2. Monochrome Look in White

classy winter dresses outfits

dress | faux fur coat | heels | earrings

A monochrome look is one of the easiest ways to look put together and elevated. This dress in winter white features a classic silhouette and long sleeves that are perfect for cold days. The “cold shoulder” is the perfect flirty touch to the elegant look.

Go all in on the sophisticated, vintage-inspired fit by adding a faux fur coat. If you’re following the latest trend (old money looks, anyone?) you’ll fit right in with this pairing. Cap-toed slingback heels in white, with elegant gold and pearl earrings will complete the look.

3. Classic Little Black Dress

classy winter dresses outfits

dress | camel overcoat | two-toned ballet flats | pearl earrings

This midi skirt-length number is the perfect modest take on the little black dress. If you prefer a little more coverage than the typical mini dress, this is a great choice. This is another dress that features a classic silhouette. It tucks in slightly at the waist, offering a flattering fit for many body types. The high neckline offers more coverage as well, making it a great option to reach for when it comes to occasions that might call for a more modest look.

Cap-toed ballet flats and pearls are timeless accessories that will complement the style of this dress. This is a look that exudes the same kind of elegance that is reminiscent of many of Audrey Hepburn’s looks – just proving once again that this kind of look never goes out of style. A belted camel overcoat completes the outfit.

4. Long-Sleeved Satin Dress

classy winter dresses outfits

dress | silver heels | crystal earrings

This long-sleeve dress will be sure to turn heads when you’re going out! If you love minimal designs that pack a punch, this stunning piece is perfect for you. The bell sleeves offer a vintage flair, while the flowing, satin material would be the perfect choice for a night on the dance floor. This dress would also be a very comfortable choice with its looser fit – one that you won’t be dying to switch for pajamas at the end of the night.

Silver shoes are the perfect way to complement this dress without competing with it. Add a pair of crystal earrings, and you complete one of the most fun classy winter dresses outfits.

5. Romantic Red Dress

classy winter dresses outfits

dress | shoes | heart earrings

What better month to rock a red dress than February? This number is part of a more romantic take on classy winter dresses outfits. It’s also one of the more casual winter dresses on our list.

And even if it’s not Valentine’s Day, you can pay homage to the month of love by adding a pair of gold heart earrings. If you prefer a slightly lower neckline, this v-neck look is very flattering without being too revealing. Add a pair of nude block heels with an ankle strap for a comfortable fit.

6. Floral Statement Dress

classy winter dresses outfits

dress | tights | slingback heels | earrings

There’s just something about this dress that screams classic, elevated sophistication. Maybe it’s the fact that it’s essentially the Chanel packaging in dress form, from the floral appliques to the black-and-white color scheme! Either way, if you like to rock a mini dress, this is a unique, stunning way to do it.

To add a bit of coverage (and warmth for a cold winter day), add a pair of tights. You could choose a pair with a bit of sheerness to them, or a more opaque pair for a more modest appearance.

If your climate is especially cold, you might even consider purchasing a pair of fleece-lined leggings that offer the appearance of sheer tights. Slingback heels with a pointed toe help to lengthen the appearance of your legs for a flattering effect. Lastly, crystal and pearl statement earrings are the perfect finishing touch.

7. Satin Wrap-Style Dress

classy winter dresses outfits

dress | kitten heels | coat | bracelet

Speaking of color, try this style in a beautiful shade of burnt umber. This is perfect for those who like to wear warm colors. The satin material of this dress makes for a comfortable fit, with a flattering, elegant silhouette where the bow is tied around the waist. It would also easily blend into the category of fall dresses, making it one that would make for a great transitional piece between seasons.

Next, add a pair of burgundy heels if you want to continue the colorful look in your shoes. A kitten heel is a good idea when it comes to winter dressing, as the winter weather is often not conducive to wearing tall heels. Plus, a closed-toe shoe will keep you warmer than open-toed in colder climates. Complete the outfit with a long coat, and a gold bangle bracelet.

8. Blazer Dress

classy winter dresses outfits

blazer dress | knee-high boots | tights | earrings

If traditional dresses aren’t your style, a blazer dress is a great option for you. The blazer dress offers a fun, masculine edge to your classy winter dresses outfits. This structured piece is a unique take on workwear that is perfect for a night out, or maybe dinner with friends.

While a pair of tights and classic black pumps would look great with this dress, if you prefer a little bit more coverage since this is technically a mini dress, try knee-high boots. This pair of shiny leather boots adds a new texture to the monochrome look. Simple silver stud earrings finish the outfit and tie in the silver detail on the dress.

9. Button-Down Shirt Dress

classy winter dresses outfits

shirt dress | long coat | bag | croc-embossed leather boots

Speaking of workwear-inspired fits, here’s one dress that could take you from your day at the office to a date night out. This shirt dress is elevated with a draping effect at the waist, which also provides a flattering fit around your midsection.

A structured, long coat is the perfect layer to add to further add to the sophisticated look. Add a patent leather bag and croc-embossed ankle boots to introduce a few more textures to the look. And if you need a little extra warmth, a pair of tights will do the trick.

10. Fringe Dress

classy winter dresses outfits

fringe dress | ballet flats | earrings

Have a little fun with your little black dress by choosing one with fringe. This is the perfect piece if you’re looking to try out the jazz aesthetic this year. Layers of fringe like this call to mind the flapper era!

Keep the attention on your statement dress with simple accessories, like this pair of black ballet slipper flats and a pair of dangly silver earrings.

11. Ribbed Sweater Dress

classy winter dresses outfits

dress | trench coat | shoulder bag | leopard flats | neck scarf

The lover of sweater weather will love this cream ribbed sweater dress. This dress features long sleeves and a cozy fabric, and it’s casual enough to wear for a number of different occasions. It’s the perfect starting layer for your favorite winter accessories, like a black leather shoulder bag, leopard flats, and a classic trench coat.

For a French twist, add a silk neck scarf, like this one from Banana Republic. If there’s one thing we saw in French street style looks, scarves are a great way to add your individual taste to an outfit!

Free Resource: Looking for more pieces that you would find in a French Wardrobe? MCO has a free French Wardrobe Shopping List that you can find here.

12. Scalloped Effect Dress

classy winter dresses outfits

dress | earrings | heels

This scalloped-effect dress is the perfect amount of shine to brighten up your winter look. It features a slightly-dropped waist, with a midi skirt. The classic silhouette would be a great choice to attend a wedding, or maybe a theater show.

Keep things simple by styling this outfit with kitten heels and emerald stud earrings, which will add the perfect pop of color to the look.

13. Draped Navy Dress

classy winter dresses outfits

dress | white pumps | square gold earrings

Navy blue is another stunning shade to include in your classy winter dresses outfits. The draping on this dress is not only a flattering style but also a look old-world style glamour that will elevate your look.

This long-sleeve dress will never go out of fashion and is the perfect piece to pull out for all of your cold-weather special occasions. Whether you’re headed to a nice restaurant for date night or a winter wedding, this is an easy dress to accessorize for many different types of venues.

Complete the look with a timeless white pump, and rectangular gold earrings that offer a structured contrast to the organic draping of the dress.

14. Elegant Strapless Dress

classy winter dresses outfits

strapless dress | floral choker necklace | slingback heels | feather bag

This daring take on the little black dress is the perfect way to make a statement with your outfit, even during the colder months. The longer length of the skirt on this dress helps to balance out the strapless top, and the classic silhouette makes this a timeless piece for your classy winter dresses outfits.

Because this is a simpler style of dress, add flair to it with your accessories by having fun with a floral choker necklace and a feathered bag. I love this bag because it’s just as much of a statement as a unique clutch, but offers more practicality in that it is easier to access what’s inside, and can hold more than a small, hard clutch might. Slingback heels complete the look.

15. Silver Maxi Dress

classy winter dresses outfits

dress | heels | hoop earrings

Shine in silver with this maxi dress. The metallic threads of this dress will have you feeling your sparkly dress, even if the weather outside is dull and dreary. The long sleeves are perfect for cold weather, while the silver color elevates the ribbed texture.

Add a pop of color to the fun look with these green heels. These are the perfect shoes if you’re not ready to let go of the bow trend (I know I’m not) and would also make for a great shoe come Christmas next year. Simple silver hoops finish out the style.

16. One-Shoulder Mini Dress

classy winter dresses outfits

one-shoulder cape dress | bangle | earrings | ankle boots

For occasions where a mini dress might be an appropriate choice, this is an elegant style. If you’re torn between a strapless piece and long sleeves, this is the perfect dress for you! The draping on this dress is an elegant touch, and the long sleeve is the perfect way to add a bit more coverage to the mini skirt style.

If you’d like to take a slightly more casual approach to this look, cream ankle boots, a mixed metal bracelet, and chunky gold hoops are the perfect accessories.

Classic Winter Weather Looks

Don’t get stuck in a winter wardrobe rut this year! Don’t be afraid to break out your fun, sparkly best – even though the holidays are behind us. And if you’re looking to add something fun to your collection this year, hopefully, one of the pieces above caught your eye. Whatever the occasion, don’t be afraid to shine this winter and have fun getting dressed in your best winter dresses that will be sure to turn heads.

Looking for more elevated, classic looks for winter? Up Next: 10 Old Money Outfits That Exude Class.


Hi, I'm Cassie! My husband and I have a full house with three furbabies, and when I'm not spending time with them, I'm loving all things fashion, travel, and romanticizing life's little moments. I'm also a self-described book nerd, and am always on the hunt for my newest read.