Stunningly chic Winter dresses from casual to cocktail
Winter dresses don’t have to mean just sweater dresses, although I’m a huge fan of them too. The styles on here are the most versatile dresses to add to your winter wardrobe to be able to dress up or down for the office or after work parties. Whether your styles modest, classic or fashion forward. For Winter dress trends 2023 think leather, hot pink and red, maxi dresses, corsets and subtle bow details. The Valentino dress below is perfection for this. Keep reading for the best chic casual, formal and classy winter dresses to wear during the colder months. Here’s lots of winter outfit ideas that nail all of the winter fashion trends to wear during the coldest months of the year and how to style them for extra warmth.
This post contains affiliate links.
Shop the winter dress edit
From designer to luxe for less, everyday outfits to formal Winter dresses, these are the most stunning styles around this winter season.
- Alice & Olivia black and white Tuxedo dress for an elegant and chic style.
- Alice & Olivia zip front pink tweed dress makes a simple tweed dress look more modern.
- ANKVAS neoprene mini dress is the most stunning structured teal bodice dress.
- You can never go wrong with a classic LBD black and gold button mini dress.
- Balmain glittery monogrammed mini dress might be a little glam for the day but I say during the festive season bring it on!
- Balmain jacquard knit mini dress is a total knock out but don’t expect to blend in in this designer Winter dress. This is made to be a stand out.
- For a look that says straight off the runway, Valentino‘s bright orange long sleeve dress with feather cuffs is fun, stylish and perfect for all of your holiday events. If you don’t normally wear a ton of color in the Winter, change things up with this outfit.
- Assignment black and white long sleeve houndstooth mini dress is easy to dress up or down for work or cocktails. The best part about this classy winter dress is that it also comes with the belt which is detachable so you can wear it with your other winter dresses too.
9. This long sleeve pink satin dress is another mini dress that works for the day or night.
10. I started this as more of an everyday winter dress edit but got distracted by pretty things like this black leather strapless dress for under $100. It’s one of those sexy dresses you could down play for work with a white shirt underneath or a blazer, tights and boots. Then add a red lip and get rid of everything but the dress for the night.
11. Comfy casual at its best. Brand du jour Skims long sleeve soft lounge dress is the casual winter dress that keeps selling out. It comes in lots of different colors and sleeve lengths.
12. Black blazer dresses are a classic option for Winter dresses and especially the office. Express has some really good sales on right now and this dress is in it for just over $100.
13. This off the shoulder denim maxi dress works for all seasons with some clever layering and the length is right on trend. When you think denim you think casual Winter dresses but this is a style that can easily be dressed up or down.
14. This formal winter dress is such a classic ivory midi that would work for pretty much every season. It’s cut for a flatteringly slim fit and such an ultra chic look.
15. If you’re bored of neutral colors, Valentino crepe neck dress comes in the hottest color of the year, fuchsia. Which works for pretty much every occasion and makes for a super cute and stylish winter outfit. The long sleeves also give a little more coverage and warmth for Winter.
16. Reformation‘s relaxed high neck, long sleeve mini dress is perfect for the holiday season and layering with tights and boots.
17. Classic style Valentino, this cute winter little black dress has an elegant and on trend bow detail. Layer with tights and knee boots on colder days.
18. The ALLTAA illusion midi dress is probably the most interesting winter dress on here. This black winter outfit looks like a ribbed knit turtleneck sweater and faux leather skirt but is actually a dress. It’s probably the most perfect winter outfit for the office on here.
19. Dior black and white houndstooth sleeveless dress is a classic but statement dress you can wear year after year. If you’re worried about being cold, you can always layer a blazer or oversized sweater over the top and add tights and knee-high or thigh-high boots.
20. Black sleeveless blazer dresses are ideal for layering over shirts or wearing on its own if you run hot. It’s a style you can wear year after year without worrying about it being out of style.
21. For an on trend formal winter dress, this partly sheer, cut out black midi dress is one of the best winter dresses for being fashion forward and sexy while staying chic. It’s also under $150 and comes in navy, black, burgundy or brown.
22. If you’re looking for navy blue to make a change from black, this long sleeve bodycon dress would work for winter weddings, the office, date night and pretty much everything in-between. It’s a super versatile, classy style that’s under $100.
How to style winter dresses for extra warmth
If you’re worried about staying warm in any of these cold weather dresses, you can easily layer a puffer coat, wool long coat, long cardigan, faux fur jacket, chunky sweaters or soft knits over most of them for extra warmth.
I know it’s not sexy but a thermal bodysuit and even thermal tights or leggings also work wonders! I’m all about layering rather than one thick layer in the cold winter months as otherwise I tend to overheat inside.
For more daily style tips and sale alerts.
More Winter fashion
The winter dresses and winter trends to update your wardrobe this season.