Inside: Trendy and classy winter outfits for the cold weather lovers and haters alike. Be cute while braving the weather.

Winter is easily the hardest season to dress for.

At least for me, down here in Texas.

It’s especially hard for me when I have to try to dress up and dress nicely in the cold months, because I don’t gravitate towards winter fashion. Sure, I can throw on a nice coat over a summer dress and call it winter, but sometimes that just won’t do.

That being said, I do absolutely love winter coats and shoes– with the exception of all the combat boot trends, they tend to be a little dressier, a little nicer, and a little more elevated. Summer we’re all just trying to beat the heat.

As holiday parties roll around and you’re getting flashy and bold while hiding from the cold, you’re going to love some of these classy winter outfits for this season.

Need some tips? Inspo pics? I’ve got it all for you in this post.

Three classy winter outfits

How To Dress Elegantly In Winter

Dressing elegantly in the winter time can be effortless if you know how to play the cards right. The coats and the holiday party outfits are all so classy and timeless, that if you invest in a lot of the right staples, they’ll lend to an overall elegant and classy winter wardrobe.

And they’ll last for the next few seasons, throughout many shifts in trends.

Some timeless winter pieces that can create an elegant look are:
Pea coats
Trench coats
Black pumps
Plaid pumps
Plaid dresses
Black slip dress (midi length)
Velvet anything

These are just a few that I always try to keep in my closet for a quick and simple elegant winter look. There are so many different items you can use to keep a classy wardrobe for the winter, and it all depends on how you utilize and wear each piece.

Elegant and classy aren’t narrowed down into a few pieces, but in how you style and wear everything you own. We’ll get into some examples soon, but just know that using a few different elegant and classy pieces will make your winter outfits pop.

Even a classic pump with a pair of jeans and a trench coat will do the trick– it might be a little chilly on the top of your feet, but it’s the price we pay for elegance in the winter.

2023 Winter Trends

Every season we’re seeing huge shifts in trends from the same season the previous year. The trend cycles move so fast, it’s hard to keep up. And don’t feel like you have to! It isn’t sustainable for anyone to keep up and stay on trend all year every year, so let’s just chat about the ones that are going to help you elevate and make your closet a little more elegant when it comes to the winter time.

Maxi skirts are huge this year. A very summery look but can be made to look like a winter fit for sure. It’s a little bit more elegant in the ethereal sense, not as much the preppy and classy, but elegant nonetheless.

Faux fur is all the rage! Some say that it’s specifically attention-grabbing fur is the move, but anything that adds a little flare and something a little wild and extra to your outfit with faux fur is a huge win.

High boots are back! They’ve never left, they simply became a staple. But a new edgy silhouette or shape of the boot will refresh your over the knee boot looks. Wear with a blazer dress, a mini dress (since your legs will be covered, obviously), or overlapped with a midi, and you’re golden.

High fashion trends like to be a little reminiscent while looking forward at the same time. If you have the vision to, see how you can work some of these very 2000’s styles into your winter wardrobe for a very chic and elegant look while staying on trend with this very grunge season.

Little Tips For Staying Warm

I’m not quiet about it, but I’m from Texas but I do spend a lot of time in New York City.

That being said, I needed to be pretty prepared for the weather change when I first made the trip up to the Big Apple, I had to find all the tips and tricks to dressing cute but staying warm in actual cold weather. It can get cold in Texas for sure, but we make a run for it to the car and warm it up, we don’t walk around town in it here like New Yorkers do.

So what do I do?

I couldn’t travel New York in the winter without these few items: fleece lined tights, ear muffs, and a face mask.
Covid obviously changed the way people even walk in the streets in some major cities, and I realized while visiting New York for an internship in February that it actually was majorly helpful when keeping the bitter wind out of my face. While you may not be wandering around somewhere that you want to wear a mask, it was a major game changer for me!

Utilizing the fleece lined tights and the cute ear muffs that you can find just about anywhere these days will save you. Whether you’re heading to an outdoor event or you need to wander around the shopping center and still look put together, these pieces will help you achieve the goal of warmth for any occasion.

Four chic outfits with coats and sweaters


Aiming to dress chic for any occasion will be a huge win. Chic is never out of style, and is always achievable in winter.

1. Tan And Black
2. Trousers
3. Oversized Scarves
4. Beret
5. Cool Blazers
6. Long Gray Coat
7. All Black
8. Pink Sweater
9. Cool Jeans
10. Brown Blazer

French girl inspired outfits

French Girl Inspired

The French girls do winter style the best. Let’s take some inspiration from them, shall we?

11. Navy Trim
12. Striped Sweater
13. Plaid Blazer
14. Gold Buttons
15. Puff Sleeve Sweater
16. Tan Trench
17. Slouchy And Loafers
18. Layered Florals
19. Red Pop
20. Flare Jeans

Night time outfits for cold weather

Night Time

Night time outfits are always the classiest, and the coldest! Check out these classy winter outfits for the night time events and happenings.

21. All Black
22. One Shoulder
23. Black Sweater Dress
24. Suit Pieces
25. Tights And Pumps
26. Leather Pants And Pumps
27. Silk And Leather
28. V Neck Dress
29. Red Faux Fur
30. All Red

Four women in nice winter outfits

2023 Classy Winter Outfits

31. Collared Layers
32. Rust Sweater Dress
33. Brown Dress
34. Teddy
35. Long Herringbone Coat
36. Big Blazer
37. Suede Coat
38. Button Down Dress
39. Split Skirt
40. Drop Shoulder
41. Layered Mesh

I’ve said it before and I will say it again. Winter is the hardest season to dress for, hands down.

While all of the pieces are pretty and ideally they create this beautiful winter aesthetic, it’s simply just hard to execute it in the way that it actually looks the way you want it to in your head. Whether that’s due to frumpy coats or too many layers to feel cute in, there’s always something.

But hopefully these tips are helping you to eliminate these factors from some not-so-cute winter outfits so that you can create the stunning classy winter outfits of your dreams. All it takes is some minor adjusting and a little tweaking to pieces you already have and some that you have your eye on and it will amaze you what you can do with your style.

Heading to a winter wonderland?

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