Hello there! It is officially cold here in DC, which is exciting when it comes to getting dressed because there are so many different outfits you can wear this time of the year, including a cute dress. Cold weather doesn’t have to stop you from wearing a dress! It might seem tricky to stay warm while feeling stylish in a dress during the winter, but I hope this post will help you feel your best even on the coldest days of the season.
I use affiliate links throughout this blog post, which means I might make a commission if you use my link and then make a purchase. This commission comes at no cost to you.
I was pregnant in this photo, but it remains one of my favorite ways to style a dress in the colder months. This is a simple shirt dress that I wore with knee high boots and a warm blazer. You can find my exact boots in black here, but they aren’t available in brown anymore!
A Few Tips On How To Wear Dresses In Winter
Winter outfits don’t have to make you feel frumpy! There are plenty of days where I embrace feeling frumpy, but if you’re putting on a dress this winter, I hope it makes you feel put together! There are lots of ways to stay warm while wearing a dress, too – from fleece lined tights to wearing a thin long sleeve top under a dress to knee high boots.
How To Style A Blazer Dress For Winter
A blazer dress is a great dress to have in your closet for after work hours. The cut of a blazer dress is inherently chic, so it’s nearly impossible to feel frumpy in a blazer dress. And, if you do, you might just need a different size. Anyway, you can wear a blazer dress to different holiday parties or gatherings throughout the winter, whether you’re going to a dinner with your friends to celebrate or you’re going to a work party. It’s super easy to style for any of these occasions by changing your shoes from boots to ballet flats or heels. I recommend wearing tights no matter what shoes you’re wearing. You can also layer a blazer dress with a thin turtleneck sweater for added warmth (or ultra professionalism).
How To Style A Slip Dress For Winter
You might think slip dresses are best as summer dresses, but they’re really easy to layer with a sweater for a warm and chic winter look. This is actually one of my favorite ways to wear a slip dress. You can wear an oversized sweater, a regular fit sweater, or a cropped sweater – it just depends on your personal preference. You can also add a belt too! I typically wear knee high or over the knee boots with this type of outfit.
How To Style A Shirt Dress For Winter
If you’re heading into the office all winter, a shirt dress is a good option for your work outfit rotation. They look really nice with knee high or over the knee boots. The most important thing about wearing a dress in the winter with boots is to make sure your boots are tall enough to meet, or preferably, go above your dress hemline so there isn’t a space between your dress and shoes. This way, you’ll stay warm!
How To Style A Sweater Dress For Winter
Sweater dresses are pretty easy to style since they’re made for the cold weather! They’ll go with just about any pair of shoes, whether you want to wear boots with a high heel or comfortable sneakers. You can wear these dresses loose for ultra comfort or you can wear them with a belt for a more polished look.
Simple Slip Dress With A Sweater And Boots
Here are a few outfits you can easily recreate! This first look is super simple. I wore this black slip dress with an oversized sweater, belt, and over the knee boots to meet friends at a holiday-themed bar. You could also wear this with a more cropped sweater or a super oversized sweater. If you want to dress this up, go for boots with a heel. Use code YOUROCK for 20 percent off my exact boots. They also come in other colors, and they’re waterproof!
Slip Dress With A Velvet Blazer
I also love to dress up a black slip dress with a blazer, and this black velvet blazer is absolutely perfect for the winter! I love how it has welt pockets, so it won’t widen you at the hips, and the buttons are gorgeous. Sezane never misses a beat when it comes to perfecting details.
Same Color Sweater Dress And Boots
There’s nothing easier to wear and better looking than a monochrome outfit if you ask me! I love how leather boots look against a sweater dress in the winter – they help elevate an otherwise simple dress, and both pieces stand out because they’re different textures. The first dress I linked is by the same brand and the most similar to the one I’m wearing. I wore this outfit for family photos in London. You can easily create this look with any sweater dress and boots you already own. While my dress came with a tie in the same fabric, a leather belt will also look nice with a sweater dress – just make sure it works with your boots.
Shirt Dress With Boots And A Cashmere Wrap For Work
If you like to be able to wear your work wardrobe on the weekends or your weekend outfits to work, this striped shirt dress is a great option! I styled it here for a work day with knee high boots to keep warm, and the heel is low enough that you can easily move around. I own this exact cashmere wrap in two colors, and I wear it all winter. It feels just like a cozy sweater, but it’s way more versatile. You can wear it with this dress as a scarf during your commute and around your shoulders at your office. These sunglasses are so fun! Click here to see them on me. I absolutely love Cuyana after recently visiting their Boston store, so I included this bag because they make really great work bags!
If you’re looking for other work outfit ideas this winter, check out my post on putting together a business casual capsule wardrobe.
Cashmere Sweater Dress
I’ve been eyeing this cashmere sweater dress since I saw it in store this fall. It’s just gorgeous, and it is so soft. I love this for a weekend, holiday party, family party, or a weeknight, but I probably wouldn’t wear it to work. This color is the perfect chameleon – you can wear it with black, brown, navy, burgundy, or even dark green shoes. You can really wear it with anything!
Denim Shirt Dress
My denim shirt dress is the perfect denim dress. It’s soft, the perfect length, and it has a forgiving waist. I knew I would get a lot of use out of it this fall, but I also love how it looks with knee high boots or over the knee boots for winter. This pair of dark green suede boots would be so fun with this dress. Anyway, this dress is perfect for work or a date night. You can also wear this with tights! My dress was gifted without any obligation to share – I just really love it. Use my code NATALIEM20 for 20 percent off!
Holiday Party Dress With Silver Accessories
This dress is perfect for New Year’s Eve inside. How fun is the shimmer detail on this fabric? I love how it looks without a belt, but you can definitely wear it with a fun silver belt or black belt too.
Maxi Sweater Dress With Boots And A Belt
A maxi sweater dress is easy to style for cold months. You can wear it with matching boots and a belt, and be out the door in 10 minutes! This type of outfit is perfect for the weekend, a dinner out, and it’s kid friendly. I was newly postpartum here, so it works for new moms too. I love the look of this gray maxi cardigan dress – it would be a great option if you’re pregnant too.
You. might’ve noticed by now that I’m only styling these looks with taller boots. If you’re wearing any type of dress this winter, I recommend avoiding ankle boots for the most part – they tend to shorten you with a dress and they aren’t as warm as other boot options!
Tweed Blazer Dress With Knee High Boots And Turtleneck
I was recently gifted this tweed blazer dress, and it’s really perfect for any holiday parties you might go to. Use my code NATALIEM20 for 20% off. This dress is appropriate for a work party but you can also make it a little more fun for a get together with friends or a date! Anyway, for work, I would wear it with this tissue turtleneck underneath, black tights, and black boots. Size up in the turtleneck! On sizing for the dress, I’m a size 28 waist and I’m wearing a medium.
From midi dresses to a shirt dress, there are so many ways you can stay warm in these dresses. Did you find any helpful tips or outfit ideas for wearing dresses in the winter? Let me know what you think!
