How to Dress Up in the Winter: Outfit Ideas & Fashion Tips to Try

For years, after having traveled full-time and worked online, I got pretty lazy with my wardrobe.

It was so easy to just want to pack up as little as possible because when you move almost every month, it gets a bit tedious.

But finally, I had enough and decided to start planning out my wardrobe. Something that could work for travel and keep me fashionable. And now, I want to help you if you’re also struggling to build out your own wardrobe that makes you feel confident.

Now one of my favorite times of the year to dress up is the wintertime. As the temperatures drop, I love the textures, layering ideas, and creating elegant winter outfits for the season.

And if you’re looking for some good tips on winter styling, then here are some ideas on how to dress up in the winter, look chic, and still stay warm.

1. Understanding the Basics for Winter Outfits

I feel like it’s important to start off with the basics for winter fashion before giving outfit ideas. So here are some quick tips for some items you might want in your closet and staying stylishly warm.

• Accessories that keep you warm: This one is simple but so important if you’re trying to learn how to dress warm and stylish in the winter season. Thermal or wool tights are great if you want to wear skirts or shorts or dresses, but they’re also great for wearing under a cute pair of pants so you’re not freezing! Also, socks, scarves, beanies, boots, and gloves are great options for looking fashionable and staying warm. Also, if done right, they can make a really good fashion statement.
• Water repellent: Plain and simple, make sure to use water repellent to keep your shoes nice and your feet dry and warm.
• 3 fashionable coats to look out for: If you want to stay fashionable and warm, then here are 3 coat ideas you should look for. Waist-defined, belted, and peacoats. These three will help you look amazingly fashionable and effortlessly put together. Especially peacoats! Get it in a neutral and it dresses up almost any outfit. It’s such an easy way to level up your winter style.
• Choose the right colors for your winter wardrobe: Ok, now obviously you can wear whatever color you want, but here’s my opinion. If you have a lot more neutrals than one-off vibrant colors, they can give you a lot more clothing combinations and outfits. I’ll go into that more down below when I talk about winter wear!

2. What to Have in Your Winter Wardrobe

Ok, first off, these are all just ideas, not mandatory! But these can make for a lot of great outfit combinations for your winter wardrobe.

So here are some ideas on how to look stylish in the winter and dress well:

Camel Coat: It’s a great neutral that works with so many outfits and makes you pop in the dark grey weather. Also, you kind of just look like a model. 🤷‍♀️

These look great with black pants and a black sweater, but obviously, you can wear it with other pieces. So for instance, I wore mine, down below, with dark blue jeans, a black sweater, and a black belt and flats. 

Black Peacoat: Don’t ask me why I decided to do almost the exact same pose, I don’t know, I guess I just liked it!

But yes, peacoats can help to create elegant classy winter outfits and make you look really put together. I was headed to another state to see some family and this was a comfortable and easy outfit for the day.

Black, light blue, and dark blue jeans: As you can see above, the different jean colors are a great way to make an outfit pop and look casual but fashionable.

A thin tan and/or black belt: When I was younger, I always felt like belts were kind of lame. I don’t know why! Maybe it was becuase growing up, I saw adults wearing them and it just didn’t look cool. But then something shifted around the age of 25 and suddenly I thought tucking in tops and wearing belts was awesome. And honestly, belts really are a great way to dress up an outfit!

Black, grey, and white sweaters: They’re warm but also so so simple and take a second to put on. And as a plus, they’re cozy and make you look super cute. Tucked in or not, they’re a great essential to have!

Black, grey, and white turtlenecks: I think turtlenecks are such a easy way to dress up an outift. And whether it’s form fitting or loose, they look great tucked into some cute pants. Also, they’re such a nice way to stay warm when the temperature dips.

Henleys: I love Henleys, they look a bit laid back but also super cute and fashionable when they’re form fitting. I personally have a dark red and grey one, but there are plenty of other colors you can get if you want your outfit to pop more!

Thick black tights: These honestly go with so many different cute outfits. You could pair them with shorts, skirts, and dresses. It’s an easy way to make clothing pieces that shouldn’t work in the winter, just work.

Black and tan flats: Ok, so this one might be a bit more for fall, but if you’re not so cautious (like me), and are fine with wearing flats in the winter, they’re a great way to look fememnine and put together.

Winter boots and tennis shoes: I know it’s weird, but I don’t own boots at the moment. Hower, I have in the past and they do come in handy when it’s cold. Which is obviously a given. So I don’t think anyone’s arguing over the neccessity of them. But for cute tennis shoes, I own some dark grey and black addidas and light grey shoes which can make the outfit look casual but smart.

Scarves: An obvious yes and a simple way to make your outfit look great, and keep you warm.

3. Brighter Colors for Your Winter Wardrobe

I know that I told you to mainly get neutrals for your winter wardrobe since that would make sure you have a lot more clothing combinations. But here’s where I tend to stray from that rule. 

Picking one color that pops for your winter wardrobe is honestly a great way to look fashionable.

Here’s what I mean: You have a lot of cute neutrals right? But one of your favorite colors is pink and you’d like to still work it into your winter outfits. So here’s what you can do. Buy a dress in a shade of pink you like (and/or a skirt). Get a top or another garment that has a simple but cute pattern with some pink in it. Or a pink blouse is always a great idea! 

So basically you want to keep things a bit minimal when it comes to having bright colors in your winter wardrobe. You can still pop when you want too, but it’s not overwhelming and there aren’t pieces that don’t go with each other.

I hope this makes sense! ♥️ 

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Now of course, this is all subjective and you can pick and choose what tips you want to try, but I hoped this helped make things simpler on you! It’s not always easy when you’re trying to elevate your winter style, but with just a few ideas, it can definitely take away some stress and give you an amazing winter ensemble.

PS – What are your favorite winter pieces?