How to Dress Comfy This Winter + 4 Outfit Ideas!

Hi, lovelies! 💛 I hope you’re having a great week! Wow… it’s COLD in Chicago at the moment (27 °F as I’m writing this to be exact). I’ve lived in the windy city since I was 5 and somehow the frigid temps seem to surprise me every year. Picking out that photo-worthy outfit you won’t freeze in is a challenge sometimes. However, you can totally dress comfy this winter!

Personally, I’ve been loving quite a few awesomely comfortable trends this season. Can we talk about those statement fuzzy jackets.…they’re so cute! I also can’t forget about colorblock clothes, oversized sweaters, boots, and so much more!

How to Dress Comfy This Winter

For this post, I include tips that will hopefully make shopping a little easier when it’s this cold outside. Some of the pieces are linked, and I tried to find comparable pieces if mine aren’t still available online. 😊

With that being said, here is my “how to dress comfy for winter” tutorial!

I’ve compiled a list of winter outfits that are both stylish and comfortable! ☃️

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The “Business Casual” Outfit

When it comes to work, building up your wardrobe can be an overwhelming process. I remember feeling really stressed about finding work clothes for my first job after college. I had no idea what “business casual” even meant. On top of that, I wanted to find items that I’d be able to wear outside of work.

Eventually, it got so much easier! If you’re starting your first job, make sure to take deep breaths throughout the shopping process. You’ll build up that collection as time goes on and find your go-to pieces! These are just a few tips that’ll hopefully help along the way!

1. Try a knit pullover sweater

In the wintertime, it’s great to stack up on a few sweaters for the workweek. They’re easy to style, chic, cozy, and warm –- perfect for an office environment.

I recently bought this cable knit pullover sweater from Charlotte Russe, and it’s so comfy! The sweater’s material is thick and super soft. It also keeps me warm (but not overheated) during the workday! Side note, why are offices always so cold?

2. Layer with scarves

It’s hard to concentrate on your tasks if you’re freezing or uncomfortable, so make sure to layer! A cute scarf adds such an elegant touch! Lauren Conrad has a beautiful selection of scarves at Kohl’s for only $16!

3. Stretchy dress pants—A MUST!

For pants, try to look for anything stretchy and easy to move in. Express’ Barely Boot Columnist pants have awesome reviews. If your job is a little more relaxed with the dress code, I recommend black dressy jeans. Charlotte Russe has high waisted black jeans that easily pass as dress pants.

4. Go for low or no-heel shoes

Finally, shoes! Gosh, I love shoes lol! Maybe you’re walking or standing up a lot throughout your shift. It’s best to search for shoes with little to no heels. If you want to dress comfy, ankle booties are such a stylish choice. Forever 21 has some gorgeous options on their website!

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The “Night Out” Outfit

Maybe you’re going out for drinks with pals, enjoying a romantic date night with bae, or dancing the night away! No matter what the scenario may be, your comfort is super important!

I’ve always struggled the most with finding that perfectly cute but cozy “night out” outfit. Evening attire sometimes comes with pretty itchy fabric and uncomfortable styles. (I’m looking at you, bodycon dress and stilettos!) There are definitely comfier alternatives, though!

1. Stay warm with a chic turtleneck sweater

Since January can get quite cold, make sure to bundle up. A turtleneck is a definite winter closet essential. You’ll look effortlessly chic, and this winter staple will keep you warm throughout the entire night! Turtlenecks came back in style in 2018, although they’ve always been pretty timeless!

2. Add a faux leather jacket

If you live in a place with milder temps like Cali or Oregon, you probably won’t need a puffer jacket and gloves. Opt for an adorable faux leather jacket instead! You can pair the jacket with just about anything, and almost immediately feel more dressed up.

3. All about trendy skirts!

Instead of an evening dress, consider changing things up with a trendy skirt! There are so many styles to chose from…pencil, mini, pleated, midi, the list goes on. Mix and match a fun printed skirt with a more formal sweater. Throw on some cute shoes or boots, and you’ll be good to go!

Some CUTE skirt ideas for your night-out look–

• This adorable sequin pencil skirt from Francesca’s.
• A polka dot mini wrap skirt from ASOS.
• The loveliest corduroy button front skirt from Francesca’s

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The “Everyday Wear” Look

On the weekends especially, often times we’re running errands or trying to get things done around the house. Many people also work from home during the weekdays, bloggers included! In this case, it’s essential to find fashion staples that make you feel like you’re ready to take on the busy day!

1. Bring out the oversized flannel

An oversized flannel is such a classic wardrobe must-have when it comes to comfort. Flannels never seem to go out style, either! I tend to steal Alejandro’s or shop in the men’s section for my flannels. In these pics, I’m wearing a forest green Croft & Barrow flannel. It’s SO comfy, I’d definitely recommend! ASOS also has a bunch of cute flannels on their site!

2. Leggings, leggings, leggings!

You can never have too many leggings in your closet! Stock up on leggings in various styles— everyday, activewear, cropped, etc. Target has great quality and affordable leggings, as does Aeropostale and Forever 21.

3. Style your daytime outfit with combat boots

If you want to dress comfy and add a touch of glam, try pairing your outfit with combat boots! In November, I bought my first pair of combat boots and fell in love hehe! They just look so effortlessly cool! Kohl’s has so many cute combat boots on their website, including these madden NYC Hazie Women’s Combat Boots!

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The “Coffee Date” Look

Afternoon coffee dates are already so comfy to begin with! I’m envisioning the aroma of fresh coffee brewing, the muffled sound of voices as strangers chitchat about their days, and that very first sip of a yummy hot caramel macchiato! The best! On that note, here are a couple of ah-mazingly cozy essentials for your next wintery coffee date!

1. Fuzzy cardigan + high waisted jeans + funky boots = LOVE!

Nothing says “comfy” quite like a fuzzy oversized cardigan! It’s also totally glam and brings a little bit of “extra-ness” to your outfit, which is just so much fun! I bought my fuzzy cardigan from Aeropostale back in November, but Fashion Nova has a comparable fuzzy sweater on their website! It’s also pink! You’ll definitely rock the look with a pair of high waisted jeans and some funky boots!

2. Accessorize with a funky bag!

For the last “coffee date” fashion staple, don’t forget your mini backpack! It’s the perfect accessory to store your laptop, notebook, and necessities! YAY functionality!

More adorable backpack options, because…accessories!

• CALPAK Kaya Backpack from Francesca’s
• T-Shirt & Jeans Two Tone Cat Mini Backpack from Kohl’s
• Mini Dual-Zip Backpack from Forever 21

I hope you enjoyed this post, lovelies! 💗 Have a wonderful rest of your weekend! x

What are some of your fave comfy winter fashion staples?

Grab an iced coffee & stay a while! 

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