What to wear in the Winter - Outfit Ideas for when you are in a rut.

Home » What to wear in the Winter – Outfit Ideas for when you are in a rut.

It’s not easy to get dressed when it’s cold outside. I just moved to Chicago from Venezuela, so I can really say I have no idea what to wear in the Winter time. I don’t know how to look like myself and feel cute. It’s hard and way too cold to even bother sometimes, but today I’m making an extra effort and I’m putting together some outfits to hopefully inspire you to create a few Winter outfits of your own. I hope you like these outfit ideas for when you are in a rut.

When I moved to Chicago in May last year, everyone told me to watch out for the winter. I have to admit I was really scared. I mean I was actually cold in May when it was 60 degrees and I could not process how girls were wearing shorts and dresses while all I wanted was to wear a coat LOL. No matter how many warnings I received, deep down (very deep down) I was very excited for the wintertime. Being from an all-year warm South American country, I’ve never had the chance to experience cold weather and snow for more than a couple of weeks, so yes, I’m doing my best to soak it all in right now. It’s hard sometimes, I’m doing my best to stay positive, but overall I do like to live in a city with four seasons. I have been enjoying the snow every time I have the chance. It’s great to feel like a kid every once in a while.

What to wear in the Winter (and still look cute)

Disclaimer: These outfits might not be the warmest, especially because I don’t like to wear boots all the time, so just bear with me. If you have better shoes than I do and it’s an absolute necessity for you to have your feet warm, then try recreating the look but wear warm boots instead.

Look 1 – A classic neutral look

This outfit was definitely inspired by snow. I love neutrals, and I think they go perfect with winter. Sometimes is nice to give that black coat you wear everyday a little break. Initially my outfit was supposed to be with white pants but I’m still carrying some holiday weight lol so I had to go with grey pants that fit. I’m happy with the results. This is one of my favorite looks. You know why? Because it’s timeless! You can wear it every single year and never feel like it’s outdated.

Neutral winter outfit. Easy classic look for Winter

I must admit that the heels were only for the photo-shoot. Afterwards I wore a grey pair of suede boots (that you’ll get to see a lot in future posts) and took a nice long walk around Lincoln Park.

Links: Heels – Pants – Sweater – Coat – Scarf

Look 2 – An easy go-to outfit

I’m pretty basic with my clothes. I have tons of neutrals that I like to combine with different accessories, but since I decided to start a fashion blog, I’m trying to be more creative, not that much with colors but with textures and prints. Of course, always maintaining my unique style. I’m always ME no matter what. For this look, I combined military green, with a beige and gold sweater, ripped boyfriend jeans and my absolute favorite shoes right now.

This outfit works good for me because if I’m going out I’ll just add heels or booties and change my makeup. But the main reason this outfit is so perfect is because I’m comfortable with it and I feel beautiful because of that. You can always add a coat over it if it’s too cold, but the jacket I’m wearing is pretty warm. Perfect for a Winter day in the 40’s.

What to wear in the Winter - Easy go to winter outfit wearing all kinds of neutrals and jeans — What to wear in the Winter

Links: Shoes – Boyfriend jeans – Sweater – Jacket – Sunglasses

Look 3 – Winter look with an LBD and a jacket/coat

I created this look with a little black dress, tights, flats and a a jacket (that also looks like a coat? not sure what it is LOL) that I think is super chic. I got dressed really fast because I didn’t have much time but I thought that this basic street style was worth sharing. I’m wearing a long sleeve black sweater under the dress (Even though you can’t see it), an LBD from Loft that I love and I wore a lot during the winter and since it’s a short sleeve dress I can wear it all year round without the sweater. I love versatile clothes that you can wear any time just by changing the accessories. You will definitely see more of this black little number in future posts.

A classic winter look wearing all black and a classic cape — What to wear in the Winter

Links: Similar shoes – Warm tights – LBD – Similar Jacket – Necklace – Sunglasses

Look 4: Layering a trench coat

There comes a time during Winter where you are just over Winter coats! OVER THEM! That’s when your Spring Trench comes in handy. Have you done this? You just have to add a couple extra underneath. That’s why I recommend sizing up when shopping for a trench coat. I layered a chambray shirt and a sweater over a dress and of course, added tights too.

Layering some of my favorite pieces to create a classic winter look — how to dress in Winter

Links: Booties – Warm tights – Sweater Dress – Chambray Shirt – Sweater – Bag – Sunnies – Headband

Look 5: Skirts and Tights for the win

If you’ve been following along for a while perhaps you’ve noticed my love (or obsession) for skirts and tights this winter. Even though I do love this combo for various reasons (not having to shave being one of them!), I must confess that I’ve been dressing like this all the time because none of my pants fit! There you have it, that’s the truth LOL. I try not to buy bigger clothes and force myself to eat healthy and workout whenever things get out of control, which is what I’m doing right now, but in the meantime, this is how I dress.

What to wear in the Winter - skirts and tights for the win! — What to wear in the Winter

Links: Similar Booties – Winter Tights – Skirt – Jacket – Scarf – Sunnies – Bag

Look 6: Neutrals with a pop of color

Hope you like this outfit. I simply chose to combine black with any color (burgundy this time) and adding a cute black and white coat with a pop of color (the scarf). This pink scarf reminded me that spring is coming soon and I’m beyond excited for what next season will bring.

What to wear in the Winter when you don't know what to wear. Black and white with a pop of color — What to wear in the Winter

Links: Booties – Winter Tights – Similar Coat – Scarf – Sunnies

Make sure to check out these other posts too! There are over 200 Winter looks for you to recreate with things you already have in your closet.

How to Style a Long Cardigan – 7 Winter looks

Here you have a couple of videos I shared on my YouTube channel. Please have mercy because these videos are old and not super high quality, but I hope you still find them useful. The goal is just to give you ideas to style things you already have in your closet and get creative.

5 Classic Coats You Will Need Every Winter: