How I Stay Warm in the Winter (While Trying to Look Cute)

Today I’m updating this post that I wrote a while ago but is still totally true today! Now that I’ve moved from Southern California back to my Northern Californian roots, these tips have been top of mind for me. So, I thought I’d re-share this post and update it a little with what I’ve been doing lately for how to stay warm in the winter—while trying to look put together!

When I originally wrote this post almost four years ago exactly (!!), I hesitated because I’m from California with mild winters, so obviously there’s a lot I still have to learn about cold-weather dressing. But the reason I wrote it was because I was on a lot of trips for work and traveling often to places that are much colder, like to Chicago, St. Louis, and Madison during the dead of winter (though, mostly Chicago—brrrr!) and I was figuring out what to wear. On my trips, I was with people from New York, Chicago, Michigan, Minnesota, and Washington DC—all with colder winters than where I came from—and they were always freezing while I wasn’t. I mean, I was cold sometimes, but others were FREEZING. (There were also people from Vancouver and Toronto, but they were totally fine! 😄) I started to wonder why I was faring better in the frigid Chicago temps and wind chill compared to 5 other people who lived in colder climates and were more used to the weather—especially because I’m definitely one of those people who runs cold and is NOT “warm blooded”!

So, in case it’s helpful for anyone, I though I’d share ways I like to layer up to stay warm (without feeling like a stuffed sausage 😆). Like I said, I’m from California with comparatively mild winters, so obviously I’m no expert. But I’m just sharing in case any of this helps you feel more comfortable as you navigate cold weather style. And since I’m sure there are even better ways to go about this, if you’ve got great tips to share, please do!  

For context, this is just for day-to-day stuff, like going to and from meetings and running errands during the winter, not actually playing in the snow or anything like that. We were walking around the city, using public transportation a lot, and spending time outdoors quite a bit though, and often temps were in single digits or low double digits plus wind chill.

BTW, I also updated the links and included some current pieces that you can shop in the widgets under each section. For SIZING info, I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.

Anyway, basically, I dressed in tons of layers while trying not to look like I was bulked up with layers. Below was my typical “formula.”

How to Stay Warm in the Winter and Still Look Cute

1.  Camisole – They’re usually thin and help keep my core warm. Don’t underestimate keeping your core warm! I just wear camis from Old Navy and have been for years. Find them HERE. Update: I usually don’t wear this layer while I’m in California anymore unless it’s really, really cold.

2.  UNIQLO HEATTECH – I’ve talked about these before, but I love these things. HEATTECH is a very thin layer that is soft, smooth, and stretchy, and never loses shape. They are formfitting without squeezing you (unless you get the wrong size), so that you can have an additional layer without bulk. The sleeves are intentionally a little short so that the layer stays hidden under your shirts or sweaters. I also get the scoop neckline to stay hidden under open neck tops. They come in several colors, but I just have nude and black. For sizing, I’m 6/8 or S/M and get these in M. Find them HERE.

They also have thicker ones, like the “Ultra Warm” HEATTECH which I also wear, depending on what I’m wearing on top. Sometimes the Ultra Warm is too thick to go under blouses, but they work well for thicker or looser tops. I also sometimes like those just as a layer on their own for sleeping or lounging. Otherwise, I stick to the thinner, standard HEATTECH.

I pretty much wear one of these every day under everything. I also make sure to tuck it into my pants to keep me better insulated. That also helps you do a front tuck with your “real” shirt that you’ll wear on top. 😊 Pic of the scoop neck HEATTECH tucked in below!

How to Dress Warmly in the Winter: heattech layer tucked into skinny jeans


3.  Long Sleeve Tee – Sometimes this would be a cotton long sleeve tee and sometimes it would be a long sleeve or 3/4 sleeve blouse. Back when I was traveling to Chicago often (falls and winters of 2009 and 2012) the only striped tee I owned was a yellow/grey thermal type one from Target, but it was pretty thin. If I were to do this formula today, I would wear a striped tee like THIS, a thicker thermal like THIS (you know I love this thing because of how well it drapes!), or a blouse, depending on what I needed to dress for. I wear the thicker thermal tee in size S.

This layer was important in case I peeled off layers once inside with blasting heaters, since I wouldn’t just wear the HEATTECH layer as my main shirt.

How to Dress Warmly in the Winter: cotton long sleeve + button up + long sleeve blouse
Shop Similar Pieces:

Below is me wearing a striped tee over the HEATTECH. It just looks like I’m wearing a striped tee, except I’m extra warm thanks to layers!

How to Dress Warmly in the Winter: black and white striped long sleeve top + heattech layer under + blue skinny jeans

4.  Cardigan, Sweater, or Fleece Zip Up – Back in 2009 and 2012, I usually wore a white fleece zip up instead of things like oversized cardigans. The one I had was from Gap (I still have it, haha!) but it was camouflaged under my white outerwear that you’ll see below. That helped the whole thing look streamline instead of mismatched or haphazardly thrown together. My fleece was very plain and more fitted than loose. If I did these layers with my style today, I could substitute a pullover sweater or one of my oversized cardigans for the fleece zip up. However, I still find fleece is much warmer than a cardigan!

Nowadays, if I’m not wearing a pullover sweater or a cardigan, I’ll wear a sherpa or fleece zip up type of thing instead of the zip up fleece. I usually wear the Fluffy Yarn Fleece from UNIQLO, which you can find in LOADS of colors HERE. It is VERY SOFT and WARM! LOOOOVEEEEE it! I wear size M, so I recommend sizing up. I also wear the Faux Shearling Zip Up Jacket from Z by Zella that I’ve shared several times on the blog. Find it in a few colors HERE. I wear that in size S.


How to Dress Warmly in the Winter: oversized cardigan or pullover sweater or fleece zip up

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How to Dress Warmly In the Winter: Grey Sweater + Heattech Layers + Blue Skinny Jeans
Comfy sweater on top of the other layers!

5.  Down or Wool Coat that Goes to Your Thighs or Knees – I WISH the particular coat I have was available today, but it was a random lucky find from Costco in late 2008. I bought it for a trip to Chicago, and it totally works for the occasion. It keeps me sooo warm, but it is SO thin. Much thinner than other down coats I’ve tried. I can roll it up and it only fills 1/4 of my carry on suitcase—it’s amazing! And, since there was no price tag and it was the last coat in the store, Costco sold it to me for $25. WHAT?! YES! #luckyday

Winter Coat White Puffer Coat + Scarf

It also almost goes down to my knees, which means that if I’m wearing riding boots to keep my legs warm, the down jacket keeps most of the rest of my body warm. That extra length is so important! Several of the other women I spent time in Chicago with only had pea coats or ski jackets that went to their hips, and they were so cold all the time.

6.  Scarf – A must! I’m infinitely warmer when I wear a scarf. The ones I had at the time weren’t even that thick. If I were to go to Chicago tomorrow, I’d bring a thicker scarf, like a knit scarf or a blanket scarf.

7.  Knee High Boots – Because these cover more of your leg, I find I’m so much warmer in them. None of the other women I was with in Chicago wore knee high boots. The one other woman who had a long down coat like mine was from New York, and she wore ankle-height shoes and was always really cold still. I think I was warmer than her because of the camisole and HEATTECH but also largely due to the taller boots.

How to Layer to Stay Warm in the Winter: jeans + knee high boots + scarf + long down or wool coat
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 jeans #1, jeans #2boots | scarf (in the color “Yellow”) | coat #1, coat #2, coat #3, wool coat


8. Gloves and Hats – And then, if and when I needed to, I added gloves and hats to stay even warmer.


With all of those layers, the trips to colder weather places were actually pretty bearable! I didn’t feel bulky or feel like a stuffed sausage 😂, rather I felt pretty stylish AND warm. One other thing to consider is clothing material, of course. Thicker tops and thicker sweaters will help you stay warmer than thinner tops, and certain materials are better for warmth than others. But, even without being super mindful of materials, layering like this is pretty effective. I liked that it allowed me to make some of the clothes that I wear in other seasons work in the winter, too. I also found layering in this way extremely helpful for managing the wide range of temps from super cold outdoors to really hot indoors due to the blasting heaters. When other people were wearing huge sweaters under their coats but didn’t have thinner shirts underneath the huge sweaters, they were often sweating once we got inside. In contrast, I could peel off layers, down to my long sleeve stripe tee or blouse, and be fairly comfortable indoors.

Now that I’ve moved from Southern California to Northern California, I need to dress warmer in the winter than I used to on a daily basis. However, it doesn’t compare to Chicago or other places 🥶, so I don’t need all of these layers. I usually skip the cami and only wear HEATTECH tops underneath everything. Those things are SUPER helpful! I also don’t often need tall boots, but I do opt for sneaker booties with faux fur lining which keep me cozy and still cover my ankles. I haven’t needed accessories like scarves, gloves, and hats yet, but I’ll definitely throw them on as needed.

Here’s a fun graphic putting together everything we talked about with my typical layers for California these days:

Layering Ideas to Stay Warm and Look Put Together

I think that’s all I’ve got for you! How do you typically dress to stay warm but look cute? Do you have an additional tip to share? Favorite layering pieces? Favorite types of material you’d recommend? Share them in the comments below and help each other out!

Also, if you want MORE ideas for how to layer (seeing these steps in action in more outfits), check out my blog post 5 Ideas for Layering + 13 Outfits for You to Copy!


Winter Starter Kit Wardrobe Guide

Want to feel put together this winter? Kick up your winter style with the Winter Casual Starter Kit Wardrobe Guide to learn how to bundle up while still feeling stylish and confident! Get the step-by-step plan to build a versatile winter starter kit wardrobe and learn to put it all together. You’ll be able to make 30+ outfits from just 15 pieces and do it while saving yourself time, money, and overwhelm! Check it out HERE.

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