My Favorite Winter Gear to Survive Chicago Winters

Winter in Chicago is no joke. And even though it’s practically March, spring won’t be here for quite some time. So I figured it was still appropriate to chat about my favorite winter gear and how I’ve been surviving the crazy weather lately. Like that -25 degree day we had in early February? Holy smokes. Absolute chaos!

My Favorite Winter Gear


My favorite winter gear to survive Chicago

Jeans // Jacket // Boots // Sweater // Hat (from Quebec City) // Socks

Since we live in the city, both Finn and I walk practically everywhere. We rarely use our car…usually just to head to the grocery store or when I drive out to Bridget’s house in the suburbs. And because we walk everywhere, we have to bundle up every time we head out the door. So while I appreciate looking cute during the winter months, I’m much more focused on being warm when I’m out and about.

If you’re looking for new winter gear this is actually the perfect time to stock up. Spring clothing is coming out in full force, so a lot of stores are getting rid of their winter inventory. You can save a lot on jackets, boots, and other winter accessories right now…so hopefully this post serves as a good reminder!

Winter Coat

Puffy winter jacket for Chicago winter

A puffy coat with a hood is an absolute must. You really can’t survive a Chicago winter without one. I’ve had a lot of success buying winter coats from Nordstrom Rack in year’s past, but my latest jacket is this one from Macy’s. I got it on super sale and it’s great! Super warm, has a hood, goes down to my knees, and is pretty lightweight! Plus, I love the gold detailing.

 My favorite winter gear including this puffy jacket

I also like that it’s a bit tailored, yet roomy enough to wear bulky sweaters underneath. Bridget loves her North Face jacket and I debated getting that one. I even headed to the store and tried a bunch of different styles on. But I couldn’t find one that I absolutely loved for the price. I’m happy I found this one instead!

Finn wearing a winter coat from North Face

Finn actually got this North Face coat for Christmas and he is obsessed. I put it on and it feels like you’re wearing a down comforter. It’s so warm and thick. He ventured to work on one of the -10 degree days earlier this month and said his body was perfectly cozy in this coat. If your guy needs a new one, I highly recommend this winter coat!

Winter Boots

While we get a lot of snow here in Chicago, you’re almost always dealing with salt and slush. Which is disgusting, dirty, and so damn messy. I really don’t mind the cold, but the dirty streets and slushy snow is by far my least favorite part about this time of the year. Sorel boots for winter

Quality winter boots are a must and I rarely wear “real shoes” during wintertime because they’ll inevitably get destroyed. I got these Sorel boots (currently on sale!) from my mom for Christmas and I think I’ve worn them every single day since. Sorel boots for the snow

I wore them on repeat during our Quebec City trip and have walked miles and miles in them. They’ve definitely gotten dirty, but I’ll occasionally take a wet rag and wipe them down and they look good as new. My sorels rarely go on sale, so I’d say now is the BEST time to buy!

I purchased these Ugg boots last year and love them too. I don’t wear them as often as my Sorels, but the Uggs are nice when I don’t want to wear big clunky boots somewhere. They’re a little less noticeable if you know what I mean.

These booties (similar)are also a winter must-have for me because they’re water-resistant! I opt for these when I’m going out for date night or need to get a bit more dressed up during the winter time. I’ve had them for 2 years now and they still look great. I just use the same wipe down method to get any excess salt or dirt off and they stay looking just fine. I just saw my friend in these cute wedges (that have killer reviews!) and they’re now on the tippy top of my wish list. Love that they’re stylish, yet good for the yucky weather.

Warm Winter Socks

Wear warm socks underneath boots

I talked about these winter socks in our Quebec City recap post, but holy smokes…I’m a convert. Yes, they’re expensive but they are worth the price! On super cold days, I only reach for these socks and my feet never get cold. You certainly don’t need to replace all of your socks with these ones, but just having 2-3 pairs on hand will help you get through winter with ease.


My favorite winter gear

Finally, let’s chat winter accessories! I keep a big basket in my closet with all of my scarves, hats, and gloves and try to switch things up when I remember. But to be honest, I usually just wear the same items on repeat because they’re in my purse or in my winter coat. My favorite winter gear

So many of you guys have asked about my white winter hat and my buffalo check scarf. Sadly, they’re both old items (scarf from LOFT, hat from Old Navy), so I don’t have links for them (although this hat is super similar!) I also picked up a new gray winter hat from a little shop in Quebec City and that’s been my go-to hat this winter season.

As for gloves, I’m all about leather gloves. They look polished, aren’t too bulky, and many of them have the touch technology so you can still use your phone! These ones (no longer sold) were a favorite from our gift guide, but I like these ones too. The best part about leather gloves is that they can last for years, so I’m all about investing in a nice pair (especially if you live somewhere cold like Chicago!). I also love a good “glitten“…or perhaps I just like saying the word glitten.What to wear for Winter in Chicago

Spring is officially only a few weeks away, so let’s hope things start to warm up soon. Even just a little more sunshine would make me happy during these dreary days!


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.