Best Tall Boots for Cold Weather

Pink Ruffle Sweater | White Tassel Scarf | Faux Leather Leggings | Black Suede Over the Knee Boots | Grey Crossbody Bag | Black Sunglasses

If there’s anything I learned from moving to Chicago, it’s that cold weather gear is essential. Things like boots are not only fashionable but also functional. And every girl in the Midwest, east coast, and Canada needs this arsenal of boots to get her through winter.

Having a well rounded collection of tall boots is like having a makeup bag with everything from concealer to mascara in it. Each item in your makeup bag serves a very distinct purpose. Just like each boot in your closet does. While the news that you need more than one tall boot to get through a season may come as a shock, I’ve narrowed down the list to my top 5 and they’re all from Nordstrom. You guys know from my posts here and here last month how much I shop at Nordstrom! Especially for the colder months – they have such a great variety that it makes things so easy for you!

Trust me, a year ago I knew none of this. What boot is going to keep me warm in sub zero temperatures? What is easiest to walk through snow with? How can I stay warm but also look cute? Those were all lessons that it took a Chicago winter to teach myself. With the 5 boots that I’ve picked today, you can survive anything Mother Nature throws at you. Yes, all of these (or a version of them), need to be in your closet. If you have more than 5, lucky you!

Cute daytime boots. 

It’s bitter cold outside but you’ve got plans with the girls for a weekend brunch. While everyone else may be content to snuggle up inside, girl time is a must have. So how do you show up stylish but also keep yourself protected from the biting cold? These suede over the knee boots.

Over the knee boots are the best kept secret for warmth. With some thick cozy socks underneath, you’ll be surprised at how warm you’ll be. Unless the weather is particularly treacherous, you can get away with pairing these with a sweater dress. If it’s grim outside, pull them on over your favorite skinny jeans. You can’t go wrong with these slouchy beauties. The best part is they come in 4 colors and are 33% off right now!

Don’t love a boot with a heel? The flat version of this boot also happens to be 33% off and comes in four colors. I have the heeled version on “Foxy” and the flat version in black. I walked to work in the flat boots last week and felt like they were pretty comfortable. Just size up a size if you have wider feet!

Night out or date night boot.

Sometimes, the thought of all the layering you need to do to go out is too exhausting and you end up binge watching Stranger Things on the couch with bae instead. Other times, you brave it. If you’re smart, you wear these suede over the knee boots. They keep you warm without having to sacrifice style. Again, layer these over thick socks to keep you cozy!

My favorite way to wear these is over my faux leather leggings. It’s so easy. You can wear almost anything on top and get away with it. That said, you can also wear them with denim, dresses (see here for inspiration), or with skirts. I’ve gotten a ton of questions lately if OTK boots are appropriate for the office and they are! Keep watching my OOTDs on Instagram Stories for more work outfit inspiration!

I have these OTK boots in black (first purchased last year). They have survived a full year already and I’m going to wear them again this year. I also recently got the grey suede version because I love them that much! They stay up better than Stuart Weitzmans and are a quarter of the price! Size up if you have wide feet or wider calves!

Errands and workout class boots. 

I didn’t appreciate the need for this type of boot until halfway through winter. I tried to wear my snow boots. I tried to wear my hunter boots. But both were such a hassle to get off and put back on that I had to find a solution. In come UGGs. While they vaguely remind me of high school, I’ve opted for different colors like this grey pair to keep things in 2017.

UGGs and similar pull on, shearling lined boots at Nordstrom are incredibly warm. They’re so easy to get on and off you can almost do it without your hands. And when I’m trying to unzip a giant puffer coat, unwrap my thick knit scarf, and not knock anything over in the meantime, it’s a must. Plus, they’re really comfortable so I’ve even slipped these on for my walk to work and changed into my favorite work pumps when I get to the office!

Just walk with caution when there’s snow out – the grip on the sole isn’t the best. Which brings me to my next boot!

Walking in wet conditions.

Hunter Boots are in every girl’s closet for a reason. Yes, they’re adorable but they’re also functional (yay!). I have two pairs – the Original Tour in green and these in grey. Between these two colors, I can wear Hunter Boots with almost everything in my closet. Browse my Ireland photos for more outfit inspiration. You’ll be surprised how versatile they are!

Rain boots are obviously for rain but what I didn’t realize was that it translates to the snow too. I wear Hunters all throughout winter here in Chicago in my walk to work. I put a thinner athletic sock under my Hunter Boots socks if I plan to keep them on all day. Otherwise I put on a thick knit socks for the walk and take everything off once I get to my desk. The grip at the bottom is sure to keep you from slipping and you needn’t worry about all the salt on the ground because they can easily be wiped down. They are best for temperatures above 20 degrees.

Tip: wear Hunters on your way to work and swap them out for either of the suede boots above once you’re in the office! Also, all of the below colors are on sale right now in the Nordstrom Fall Sale!

Hunter Boots run true to size but if you have wider calves, size up a full size.

Snow boots.

There are times you can get away with Hunter Boots and there are times when you need to break out the heavy artillery. While the scene outside may look more grim than the Grim Reaper, good snow boots can be the silver lining. The best boots are SORELs. The quality is incredible and they’re the only waterproof boot I’ve found that is still cute.

Did you know that even rain boots aren’t usually waterproof? That’s why your feet will often feel cold all day or slightly damp when you take them off. That’s fine for slightly warmer weather but when it’s brutal outside, I’m not taking any chances.

The Joan of Arctic boots are the best darn boot there is. They’re very thick, double lined, and embellished with a little fur. If you’re heading to the mountains for a ski trip, pack these. I wear them on the ugliest days here in Chicago during my walk to work or around on the weekends if I know I’m going to be out for a while. Just note that you’ll walk slower since there’s so much protection on these boots so give yourself a little extra time. They run true to size but if you are in between sizes, size up.

Here they all are rounded up!

There you have it! This is my winter arsenal of boots. I have all 5 of these in my closet now so I know I’ll be set for winter this year. Each one truly serves a different purpose and is necessary for one type of weather condition or event. Between all 5 though, I can’t think of anything where at least one of these boots wouldn’t be appropriate!

*In partnership with Nordstrom.