A Winter Shoe Guide

January 4, 2021
Sara in a winter outfit with Sorel Boots

Although this winter may have us spend more time indoors, we feel that in order to be #justliving, you need a pair of warm, water resistant, comfy shoes to get you through any winter.  More specifically, we feel that when it comes to winter shoes there are some that are worth the investment for not only practical reasons but for your well-being so that when those temperatures drop your footwear is not holding you back from enjoying whatever outdoor activity suits you. Plus, if you are anything like us you can wear these shoes indoors to keep your feet comfy and supported. This is our guide that will hopefully provide you with a range of styles and levels of comfortable, cozy, and water resistant shoes that are investment worthy. 

Sidenote: most of these shoes are tall girl approved, meaning that I (Maddie) was able to find all of these shoes in a size 11! I have also seen Blondo, Sorels and Uggs in size 12 too!

Ugg Slippers

Okay so maybe these aren’t technically shoes and are to only be worn in the home but hey we did mention this winter is different from the rest and that is why this is first place on the list. These ugg slippers make you want to never have to wear formal shoes another day in your life, they are heavenly and oh so warm. If any year they are worth the investment — it would be this year.


Ugg Declan Boot

So another pair of Uggs? Yes, pick your poison, both are amazing. Now I will be transparent these are not as warm as the typical pair of uggs, but I find that to be okay knowing that these are more shoe material than traditional ugg look. I style these with some fuzzy warm socks (shoutout to target 1 dollar special in the stocking stuffers) and wear them underneath, as a result I have never had a day where I was left wanting to revert back to the traditional uggs. These are so cute and I have gotten a wide range of comments all good about these from women of all ages. I think it’s safe to say if you want Uggs that are a cute style this is the new update we have all been waiting for.


The Glenda Blondo Shoe

These are so cute and better yet they are comfortable, warm (enough, not going to be the same as Uggs, of course) and technically water resistant. Now I would never wear these on a snow day because well they are wedged and I would for sure fall and eat dirt and I try to limit that to once per winter at most. These are the cute sneakers you can sport with jeans that dress it up more than Uggs but not a dressy evening type of wear, which honestly this year is probably the most ideal. These were perfect for when I lived in Boston and nights out didn’t call for the dressiest wear but I still wanted to look cute. Also Tall girls important note: this is also a great way to feel like you can sport a slight wedge and not add five inches (if you aren’t wanting to be the tallest in the crowd– obvi nothing wrong with that either!) Furthermore, they come in extended shoe sizing of 11-12. This brand is great for those girls that have trouble finding their shoe size.

Maddie at the beach with sorels on

We both love this brand when it comes to winter boots!


Of course if you are from the north you have heard of these before. There is a reason this brand does so well and that is because they are practical in that they provide very warm, water resistant shoes. Their boots are a great staple shoe to get you through any winter storm. They have sooooo many styles which is great too if you are from a region that isn’t entirely freezing but may get the occasional snow storm that shuts down the entire city for a week (every northeasterner is LOLing at this but we understand snow and driving can be scary). For milder climates a shorter boot can cover you for winter commuting in rain, slush, or snow! 

Santana Canada Waterproof Boot

So I just discovered these amazing boots and let me just say with utmost certainty, that these amazing boots are worth the investment if you live in northern regions where you are bound to experience snow and frigid temperatures for at least a few months every year. Honestly, it wasn’t until I tested these out that I realized there is the possibility for snow boots to give you the support of a regular shoe.  I can’t begin to explain the comfort of these as I’ve seriously never experienced boots with this much support.  As someone who has knee problems, the support was instantly evident and it felt like I was walking on an absorbent platform that was taking the full impact and force so that my knees weren’t feeling any discomfort in the slightest. Plus these are just plain cute.