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Fall and Winter Footwear Guide

When it comes to winter shoes and winter boots, your footwear can, and should, be warm, functional and stylish - there is no need to compromise on any of it!

There's no question that there are a lot (and I mean A LOT!) of different types of shoes and boots available for fall and winter, and like the old Cheesecake Cafe restaurant menu, too many options can cause some confusion, am I right?

As a Stylist, I've been receiving questions like : What boots work with wide-leg jeans? What works with straight leg pants? Are ankle booties still a thing? What about sneakers and flats - how do they play in?

Let's unpack the Top Five Footwear Styles For Fall And Winter 2023/2024, plus a couple extra categories to make sure we check all of the boxes!

Ankle Boots

Considering that pant legs are wider than they've been in a long time and with colder temps ahead, ankle boots are a great fall and winter footwear choice! For a flattering, functional and warm option, look for styles that hit above the ankle bone and that fit snug around the leg. This will allow your your crop and full-length pants to fall smoothly over the boot but also keep your ankles covered and warm. (If you're looking for a great ankle boot that gives winter-warmth and style, I have great options for that below!)

Boots - Calf and Knee High

Tall boots are multi-functional : wear them with skirts and dresses, or with a slim pant tucked inside. If you'd like a pair to wear with pants, the boots should have a wide enough shaft opening for your pants to tuck in comfortably without feeling bunchy or tight (the only thing that should feel like a sausage is a sausage!). A wider shaft boot also looks great with your Fall and Winter skirts and dresses, so it's a great footwear option that gives you ultimate versatility, warmth and style! If you prefer a style that fits snug to leg to only wear with dresses and skirts, I have some great options for you too!


Thick, lug styles tend to add a lot of bulk & weight - making an outfit feel bottom-heavy. While this isn't necessarily a negative if you love the look, slim, streamlined sneakers gives a fail-proof, classic look that polishes off any outfit all year round. I do recommend staying away from the big trendy styles because in a year, they'll be dated.

White sneakers are always in style, but you might also want to consider something with multiple colours to add a little interest to your outfit, or a sneaker in a unique solid colour.

Ballet Flats

The Ballet Flat has been popular in Europe for years and it's now come to North America in full force and many are loving it! That being said, the style can have a tendency to look a little young, and to ensure you're rocking the look while looking polished, modern and cool, look for a toe shape that is a bit more squared-off and has minimal decoration. When it comes to wearing this style on the colder days, it really won't offer you much protection from snow or cold, but you can always wear a nice thin sock to give a bit more warmth.


Always a classic choice, a great loafer can go a long way! Look for a clean, streamlined style that doesn't go too long and pointed, or cut too high on the top of the foot (this elongates the foot - aka, makes feet look much bigger than they are). I do like that there are lots of options available for heel height, and materials (leather or suede) - there really is a loafer for everyone!

Winter Boots for Function & Style

If you live somewhere colder, like I do, a fall winter boot that offers you both style and function (aka- warmth) is important. There's nothing worse than cold feet when you're outside, and to help with that you will want a boot that offers a bit of insulation for both the foot bed and around the body of the boot.


When it comes to winter footwear and truly maximizing your winter shoes and boots, there are a couple of things that I can't recommend enough.

Taking care of your shoes ensures that they'll look better and last far longer, and why not take care of the things you invest in?! The most important step is a good shoe protector spray or lotion - something that will repel both water and salt (two things that can really damage any materials and make them look terrible). I've been told by shoe experts that you should protect your footwear every 12-14 wears. But you also need to make sure that your winter footwear is clean before you spray, and that means removing not only dirt and dust, but any salt or water stains as well. A great wipe can do all of that for you!

The next thing is one of my personal favorites - a warm, cozy, wooly insole. These make all the difference for those cold days - I don't know about you, but cold pavement cuts through right to the feet and causes a full-body chill that I just can't shake! Going for a winter-combatting insole will insulate your feet and keep them warmer and dryer for longer, no matter what style of shoe or boot that you're wearing!


As I said, when it comes to winter shoes and winter boots,

your footwear can, and should, be warm, functional and stylish,

and I hope this shows you that you truly don't need to compromise!

If you see something you like here, every image is linked directly to the stores that I found them at to make shopping easier for you!



It's not all about my love for fashion and passion for helping men & women feel their best. From my family, to love for creating a home that everyone feels comfortable in, and the pull to always be near the water (which is tough when you live in the prairies)...



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