Styling Boots for Winter
how-to
It’s time — time to pull out the boots! Depending where you live, it probably changes what boots you’ll be styling this winter. I’ve pulled out three pairs of boots to style for this segment. These boots help me transition from fall to deep winter. Alright, let’s get into it!
The Boots
A classic pair of rain boots - I’m styling the Classic Black + White Ankle Rain Boot from Alice + Whittles. These are the perfect rainy day boot that seriously go with any outfit because they are so simple and have such a classic look. I’ve worn these around town and also on light hikes and they’ve held up very well keeping my feet dry and warm.
The elevated ankle boot - I’m styling the Town Boot from Dear Frances. These are literally a dream to wear! They are so slim and beautifully crafted with the most flattering soft square-toe silhouette. They feature a comfortable heel and delicate panelled sides. These have been my go-to pair of every day boots.
The weather-defying combat boot - I’m styling the Phoenix Lace Boot from Sorel. I bought these last year to replace an old pair of winter boots that came to the end of its life. These held up pretty well in the Toronto snow and keep my feet feeling snuggly and warm throughout the winter.
Outfit #1
Striped Top: old Muji
Denim: Nina Wide-Leg Jean, Frank & Oak
Look number one is made for those light, rainy fall days — complete with wardrobe staples like a striped long sleeve shirt and a pair of wide leg denim. Pop on a fleece jacket and some classic rain boots for the perfect casual rainy day outfit.
Outfit #2
Sweater: Modern Fisher Cotton Sepia, Tradlands
Denim: Abigail Crop, Outland Denim
Jacket: RAINS
Rain Boots: Classic Black + White Ankle Rain Boot, Alice & Whittles
This outfit is for those cold rainy days when you just want to stay snuggled in bed. I’ve tucked a classic fisher knit into a pair of black skinnies, along with cozy socks. To complete the look, I went full on with the rain gear — rain jacket and rain boots to make for the perfect waterproof outfit!
Outfit #3
Jacket: Aritzia
Boots: Town Boot, Dear Frances
If you know me, you know I love timeless, classic outfits. This outfit is something I can see myself wearing season after season. I’ve styled these ankle boots with a pair of straight leg jeans and a chunky, oversized black knit. This is my kind of go-to outfit during the colder seasons. I mean, who doesn’t want to snuggle up in the coziest sweater while sipping on a cup of hot coffee? For the outerwear, I’ve gone with my oversized wool coat that gives it a pop of colour while keeping the sophisticated feel of the outfit.
Outfit #4
Turtleneck: old UNIQLO
Denim: High Rise Pant, Tribe Alive | Use Candice15 for 15% off!
Jacket: Aritzia
Boots: Town Boot, Dear Frances
Continuing on with the classic outfits, lately I’ve been experimenting with lighter denim for fall/winter and have been loving it! It adds another dimension to an outfit and a sort of airy, lightness to outfits that would typically be weighed down by heavier knits. In this outfit, I’m playing with contrast. Contrast in colour as well as with silhouettes. I really enjoy the dramatic feel of the black turtleneck against the beige pants and the form fitting top with the wide-leg bottoms.
Outfit #5
Turtleneck: old UNIQLO
Denim: old Cheap Monday
Belt: Frank & Oak
Puffer: ReNew Long Puffer, Everlane
Boots: Phoenix Lace Boot, Sorel
The final pair of boots I’m styling are my winter snow boots. This is an outfit I often sport during the winter because it’s simple and easy to throw on in the hustle and bustle of a busy morning. This outfit has a slimming silhouette with the black turtleneck and high waisted mom jeans, cinched at the waist with a minimalistic circle belt. The combat-style boots add a bit of edge to an otherwise “plain” look. For this wintery look, a puffer jacket is the way to go!
Outfit #6
Sweater: Oversized Alpaca Crew, Everlane
Denim: Abigail Crop, Outland Denim
Toque: me-made hat!
Puffer: ReNew Long Puffer, Everlane
Boots: Phoenix Lace Boot, Sorel
This final outfit features the most gorgeous alpaca wool knit tucked into a pair of black skinnies. The combat boots continue the line of the black skinnies, making my legs appear longer than they are. This helps to elongate the body and is a simple styling hack for anyone looking to add a little height to their outfits! I “topped” off this look with a me-made toque and a puffer for my final deep freeze outfit.
That’s it from me! I hope you enjoyed these wintery outfits and little tips along the way for styling boots this season. Maybe it’s given you a bit of inspiration. I’d love to hear your thoughts — let me know which outfit was your favourite! Is there one that you want to try out this season?
This post is not sponsored but contains some gifted items and affiliate links. If you decide to shop through the links above, I make a small commission that helps support this blog and my Instagram. I only share products and brands I love and support. All opinions are my own. Thank you for supporting Candice Tay!