Transitional Trends: Taking Your Shoe Collection from Fall to Winter


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Chances are, you’ve probably already retired your sandals from the summer. Those chillier temperatures mean you’ve opted for a closed toe, and maybe even started to bring out the boots. As we look ahead to the winter months and even start thinking about holiday parties, we’ve got some recommendations for footwear that you can keep in your wardrobe from fall, and a few new options that will get you through the cold. 

1. Slouchy High Boots

The high boot has been a trend that’s come and gone in past seasons, but for winter they’re back in a big way, but this time a little slouchier. Keep it simple with a solid colour and texture, but look for some volume in the material to achieve that perfectly slouchy look. 

Shoelistic, Toni Tall Boot, $369

2. Pointed Toe

Whether as a flat or a heel, gone are the squared toes from past seasons. The pointier the better. Look for a sharp point to achieve this trend and have fun with material, embellishments, and height of heel. 

Aldo, Carlita Kitten Heel, $69.98

3. Wedges

That pointy kitten heel that you kept getting stuck in the grass at garden weddings? You can still wear them this season, but you may want to reach for a wedge to help you navigate the winter streets. These more pragmatic heels are great for the office to the holiday party and can offer some interesting structural looks. 

Bloomingdale’s, Jeffrey Cameron Wedge Heel Bootie, $229.00

4. Lace/Buckle Up Boots

The punk rock look is making a comeback in a big way. While your lug soles from fall are still very much on trend, we’re seeing the look evolve with laces and buckles. Pair with a grunge-rock look, or add some interest to a more feminine outfit with combat boots.

Bloomingdale’s, Shutz Georgina Triple Buckle Boots, $94.60

5. The Little Black Pump

Last holiday season we saw lots of glitter and embellishments on heels—remember the quintessential crystal broach on the toe of everyone’s favourite party pumps? Well this year, the classic black pump is all the rage. Chic, streamlined, sleek, black, and completely devoid of embellishment. This winter, the pump is all about quiet elegance which makes it a very easy trend to hop on. 

Aldo, Cassedyna Pump Heel, &79.98

6. House Shoes

It seems the p*ndemic brought with it a comfort trend that has… never left? And we’re here for it. Hygge is in, in all it’s glory this winter and the easiest way to hop on the trend if you haven’t already is with the slip-on clog. Think of it as a more structured slipper. 

Bloomingdale’s, Birkenstock Boston Clog, $142.00

Looking for more winter footwear inspiration? We’ve got you covered. Check out our picks for stylish winter shoes. Happy shopping!

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