Must-Have Shoes for Fall and How to Style Them

I’m going to hold your hand when I tell you this, but your choice of shoe can literally make or break your fall outfit. I don’t want to scare you, it’s not Halloween yet! But don’t worry, the right shoe will step up your style game faster than you can say pumpkin spice, and you’ve come to the right place. I’ve rounded up all the trending shoes for fall, and even created some outfits for inspiration on how to style each. Aren’t you happy you found a stylist?

  1. Ballet Flats - more specifically, Mary Jane’s

Mary Janes are all the rage right now, and for good reason. They’re cute, chic, and add a feminine touch to any outfit. Whether you're pairing them with skirts, jeans, or dresses, they work seamlessly with so many looks. As the weather cools down, you can wear tights, but the real style fun comes with your socks. Think frilly ballet socks—yes, just like the ones you had when you were 5! We’re bringing them back, and they’re just as adorable as ever.

See below for my picks of flats:

*reminder, just click the image of the item you love and it’ll take you right to the site for easy purchasing.

2. The Boot, of course

Boots are a fall/winter staple that never go out of style. Honestly, one of the things I look forward to most when the weather cools down is breaking out my favourite fall boots! This year, the classic tall boot is still going strong, but we’re also seeing a big comeback of equestrian-inspired rider boots. It's such a cute, fresh take on a classic. I actually have a gorgeous pair of riding boots from Roots that I got back in Grade 11 (if you know, you know), and I had to get my mom to mail them to me from Winnipeg because I need them back in my rotation!

We know boots go with so many fits, so if you’re in the market for a new pair, see my below picks;

3. The Pump (tini) … Vanderpump Rules reference lol

When I say my black pumps were my most-worn shoe last fall, I’m not exaggerating. My slingbacks are so worn out that I need a new pair—the satin is literally falling apart! I know what you're thinking: 'Maddi, why didn’t you invest in good quality pumps?' Well, reader, I DIDN’T KNOW THEY WERE GOING TO CHANGE MY LIFE! It started as an experiment, and now I’m in a full-blown love affair. So, I’m here to tell you—you need a pair of pumps this fall. If you want to add a little pop to any outfit, just throw on your pumps. I promise you, they’ll do the trick.

See my below picks for pumps:

4. Sneakers, obviously! But with a twist.

If you haven't bought a pair of 'fun' sneakers yet, this is your season! I know they can feel intimidating, and you might wonder how many outfits you can pair with such bold colours. But I promise, it’s more than you think. Personally, I love the silver option because it goes with greys, reds, blues, blacks—the list is endless! You can also swap the grey outfit above for the leopard print sneakers (you already know how much I love leopard print). The Adidas Sambas and Gazelles are still very much in style this season, and they’re incredibly comfortable. I own a pair of red Gazelles that I’ve worn into the ground, and I still have so many fall outfits I can’t wait to pair them with!

Let’s have fun with our sneakers this fall. See my picks below:

That’s all for now! I hope this round-up was helpful for your fall shoe shopping. If you’ve got any questions on sizing, different styles, or if you’re curious about the pieces I created the outfits with, message me on Instagram: @maddisoubry.

Talk soon!

Mads

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Looks for Less - The Pre-Fall Guide

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Fall 2024 Fashion Trends - Animal Print