20 Fall Boots to Rock in 2020

If I had a penny for every time somebody on the internet has celebrated that fall is almost here, I would have enough money to pay my rent for a month (and that’s a lot by NYC standards). I, on the contrary, am very sad we’re saying goodbye to summer. Just like Frank Ocean, I also get cold when the temperatures dip below 70s since my Caribbean self is used to 90-degree weather all year long. Sure, I’ve been in NYC for four years but four years isn’t enough time to figure out layering without looking like a marshmallow – at least not for me.

Layers might not be my thing. But the one thing I do like about fall (yes, there is a bright side to this) is being able to bust out all my boots. In Puerto Rico, you wear boots regardless of the weather. Yes, even if your feet feel like melted butter inside your socks. It’s just the cool thing to do! Here in NYC, it’s cool too but it’s actually practical. 

Plus, if there’s one thing that helps me feel put together once the temperatures drop it’s knowing that at least I have a few good pair of boots that will take me to and from my apartment to the city streets and still look (and feel) good. So, catch me switching out my chanclas for my trusty Dr. Martens and my go-to black, fall booties, while complaining about the weather soon!

Maybe you’re like me or maybe you are happily awaiting sweater weather, in any case: If you need to refresh your boot arsenal, we’ve rounded up the fall boot trends taking over your IG feeds.

Chunky Chelsea Boots

This season is all about practical footwear, which means you’ll be seeing lots of Chelsea boots and other iterations of comfortable boots. Like the ones below!

Circus By Sam Edelman Darielle Treaded Chelsea Boot


Urban Outfitters

Pull&Bear Short Platform Chelsea Boot



Leather Chelsea Boots

Black Calf High Chunky Chelsea Boot



Combat Boots

Combat boots are trending each and every fall — and we know exactly why.

Lace Up Combat Boots


Charles & Keith

Platform Boots

Dr. Martens Combs W Tech 8 Eye Boots



Topshop Bumble Lace-Up Bootie



Over-the-Knee Boots

Don’t picture over-the-knee boots with thin heels, remember this fall it’s all about being practical! So switch your heels for flat over-the-knee-boots. At first, you might get horse girl vibes, but we promise you, they’re trendy.

Thigh High Platform Boots


Charles & Keith

UO Sabrina Tall Boot


Urban Outfitters




Asos Design Kellie Chunky Over the Knee Boots



Rubber Rain Boots

Give it up for more chunky and comfortable boots to add to your roster.

Asos Design Glossy Riding Boot Wellie



The Rain Boot



Hunter Original Tall



Platform Boot

Snakeskin Boots

Love all the fall boots mentioned above but don’t want to go for the usual black booties? Then a snakeskin boot can be your new go-to!

Vegan Going West Boot


Free People

Pointed Heel Ankle Boot

Wedge Bootie



Coconuts by Matisse Spade Bootie



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