If you look through the annals of boot history, right behind the pointed-toe shoe stands her stepsister, the square-toe. Instead of fighting for the spotlight, square-toe is comfortable in the shadows of her popular sister. In fact, she has created her identity there—it’s actually what makes her cool. Those who wear square-toe shoes do so because they identify with that energy. To me, square-toe boots look a little bit grotesque in the absolute best way. They aren’t pretty in the conventional sense and call us to dig a bit deeper to see their beauty, which is precisely why I am drawn to them.
This fall, square-toe boots have arrived in every shape and style from ’60s mod to ’90s sitcom, space cowgirl to witchy. Keep scrolling to find the best pairs for every price point across the internet. Your new bestie boot is waiting for you.
Knee-High Boots
Between the '60s go-go boots and the miniskirt, this outfit feels so California flirty-cool. Knee-high boots look great with all the micro-minis that are currently trending and provide the retro vibes I'm seeking to re-create this fall. These boots also look great under midi and maxi dresses and skirts in a bohemian way. The possibilities are truly endless.
Shop knee-high boots:
Someone buy these babies before I do.
The proportions are perfect!
It's giving mod princess.
Ready to run through a pile of fall leaves.
The buckle detail and heel shape add so much character.
This gorgeous suede elevates any outfit for real.
Texture, honey.
Ankle Boots
Square-toe boots peeking out from under a pair of pants is the perfect final touch for an otherwise simple outfit. Brands like Miista, Vagabond Shoemakers, and Eytys have made a name for themselves from this shape and have kindly expanded the options for us all. You'll want to make room for a pair or two of this shape alone—the lineup is that good.
Shop ankle boots:
These are simply the coolest.
Manu always gets it right.
I'm obsessed with Eytys right now.
This muted blue feels so Spanish to me.
Replace your 2019 pointed-toe white booties with these—trust me.
Camper is known for having the most comfortable shoes, so I know these are everyday-worthy.
Rick, Rick, Rick, Rick.
Straightforward everyday boots. These will go with everything.
Where are my space cowgirls at? Also, this wedge situation is so cute.
Pointed Square-Toe Boots
Being that we are currently in a cultural renaissance, it's appropriate for the pointed square-toe boots to also be making a resurgence. I'm loving the drama of this shape, which harkens back to the Marie Antoinette days. Showcase its evolution by baring plenty of leg and mixing in different stylistic inspirations to create something brand new.
Shop pointed square-toe boots:
Who needs leather pants when you can have these?
Love these with jeans and a simple top.
Prepare to break some necks.
The kitten-heel square-toe combo will never go out of style.
I had to do a double take at the price. Wow.
Tantas curvas y yo sin frenas.
Flat Boots
Last but not least is the earth sign of the bunch: sensible flat boots. Frye has been deep in this bag since its inception, and other brands like Durango and Paris France are making this shape a staple of their own. I love seeing these boots paired with lighthearted pieces, as pictured, to balance the groundedness of the style.
Shop flat boots:
The perfect gardening boots.
These are inspiring me to go to Madrid.
Everyone in pointed-toe cowboy boots will be jealous of you in these.
Oof, this color reminds me of the galaxy. Plus, they're 50% off right now.
Badass.
These zip up in the back so you don't have to untie them.
Can you kick it? Yes, you can.
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The $140 Boots London Fashion Girls Take Out of Storage Every Summer to Wear With Shorts and DressesFrom Kate Moss to Daisy Edgar-Jones.
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Return Those New Flats—*These* Are the Cool Shoes Fashion People Are Wearing With Dresses and SkirtsFresh and unexpected.
