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.
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:
ShopWilew Vintage '90s Leather Knee High Boots ($171)
Someone buy these babies before I do.
Jeffrey Campbell Maximal Knee High Boot ($275)
The proportions are perfect!
Zara High Heeled Leather Boots ($229)
It's giving mod princess.
Alohas East ($350)
Ready to run through a pile of fall leaves.
Louise et Cie Yancey ($229)
The buckle detail and heel shape add so much character.
Staud Wally Suede Knee Boots ($495)
This gorgeous suede elevates any outfit for real.
Miista Finola Boots ($670)
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:
Miista Minnie Boots ($520)
These are simply the coolest.
Manu Atelier Duck Boots ($605)
Manu always gets it right.
Eytys Gaia Leather Boots ($500)
I'm obsessed with Eytys right now.
ASOS Design Rosa Heeled Ankle Boot ($111)
This muted blue feels so Spanish to me.
Who What Wear Collection Christina Boot ($149)
Replace your 2019 pointed-toe white booties with these—trust me.
Camper Karole Bootie ($240)
Camper is known for having the most comfortable shoes, so I know these are everyday-worthy.
Rick Owens Sliver Chelsea Boots ($1740)
Rick, Rick, Rick, Rick.
Vagabond Shoemakers Edwina Square Toe Boot ($225)
Straightforward everyday boots. These will go with everything.
Public Desire Rae Pull On Boots ($56)
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:
Mango Elastic High Heel Boots ($120)
Who needs leather pants when you can have these?
Zara Cowboy Leather Heeled Ankle Boots ($129)
Love these with jeans and a simple top.
Mango Pointed Heel Ankle Boot ($60)
Prepare to break some necks.
Neous Square-Toe Leather Boots ($1059)
The kitten-heel square-toe combo will never go out of style.
Vintage and Heirloom '90s Leather Kitten Heel Ankle Boots ($25)
I had to do a double take at the price. Wow.
Mango Heel Leather Ankle Boot ($150)
Tantas curvas y yo sin frenas.
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:
Frye Campus 14L Boot ($328)
The perfect gardening boots.
E8 by Miista Malene Mid Boots ($335)
These are inspiring me to go to Madrid.
Durango DB510 ($162)
Everyone in pointed-toe cowboy boots will be jealous of you in these.
Peter Do Squared-Toe Combat Boots ($572)
Oof, this color reminds me of the galaxy. Plus, they're 50% off right now.
Paris Texas Roxy Boots ($980)
Tinacus Leather Square Toe Boots ($129)
These zip up in the back so you don't have to untie them.
ASOS Design Chilli Harness Knee Boots ($54)
Can you kick it? Yes, you can.
This article originally appeared on Who What Wear
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