This Ankle Boot Trend Will Be Everywhere Come Fall...but We’re Planning On Wearing It Now

PureWow editors select every item that appears on this page, and the company may earn compensation through affiliate links within the story. All prices are accurate upon date of publish. You can learn more about the affiliate process here.

chunky sole boots
Jeremy Moeller/Getty Images

Raise your hand if you’re so happy comfy footwear is trending *raises hand.* While we’ll be wearing dad sneaks and grandma shoes for the foreseeable future, we’re adding one of September’s biggest trends to the rotation: chunky sole boots. Yes, these ankle boots were technically spotted on the fall runways from cult-favorite labels like Gucci, Alexander McQueen and Tibi, but we’re making room for them on our spring shoe rack immediately. Who says we can’t wear them now with flirty dresses and later (when they’re nice and broken in) with cropped jeans and an oversize sweater? Here are eight pairs bound to become our favorite year-round shoes.

naturalizer boots

Naturalizer Luna Chelsea Waterproof Booties

Wear these on rainy spring days.

gucci boots

Gucci Trip Jewel Strap Bootie

Comfortable and fancy is our favorite combination of words.

jeffrey campbell1

Jeffrey Campbell Lug Platform Bootie

Side cutouts make this pair very appropriate for spring.

doc martens boots

Dr. Martens Quad Chelsea Boots

Just as comfy as the traditional lace-up version, but in an easy pull-on style.

topshop boots

Topshop Ashton Chain Moto Boot

The classic combat style has been elevated with an extra edgy touch.


Loewe Front Zip Bootie

Linen and cotton uppers keep these breathable, while a lug sole makes them super walkable.

3 1 philip lim
Saks Fifth Avenue

3.1 Phillip Lim Lela Leather Booties

Part sneaker, part bootie, 100 percent on-trend.

Moda Operandi

Proenza Schouler Patent Leather Chelsea Boots

We want to live in these from now until…forever?

BL Headshot


Brianna Lapolla formerly held the role of Senior Commerce Editor at PureWow covering all things shopping across beauty, fashion, and lifestyle. Now, she's putting her 12 years of...