Comfortable, versatile, and rugged, the bootie can do it all.
As we relish in the final days of summer, we can’t help but let our minds drift to fall. Nothing makes you yearn for crisp breezes and warm mugs of apple cider more than summer weather that’s so hot you fear you may actually melt if you step outside of an air-conditioned space. While we’re waiting for fall to arrive, we’re also starting to plan our transitional outfits, paying special attention to our shoes.
Booties, or shooties (try and say that without giggling), were created in the early 1800s out of necessity. Women needed a shoe that was comfortable enough to wear while running errands, but it also needed to be feminine and beautiful should they peek out from beneath a hemline. Made from materials like silk or satin, they weren’t the most practical shoe (despite literally being invented for practicality), but they bridge the gap between heeled shoes and riding boots, so at least there’s that.
While we’re still wearing booties to run errands, we’re also wearing them for just about anything else. If you want to get technical, booties are any boot that stops around the ankle or just above it. Anything higher than the ankle is considered a regular boot, although we know that we just use whatever body part the boot shaft ends at to describe the kind of boot we’re wearing (e.g. knee-high boots, ankle boots, thigh-high boots).
Consider that your free history lesson for the day. Let’s cut to the chase, though: Booties are a versatile style of shoe that should be in every woman’s closet. You can wear them during the last few days of summer into the breeziest days of fall — they won’t make your feet sweat on hot days and will keep your tootsies warm on colder ones. Here are some of our favorite booties to wear during the transition from summer to fall and all the way into winter, all of which are extremely comfy.
11 Best Ankle Boots and Booties for Women
Nisolo Heeled Chelsea Boot
Nisolo
If you’ve sacrificed comfort for style, the time has come when you can have both. These heeled boots have an extra cushy insole to ensure the balls of your feet don’t ache after a few minutes of walking, and they’re made from durable leather, so you can wear them for years. One reviewer noted that they “feel sexy and comfortable when wearing these. HUGE WIN!” It’s a win in our book, too.
Dr. Scholl’s Lawless Western Bootie
Nordstrom
Dr. Scholl’s used to bring to mind orthopedic shoes that were definitely comfortable, yet not so stylish. In recent years, the brand has certainly upped its style game without forgetting its roots of making extremely supportive and cushy shoes. These Western-inspired booties have a lower heel so they’re easy to walk in, and the toe is only slightly pointed, so it won’t squish your feet while you wear them.
Blondo Tasel Waterproof Block Heel Bootie
Nordstrom
We’ve all worn (and risked ruining) beautiful heeled boots on rainy or snowy days because they were the pièce de résistance of an outfit. Thankfully, these leather booties are already waterproofed, so you don’t have to spend time spraying them with a waterproofing agent and trying not to suffocate in the process. This pair has a simple silhouette and walkable stacked heel, making it a sleek addition to both dressy outfits and casual ones.
SOREL Emelie II Zip
Zappos
If you find yourself doing any sort of travel this fall, pack these boots. They have a flat sole so your feet won’t hurt after a day full of walking, they’re weatherproof for whatever mother nature throws at you, and they zip on and off so you won’t hold up the security line at the airport before you go through the metal detector. They come in gray, black, and brown, so you can pick whatever your favorite neutral is.
Everlane Glove Boot
Everlane
Those with either wide or narrow feet can have trouble finding shoes that fit right, but these are made to fit like a glove, literally. Instead of leather or canvas, these booties have a stretchy sock-like material as the base, so your feet are gently hugged while you wear these. They have a sleek look because they are so fitted around your foot and ankle, which reduces any possible blisters from rubbing.
Marc Fisher LTD Mlhenley Western Chelsea Boot
Saks Off 5th
Apparently, #cowgirlcore is a thing now? We can’t keep up with all of these new TikTok style trends, but we’ll try our best. Embrace your wild western side with these cowboy-inspired booties. They have a chunky heel for easy walking, and a blingy chain on the front gives it a bit more of a glam feel than a farm aesthetic.
Aerosoles Simple Boot
Aerosoles
Just as the name implies, this easy-to-wear boot has a simple shape that’ll go with just about anything. A slight slouch makes it easy to tuck pants or leggings into the boot shaft without either bunching up, and the lack of a heel makes these great for everyday wear.
Madewell Rayna Lace-Up Boot
Madewell
Remember the rugged combat boots of the ‘90s? These are her refined older sister. Made from sleek leather, these lace-up boots feel reminiscent of edgy combat boots, but the less chunky sole makes them feel a bit more pared back. These come in black, brown, white, and burgundy, so you can choose to go classic or colorful.
Midas Lug Sole Chelsea Bootie
Nordstrom Rack
Classic Chelsea boots will never go out of style, just like The Beatles (who were apparently big fans of the shoe style). This leather pair costs less than $60, and it comes in black, brown, and burgundy. The lug sole gives the simple shoe a bit more edge, but it also makes it great for rainy days or uneven pavement.
SOREL Kinetic Conquest Boot
DSW
Hiking boots can be booties, too. With a funky sole and leather details, these hikers feel more designer than woodsy. The lace-up front helps support your feet and ankles, but it also serves as a bit of contrast on the all-black shoe. These are entirely waterproof, so you can trudge through piles of wet leaves or an early snow without any issues.
Blondo Dagger Waterproof Boot
Nordstrom Rack
If Chelsea boots and heeled booties had a baby, this would be their magnificent child. A sleek buckle elevates the simple boot, but you don’t have to fuss with it to get it on (there’s a zipper on the other side that makes it easy to put on and take off). They have a super chunky sole that adds height and traction, and the entire body of the boot is waterproof. Fashion and function, all in one.
