11 Types of Fall Boots and How To Wear Them

Despite the fact that Labor Day is behind us and Pumpkin Spice Lattes came early this year, the official first day of autumn isn't until September 23rd, which gives us a couple more weeks to consider the many ways we want to embrace fall to the fullest.

Like, for example, making sure that everything you eat taste like pumpkin, clearing space in your schedule for new seasons of your favorite television shows, and embracing all of the goodness that is fall fashion. From cool leather jackets to cozy blanket coats, fall has to be my favorite season when it comes to clothing. After a summer full of shorts and sundresses, swaddling myself in cozy knits is a welcome change of pace. 

And because wool knits worn with flip flops simply don't make sense, let's talk about the fall footwear of choice: boots! Whether you prefer slouchy suedes, structured riding boots, or a pair that pulls up past you knees, there's a pair (or two) out there for everyone. Here are 11 popular styles with tips on how to wear each. So snuggle up with your PSL and peruse some seasonal style inspiration.

Rain Bootie

These snug little rain booties are one of this season’s hottest accessories. They’re small but mighty and are sure to keep your feet dry on sprinkly fall days. 

Chelsea Rain Boots, $30, Amazon

Chunky Suede Bootie

Meghan Blalock put it perfectly for StyleCaster: “Every woman absolutely needs a pair of stacked booties in her closet. Whether it’s black or brown, these are best in staple colors so you can wear them with just about any fall look.” The thick heel will offer some more support for your feet (compared to a stiletto) and will look beautiful paired with an oversized knit sweater or fall flannel.

Jeffrey Campbell Hanger Suede Raw Booties In Taupe, $155, shopbop

Cutout Bootie

Cutouts add a fun twist to traditional booties. “Rock stylish socks underneath to change up the look,” Marianne Dabir tells Teen Vogue. For this particular pair, I recommend thin, slouchy socks.

Western Cutout Booties, $37, forever21

Over-The-Knee Suede Boots

Finding a good pair of over-the-knee boots can be tricky, but once you find the right pair you’ll be happy you have them. “Whether equestrian and flat or with a slight heel, a high boot lends just the right amount of drama, while remaining endearingly classic,” Kerry Pieri tells Harpers BazaarI invested in a pair of these classic, skin-hugging 5050 boots from Stuart Weitzman and I can honestly say that they’re worth every penny. They’re pricey, but I’ve been wearing the same pair for the past 3 years.  

The 5050 Boot In Nice Blue Suede, $391, Amazon

Lace-Up Combat Boots

“Combat boots are a crazy-comfortable way to make an edgy statement,” Dabir tells Teen Vogue. Wear them with your favorite skinny jeans to accentuate the shoe’s substantial size. “Whether you’re into pretty prints, bright colors, or just plain black, you’ll want a pair of these in your closet this fall. Your wardrobe — and your feet! — will thank you!”

Women’s 1460 In White Portland Rose, $130, drmartens

Bright Boots

When I think of fall fashion, I think of transitioning from bright summer whites and neons to mellow earth tones, but this doesn’t have to be the case. Keep the color going all year round. “You absolutely must have a colored boot in your wardrobe,” Blalock told StyleCaster. “Precisely what color is up to you and what blows your proverbial skirt up, but you need something that will up the ‘wow’ factor of your outfit instantly.” These shocking blue booties have the perfect heel for a night out on the town.

Bagatt Shoe Boot, $147, yooxcom

Fringe Booties

The festival days of summer are over, but that doesn’t mean you have to pack up the fringe. Add a little swish to your step with these little brown booties from Anthropologie. They’d look lovely with thick knit stockings and a bohemian-style dress.  

Fringe Flutter Booties, $150, Anthropologie

Lace-Up Rain Boots

Brighten up a rainy day with a pair of colorful rain boots. I love that this sunshine-y yellow pair has laces up the front, which adds a little more intrigue than basic solid wellies. Plus, they’ll look beautiful against a backdrop of fall leaves on the pavement.  

Rain Boot Long Classic With Laces, $156, Ilsejacobsen

Snake Skin Bootie

Much like the LBD, the LBB (little black bootie) is a wardrobe essential. “A black bootie with a slim heel and subtly pointed toe can take the place of pumps in cooler weather and work with everything from skirts to denim,” Pieri tells Harpers Bazaar. When pairing with a skirt, layer on black tights for a seriously sexy look.

Petty Skin Bootie, $75, Amazon

Riding Boot

Riding boots are incredibly versatile, but my favorite way to wear them is over dark wash skinny jeans with a chambray shirt for an ensemble that makes me feel like I’m in the Wild West. And since oxblood is the color of the moment, I’ve picked out this pair, which also happens to be pretty budget-friendly.  

Bamboo Belted Flat Knee-High Riding Boots, $43, Charlotterusse

Slouchy Suede Boot

No matter tall or short, I love the look of a slouchy suede boot. They just look so cozy and, after all, isn’t that the fun of fall fashion? Snuggling up after the summer heat fades?

Steve Madden Winner Western Slouch Boot, $26, Nordstromrack