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I had a friend in college who used to say, “Boots and bags—that’s where it’s at, girl!” Kudos to her, because I still subscribe to this theory. Slipping on the right pair of boots will instantly elevate even the simplest outfit and make you feel more fashion-forward. After months of hot, sweaty weather (mostly spent in flip-flops and cut-off denim), I love breaking out my boots and stepping into fall style.
But if you’re shopping on a budget like many of us likely are, then don’t worry! I’ve rounded up some seriously chic boots for fall that are all under $100. From knee-high classics to bold statement-makers, these picks prove you don’t have to spend a fortune to look on-trend this season.
Steve Madden Woodstock Knee High Boot ($90)
Knee-high boots are a fall wardrobe staple for a reason. They add instant polish, provide extra coverage when the weather turns chilly, and look chic with dresses, skirts, or even over skinny jeans. The Woodstock Knee High Boot takes all of that up a notch with its ’70s-inspired silhouette, rounded toe, and retro charm. Elevated on a tall stacked heel, these leather boots are the kind of statement piece that instantly makes any outfit feel pulled together.
Journee Haylinn Medium and Wide Width Booties ($59)
Booties are the perfect in-between option when you want the chic vibe of boots without committing to full height, and this pair hits the sweet spot. The square-toe booties keep it effortlessly stylish with patent vegan leather uppers, and the zipper entry makes them easy to slip on. A block heel plus the 4mm Journee Comfort System Insole ensures they’re comfortable enough to walk around all day.
Athlefit Chelsea Platform Ankle Boots ($39.98)
These Chelsea boots are not only wildly popular (with thousands of glowing reviews on Amazon and a 4.5-star average rating!) but also super affordable. I love that they give you just the right lift with a chunky 2.3-inch heel—high enough to feel stylish, but low enough that you can actually walk around in them. The mix of leather or suede uppers, elastic side panels, and back pull tabs makes them a breeze to slip on and off, while the stretchy sock-like lining keeps your feet comfortable and dry all day. The lug soles are also grippy and supportive, so they work well in rain and icy weather.
Journee Sarah Inside Zip Block Heel Booties ($59)
Some booties are meant to blend in, and some are made to stand out. These definitely fall in the latter camp. The Journee Sarah Booties have such a cool, designer-inspired vibe, thanks to their soft square toe and the bold, patterned block heel that’s different in each color option. I can already picture myself throwing these on with denim (black skinnies, crisp white jeans, or classic blue straight-legs) and letting the boots do all the talking. They sit just above the ankle, so they give your outfit a little extra polish while still being versatile enough to wear on repeat.
Comfortview The Azalia Tall Wide Calf Boot ($96.99)
A pair of well-made, tall black boots will never let you down. I had a similar style years ago that I wore constantly; honestly, it was one of the smartest fashion investments I ever made. The Azalia Boot is that same dependable wardrobe hero, with sleek leather-like uppers, a full inside zipper, and double back elastic panels for a comfortable, custom-feeling fit. The padded insoles and skid-resistant outsole are equally genius touches because you won’t have to sacrifice comfort for style. Overall, they’re versatile enough that they’ll look polished with skinny jeans, but pair just as beautifully with flow-y fall dresses.
VIVAIA Square-Toe Water-Repellent Ankle Boots ($99)
Years of walking through NYC slush and surprise puddles taught me a hard truth: “cute” boots are great, but if they can’t handle bad weather, they’ll be ruined by Thanksgiving. That’s why I love these Riley Pro water-repellent ankle boots from VIVAIA. They strike the perfect balance between elegance and practicality, with a sleek square toe, a chic ankle-height shaft, and soft velvet elastic that adds just the right amount of polish.
DREAM Pairs Laurence Over The Knee Thigh High Chunky Heel Boots ($42.39)
Back in college, my bodycon-dress-wearing self would’ve slipped into these thigh-high boots for a night out without hesitation. Good news is, they’re just as fabulous with more grown-up outfits now. Made with smooth suede or PU and a touch of stretch to hug your legs just right, these over-the-knee boots deliver comfort as well as drama. The chunky block heel and round toe make them surprisingly easy to walk in, while the shoelace tie at the top keeps them perfectly in place. As one Amazon reviewer gushed, “Very sexy and stylish, I get compliments every time I wear them.”
Katy Perry The Wandering Knee High Boot ($89.40)
With their crinkly texture, sleek center seam, and walkable blade heel, these leopard-print stunners are as comfortable as they are daring thanks to a memory foam–cushioned footbed. They’ll be the hero of any outfit, so let them shine—style them with a monochrome look, or mix solid blacks and browns for a chic, fashion-editor vibe. The side zip and elastic gore inset make them easy to wear, but the drama they bring is all you.
Whether you’re into sleek knee-highs, practical weatherproof picks, or bold statement boots, there’s a pair here to match your fall vibe, all without blowing your budget. Step into the season with confidence (and serious style) for under $100!
