When it comes to readying your wardrobe for the cold-weather season, there’s arguably nothing more fun than adding timeless fall boots to the mix. Fisherman sandals and ugly dad sneakers will always have a special place in our hearts, but it’s time to set those aside and make room for more seasonal options.

Whether you’re ready for a pair of classic combat boots that sprinkle cool girl magic everywhere you step, rain galoshes for cloudy days when you’ll be clomping through puddles, or something fashion-forward to punch up monochrome outfits, Amazon has an amazing selection of under-$75 boots. 

To guide your search, we enlisted the help of stylist Cindy Conroy, who has worked with celebs like Christina Milian. Used to helping her clients find pieces that enhance their wardrobes, she shared her advice on upcoming boot trends, as well as what styles have her attention right now. 

“Cowboy boots are this season’s melodic Rico Suave,” she said. “Like the ‘90s singer, they make you want to dance.” Beyond the Western trend, she also recommends shearling-lined boots as a smart investment. “They’re an unexpected twist to the classic boot that will captivate and reinvigorate your wardrobe,” she said.

Below, check out 15 pairs of fall boots on Amazon, starting at $29.

Shop Under-$75 Fall Boots:

• Blowfish Malibu Moor Boot, $66 (Originally $80)
• Hunter Original Chelsea Boot, $49 (Originally $140)
• Ouepiano Embroidered Western Cowboy Boot, $67
• Dunes Max Moto Boot, $40
• Dirty Laundry Margo Ankle Boot, $62
• Vivianly Block-Heel Ankle Bootie, $51
• Tommy Hilfiger Shyenne Equestrian Boot, $65 
• The Drop Sia Pointed-Toe Western Ankle Boot, $70
• Chegong Knit Chunky-Heel Sock Boot, $29 
• Cape Robbin Nell Glitter Platform Boot, $59
• Dr. Scholl's Shoes So Cozy Ankle Boot, $38 (Originally $100)
• Soda Pilot Chelsea Bootie, $30
• Charles Albert Embroidered Modern Western Cowboy Boot, $50 (Originally $90)
• Circus by Sam Edelman Bethanie Rain Boot, $62 (Originally $120)
• NNG Over-the-Knee Faux-Suede Boot, $47 

Lug boots are worth the investment because they serve double duty — they’re stylish and practical at the same time. This pair from Blowfish Malibu has a chunky rubber sole, making them perfect for rain, sleet, or sludge. Plus, they have double zippers on the back that make them super easy to slip on and off. 

Shop now: $66 (Originally $80); amazon.com

The royals' favorite Hunter rain boots have been marked down 79 percent, which means it’s the right time to scoop them up. Their waterproof rubber construction nicely defends against rainy weather, despite being a short boot. One customer confirmed they wore the boots “in ankle-deep water with zero issues.”

Shop now: $49 (Originally $140); amazon.com

It’s not just supermodels giving the cowboy boot trend a whirl; Conroy is encouraging their clients to try the Western look for themselves, claiming, “The Western motif is at the top of the must-wear list.” This roomy pair has nearly 1,000 five-star ratings from customers who said, “compliments came the whole night” when they wore the boots.

Shop now: $67; amazon.com

Live your best life à la Julia Fox with moto-inspired, vegan leather boots. These are oozing with cool girl, downtown vibes. Wear them with everything in your closet, from long maxi skirts to dresses and even trousers. And according to a shopper, they’re “sharp-looking, well-made, and most importantly, they're super comfortable.”

Shop now: $40; amazon.com 

Wear this elevated Chelsea style with cropped wide-leg trousers and a tucked-in sweater for an instantly chic fall outfit. It features a modest 2-inch heel and a lug sole to give the boot some edge. Plus, a reviewer who usually needs to “break boots in” was able to “wear these all day without any issue.”

Shop now: $62; amazon.com 

A slim boot with an easy block heel is something you’ll reach for time and again because it goes with the full lineup: jeans, trousers, and even sweater dresses. Block heels evenly distribute weight, making them more supportive than a traditional stiletto heel; one shopper even said they wore this pair “for more than six hours and had very little discomfort.”

Shop now: $51; amazon.com

Riding boots are timeless, and one of the most classic ways to wear them is with skinny jeans (point for the skinnies) and an oversized chunky-knit sweater. And since black and brown are the most classic shades, this two-tone pair is especially promising because there’s no need to choose between colors, as a shopper pointed out. 

Shop now: $65; amazon.com 

This snakeskin ankle boot is a definite closet staple because it’s great for punching up your fall looks. If you’re not sure how to style the pointed-toe pair, take a tip from Conroy and focus on outerwear: “Dial up the fun factor by adding a leather trench, and you’re streetwear ready.” 

Shop now: $70; amazon.com 

A classic sock boot is one you’ll reach for frequently because “neutral ankle boots are the perfect canvas for your fall looks,” as Conroy explained. To wear them, “add a peekaboo moment by styling yours with a miniskirt.” This knit pair has a manageable 2.8-inch heel, making them extra wearable. A shopper even confirmed “they look like 'dress-up booties' but feel like slippers.”

Shop now: $29; amazon.com

Every closet needs an entrance-making boot, and this 4-inch-high pair is the one you’ll grab when you want to have a glitter moment. Per a shopper, “I wear them as my statement piece with all-black outfits, and it kills every time.”

Shop now: $59; amazon.com

Conroy is a fan of classic shearling-lined boots like this lace-up pair from Dr. Scholl’s. “Shearling boots are a masterclass in cozy style, and I’m so excited that they’re trending,” she said. This pair offers everything you want from a fall boot: They’re waterproof, faux-shearling-lined, and stylish.

Shop now: $38 (Originally $110); amazon.com

Chunky, white ankle boots went viral two years ago, and they’re nowhere near ready for retirement — you’ll get a ton of use out of them. This best-selling slip-on pair will instantly become your everyday favorite since you can wear them with skirts, trousers, jeans, and even sweats. One shopper said they wore the shoes “while doing tons of walking and [their] feet never, ever hurt.”

Shop now: $30; amazon.com 

This vegan leather cowboy boot has an 11-inch, embroidered shaft that offers major style and ease. “That structured, chunky heel, the intricate stitching, and pointed toe are proof that comfortable fall boots don’t have to skimp on fashion,” Conroy said. In terms of styling, she has more ideas: “A touch of Western paired with a contrasting silk midi dress and chunky jewelry is texture play at its finest.”

Shop now: $50 (Originally $90); amazon.com

Wet conditions are no match for functional wardrobe staples like rain boots, and this pair from Circus by Sam Edelman packs major style points. The rain boots feature an of-the-moment chunky, lug-sole and edgy zippers that make them super easy to get on and off. A reviewer said they “spent all day long with these boots and didn't experience any discomfort whatsoever.”

Shop now: $53 (Originally $120); amazon.com

You’ll hang onto over-the-knee boots for years because they always come back in style. This faux-suede pair is offered with either a 2- or 3-inch heel and boasts over 8,300 five-star ratings. One shopper who has struggled to find over-the-knee boots for wide calves said these “were the perfect fit” since they’re “very easy to put on” and “don’t slide when you wear them.”  

Shop now: $47; amazon.com 

ncG1vNJzZmivp6x7qrrSrbClnV6YvK57xZqqoaGfo3ypwc2tnKtlopa2r3nBqKatq12orq2xjLOYqaifqA%3D%3D