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It’s that time: from early fall until late spring — and everything in between — boot season! No matter what the temperature, we always come back to boots, probably because they come in so many different styles and can upgrade any look.

We spoke to stylists and fashion experts to find out their picks for the best waterproof winter boots, slip-on winter boots, ankle boots, winter riding boots and much more. No matter what your style is, there’s a pair of boots that’s a perfect match.

Waterproof winter boots

Coach Women’s Rivington Rain Booties ($95; macys.com)

Coach Women's Rivington Rain Booties
Macy's
Coach Women's Rivington Rain Booties

Brighten up a rainy fall day with these jolly booties, say Stephanie Muehlhausen, senior fashion director for women’s accessories at Macy’s, and Erica Gustafson, the retailer’s associate fashion director for women’s accessories. “We love taking two of our favorite trends, bold color and logo, to add a pop to any rainy-day outfit.”

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Ugg Women’s Classic Mini Clear Boots ($150; macys.com)

Ugg Women's Classic Mini Clear Boots
Macy's
Ugg Women's Classic Mini Clear Boots

Another pick from the Macy’s fashion team, these Ugg mini boots are available in four colors and are lined with the brand’s beloved curly faux shearling — which you can see through the transparent molded design.

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​​Northside Women’s Modesto Snow Boot (starting at $51.62; amazon.com)

​​Northside Women's Modesto Snow Boot
Amazon
​​Northside Women's Modesto Snow Boot

Keep the winter out and the warmth in with these highly rated, well-priced snow boots, which have a fully waterproof seam-sealed construction to keep your feet dry and a gusseted tongue to keep the cold out.

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Sorel Women’s Out N About III Conquest Booties ($130; macys.com)

Sorel Women's Out N About III Conquest Booties
Macy's
Sorel Women's Out N About III Conquest Booties

“Faux Sherpa and shearling have been everywhere this season,” say Muehlhausen and Gustafson. “One of our favorite ways to apply this trend is on our footwear.” These cozy Sorel boots are on-trend and 100% waterproof.

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Dr. Martens Waterproof 1460 ($159.95; zappos.com)

Dr. Martens Waterproof 1460
Zappos
Dr. Martens Waterproof 1460

Always on-trend, these waterproof lace-up boots from Doc Martens combine the combat boot look of the traditional Docs with a twin heat-sealed welt that forms the basis of a waterproof boot and prevents water from getting into the air-cushioned sole.

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Ugg Classic Weather Hiker Boots ($200; macys.com)

Ugg Classic Weather Hiker Boots
Macy's
Ugg Classic Weather Hiker Boots

These cute weather-resistant boots from Ugg are another great example of the comfy shearling trend. Available in black and chestnut, the short boots lace up and have a clasp over the arch to keep them secure. “Whether it’s a hiker or sneaker boot, we are definitely wearing the cozy trend this season!” say Muehlhausen and Gustafson.

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Sam Edelman Laguna Waterproof Boot ($169.95; zappos.com)

Sam Edelman Laguna Waterproof Boot
Zappos
Sam Edelman Laguna Waterproof Boot

You’ll be a dry-footed style star in these waterproof Chelsea boots, says stylist Christina Stein. “Sam Edelman has amazing waterproof booties that are totally on-trend for this year.”

Slip-on winter boots

Circus by Sam Edelman Women’s Darielle Lug Sole Chelsea Boots ($99; macys.com)

Circus by Sam Edelman Women's Darielle Lug Sole Chelsea Boots
Macy's
Circus by Sam Edelman Women's Darielle Lug Sole Chelsea Boots

“Lug soles are one of our favorite trends this fall,” Muehlhausen and Gustafson told us. This well-priced pair comes in 14 fun colors, including ballet pink and porcelain blue. The mighty sole will keep you confident and comfy on icy days and cold nights.

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Cool Planet by Steve Madden Women’s Cyclone Cold-Weather Hiker Booties ($109; macys.com)

Cool Planet by Steve Madden Women's Cyclone Cold-Weather Hiker Booties
Macy's
Cool Planet by Steve Madden Women's Cyclone Cold-Weather Hiker Booties

These cozy booties, recommended by Muehlhausen and Gustafson, come in tan and black and have a bulky lug sole to get you safely across treacherous ice this winter. The faux shearling will keep you warm and looking cute.

Ankle boots

Steve Madden Women’s Amulet Embellished Lug Sole Booties ($129; macys.com)

Steve Madden Women's Amulet Embellished Lug Sole Booties
Macy's
Steve Madden Women's Amulet Embellished Lug Sole Booties

Another fun lug sole, these booties come in four colors, including our favorite (and Muehlhausen and Gustafson’s) winter white, which has a stylish chain embellishment across the front — giving these well-priced boots a major upgrade.

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Inc International Concepts Women’s Reanna Chain Dress Booties ($119.50; macys.com)

Inc International Concepts Women's Reanna Chain Dress Booties
Macy's
Inc International Concepts Women's Reanna Chain Dress Booties

“Our favorite dress boots this season have chain, western and knit details!” Muehlhausen and Gustafson told us. Get in on the trend in this sexy taupe pair that will dress up a boho look for a night out.

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Steve Madden Women’s Tackle Block-Heel Knit Sock Booties ($129; macys.com)

Steve Madden Women's Tackle Block-Heel Knit Sock Booties
Macy's
Steve Madden Women's Tackle Block-Heel Knit Sock Booties

“A great way to elevate any outfit in the fall,” say Muehlhausen and Gustafson. The unique heel on these boots lifts the artful mix of leather and ribbed knit to a chic evening look. We love this in bone or burgundy.

Winter riding boots

Stuart Weitzman 5050 Ultralift Over the Knee Boot ($750; nordstrom.com)

Stuart Weitzman 5050 Ultralift Over the Knee Boot
Nordstrom
Stuart Weitzman 5050 Ultralift Over the Knee Boot

Give your riding boots a more modern look with a lug sole, says Stein. “In some situations a riding boot is necessary, but these days the lug sole boot is the winner.” She recommends this boot from Stuart Weitzman to stay chic and warm.

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Vince Camuto Women’s Felinda Dress Boots ($229; macys.com)

Vince Camuto Women's Felinda Dress Boots
Macy's
Vince Camuto Women's Felinda Dress Boots

For a sleeker, dressier look, try these dramatic dress boots that are “elevated” by their “chain detail,” explain Muehlhausen and Gustafson. Absolutely fabulous in blood red, the boots are also available in black and white.

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Sam Edelman Penny 2 Wide Calf Leather Riding Boot (starting at $75.97; zappos.com)

Sam Edelman Penny 2 Wide Calf Leather Riding Boot
Zappos
Sam Edelman Penny 2 Wide Calf Leather Riding Boot

Wide calves? Not a problem with these stylish riding boots available in black or brown. Not only are they well-priced, they have the western touches that all of our stylists agree are of-the-moment, and the low heel is perfect for running around on a fall afternoon.