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It’s that time: from early fall to late spring – and everything in between – boot season! No matter the temperature, we always return to shoes, perhaps because they come in so many different styles and can upgrade any look.
We spoke to designers and fashion experts to find out their picks for the best waterproof winter boots, winter slip-ons, ankle boots, winter riding boots, and more. No matter your style, there is a pair of shoes that fit just right.
Coach Women’s Rivington Rain Boots ($95; macys.com)
Brighten up a rainy day with these fun socks, says Stephanie Mulhausen, senior fashion director for women’s accessories at Macy’s, and Erika Gustafson, associate fashion director for the women’s accessories retailer. “We love taking two of our favorite trends, the bold color and the logo, to accent any rainy day outfit.”
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Women’s Classic Small Clear Ugg Boots ($150; macys.com)
Another pick from Macy’s fashion team, these mini Ugg boots are available in four colors and are lined with the brand’s beloved crinkle fabric—which you can see through the sheer molded design.
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Northside Women’s Modesto Snow Boot (starting at $51.62); amazon.com)
Keep the winter and warm with these highly rated and well-priced snow boots, which feature sealed construction and fully waterproof to keep your feet dry and a split tongue to keep out the cold.
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Sorel Women’s Out N About III Conquest Booties ($130; macys.com)
“Faux Sherpa and shearling have been everywhere this season,” Mulhausen and Gustafson say. “One of our favorite ways to apply this trend is on our shoes.” These comfortable Sorel shoes are on-trend and 100% waterproof.
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Martens Waterproof 1460 ($159.95; zappos.com)
These Doc Martens waterproof boots combine the look of a traditional Docs combat boot with a heat-sealed double layer that forms the basis of the waterproof boot and prevents water from reaching the air-cushioned sole.
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UG Classic Weather Hiker Boot ($200; macys.com)
These cute, weatherproof boots from Ugg are another great example of the comfy shearling trend. Available in black and chestnut, this short boot features a lace-up upper with a bow closure to keep it secure. “Whether it’s a hiking boot or a sneaker, we’re definitely wearing the comfy trend this season!” Mulhausen and Gustafson say.
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Sam Edelman Laguna Waterproof Boot $169.95; zappos.com)
The designer says you’ll be a dry star in these waterproof Chelsea boots Christina Stein. “Sam Edelman has great waterproof shoes that are totally on-trend this year.”
Circus Women’s Darielle Lug Sole Chelsea Boot from Sam Edelman ($99; macys.com)
“The lug sole is one of our favorite trends this fall,” Mulhausen and Gustafson told us. This well-priced pair comes in 14 fun colors, including ballet pink and ceramic blue. The sturdy sole will keep you confident and comfortable on icy days and chilly nights.
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Cool Planet by Steve Madden Women’s Cyclone Cold-Weather Hiker Booties ($109; macys.com)
These comfy socks, recommended by Muehlhausen and Gustafson, come in brown and black and have a massive sole to get you safely through treacherous ice this winter. Shearling faux will keep you warm and looking cute.
Steve Madden Women’s Amulet Embellished with Lug Sole Socks ($129; macys.com)
Another fun sole, these booties come in four colors, including our favorite winter white (and Mühlhausen and Gustafson), which features a stylish chain trim on the front side—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)
“Our favorite dress shoes this season have chain, western, and knit details!” Mulhausen and Gustafson told us. Hit the trend with this sexy dark pair that will elevate your boho look for a night out.
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Steve Madden Women’s Knit Heeled Shoes ($129; macys.com)
“A great way to elevate any outfit for fall,” Mulhausen and Gustafson say. The unique heel of this boot elevates the exquisite blend of leather and ribbed knit for a chic evening look. We love this in bone or burgundy.
Stuart Weitzman 5050 Ultralift Over the Knee Boot ($750; nordstrom.com)
Give your riding boots a more modern look with a lug sole, says Stein. “In some cases, a riding shoe is necessary, but these days a lobster shoe is a winner.” She recommends these shoes from Stuart Weitzman to stay stylish and warm.
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Vince Camuto Felinda women’s shoes ($229; macys.com)
For a more elegant and elegant look, try these dramatic dress shoes “high” by “chain detailing,” as explained by Mulhausen and Gustafsson. The shoes are absolutely gorgeous in blood red, and they are also available in black and white.
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Sam Edelman Penny 2 Wide Calf Leather Riding Boots (starting at $75.97); zappos.com)
wide calves? Not a problem with these stylish riding boots available in black or brown. Not only are they well priced, they have western touches that all of our stylists agree on, and the low heels are perfect for afternoon jogging.
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